CN108948034A - 一种色满桥环异吲哚酮及其制备方法 - Google Patents
一种色满桥环异吲哚酮及其制备方法 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract description 6
- XTBAPWCYTNCZTO-UHFFFAOYSA-N 1H-isoindolone Natural products C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 title 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims abstract description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000001914 filtration Methods 0.000 claims abstract description 19
- AETKQQBRKSELEL-ZHACJKMWSA-N 2'-hydroxychalcone Chemical compound OC1=CC=CC=C1C(=O)\C=C\C1=CC=CC=C1 AETKQQBRKSELEL-ZHACJKMWSA-N 0.000 claims abstract description 11
- 238000004440 column chromatography Methods 0.000 claims abstract description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- UCYRAEIHXSVXPV-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)indiganyl trifluoromethanesulfonate Chemical compound [In+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F UCYRAEIHXSVXPV-UHFFFAOYSA-K 0.000 claims description 2
- HIYUMYXSGIKHHE-UHFFFAOYSA-M bismuth trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F HIYUMYXSGIKHHE-UHFFFAOYSA-M 0.000 claims description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- PGJLOGNVZGRMGX-UHFFFAOYSA-L iron(2+);trifluoromethanesulfonate Chemical compound [Fe+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PGJLOGNVZGRMGX-UHFFFAOYSA-L 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 claims description 2
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims description 2
- ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 claims description 2
- -1 1,2-dichloroethane alkanes Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000006845 Michael addition reaction Methods 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 47
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QMGHHBHPDDAGGO-IIWOMYBWSA-N (2S,4R)-1-[(2S)-2-[[2-[3-[4-[3-[4-[[5-bromo-4-[3-[cyclobutanecarbonyl(methyl)amino]propylamino]pyrimidin-2-yl]amino]phenoxy]propoxy]butoxy]propoxy]acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound CN(CCCNC1=NC(NC2=CC=C(OCCCOCCCCOCCCOCC(=O)N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)NCC3=CC=C(C=C3)C3=C(C)N=CS3)C(C)(C)C)C=C2)=NC=C1Br)C(=O)C1CCC1 QMGHHBHPDDAGGO-IIWOMYBWSA-N 0.000 description 1
- IZGDXVLRMHXOJV-SFHVURJKSA-N (3s)-4-[2-[2-(4-fluoro-3-methylphenyl)-4-methyl-6-propan-2-ylphenyl]ethyl-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound CC(C)C1=CC(C)=CC(C=2C=C(C)C(F)=CC=2)=C1CCP(O)(=O)C[C@@H](O)CC(O)=O IZGDXVLRMHXOJV-SFHVURJKSA-N 0.000 description 1
- RTTUBUXMNUJHRR-DXRVJIQQSA-N (3s)-4-[[(e)-2-[1-(4-fluorophenyl)-3-propan-2-ylindol-2-yl]ethenyl]-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound C12=CC=CC=C2C(C(C)C)=C(\C=C\P(O)(=O)C[C@@H](O)CC(O)=O)N1C1=CC=C(F)C=C1 RTTUBUXMNUJHRR-DXRVJIQQSA-N 0.000 description 1
- AOSODOHQJJPEAM-VUVZNRFTSA-N (3s)-4-[[(e)-2-[3'-(4-fluorophenyl)spiro[cyclopentane-1,1'-indene]-2'-yl]ethenyl]-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound OC(=O)C[C@H](O)CP(O)(=O)\C=C\C1=C(C=2C=CC(F)=CC=2)C2=CC=CC=C2C11CCCC1 AOSODOHQJJPEAM-VUVZNRFTSA-N 0.000 description 1
- WHQUHTXULUACFD-KRWDZBQOSA-N (3s)-4-[[2-(4-fluoro-3-methylphenyl)-4-methyl-6-propan-2-ylphenyl]methoxy-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound CC(C)C1=CC(C)=CC(C=2C=C(C)C(F)=CC=2)=C1COP(O)(=O)C[C@@H](O)CC(O)=O WHQUHTXULUACFD-KRWDZBQOSA-N 0.000 description 1
- MNIPVWXWSPXERA-IDNZQHFXSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecanoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)CCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 MNIPVWXWSPXERA-IDNZQHFXSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BOOYHBPHFVNWNH-OAHLLOKOSA-N 1-tert-butyl-6-[[(1R)-1-(4-chlorophenyl)ethyl]amino]-5-[(4-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C[C@H](C1=CC=C(C=C1)Cl)NC2=NC3=C(C=NN3C(C)(C)C)C(=O)N2CC4=CC=C(C=C4)F BOOYHBPHFVNWNH-OAHLLOKOSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 1
- JWHYSEDOYMYMNM-QGZVFWFLSA-N 2-[4-[(2r)-2-ethoxy-3-[4-(trifluoromethyl)phenoxy]propyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound C([C@@H](OCC)CSC=1C=C(C)C(OCC(O)=O)=CC=1)OC1=CC=C(C(F)(F)F)C=C1 JWHYSEDOYMYMNM-QGZVFWFLSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126650 Compound 3f Drugs 0.000 description 1
- KGPGFQWBCSZGEL-ZDUSSCGKSA-N GSK690693 Chemical compound C=12N(CC)C(C=3C(=NON=3)N)=NC2=C(C#CC(C)(C)O)N=CC=1OC[C@H]1CCCNC1 KGPGFQWBCSZGEL-ZDUSSCGKSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- HFIVLLBFACNAFN-UHFFFAOYSA-N [1-amino-2-[2-(4-methoxyphenyl)ethylamino]ethyl]phosphonic acid Chemical compound COc1ccc(CCNCC(N)P(O)(O)=O)cc1 HFIVLLBFACNAFN-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- MUTCAPXLKRYEPR-ITWZMISCSA-N methyl (e,3r,5s)-7-[4-bromo-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyhept-6-enoate Chemical compound COC(=O)C[C@H](O)C[C@H](O)\C=C\N1C(C(C)C)=C(Br)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 MUTCAPXLKRYEPR-ITWZMISCSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明公开了一种色满桥环异吲哚酮及其制备方法，属于有机合成技术领域。本发明通过将异吲哚酮和邻羟基查尔酮加在乙腈溶剂中，以对甲苯磺酸为催化剂，在35 oC的温度下发生Michael加成/缩合/环化串联反应来制备色满桥环异吲哚酮。本发明避免分离中间体，反应完全后，通过过滤或柱色谱即可拿到纯品。本发明具有反应条件温和、操作简单、底物范围广等优点。
Description
技术领域
本发明属于有机合成领域，具体涉及一种色满桥环异吲哚酮及其制备方法。
背景技术
异吲哚酮是很多天然产物和药物的核心骨架，具有重要的生理活性。因此，发展高效的合成异吲哚酮的方法或者对异吲哚酮母核进行化学修饰具有十分重要的理论意义和现实价值。开展这方面的研究，不但丰富了异吲哚酮的种类，同时还为药物筛选提供更多的候选分子。目前对异吲哚酮母核的结构修饰主要集中于烷基化反应(Tetrahedron,2017,73,819.)、环化串联反应(Tetrahedron Lett.,2015,21,2787.)和螺环化反应(Tetrahedron,2008,64,3505.),这些反应构建的分子要么仅仅在异吲哚酮的基础上新建了一个单环形成环结构，要么仅仅是简单的烷基化，而在异吲哚酮酮骨架的基础上构建桥环目前还未见报道。因此，开发新的合成策略用以合成结构新型的桥环异吲哚酮具有很重要的意义。
发明内容
针对现有技术中存在的问题，本发明提供一种结构新型色满桥环异吲哚酮及其制备方法，操作简单、反应条件温和、且目标产物容易分离。
为解决上述技术问题，本发明采用以下技术方案：
一种色满桥环异吲哚酮，其结构式如下：
其中，R1为烷基；R2为芳基或烷基；R3为H、卤原子或烷基。
所述的色满桥环异吲哚酮的制备方法，将异吲哚酮和邻羟基查尔酮，在有机溶剂中，酸的存在下，25-100℃反应6-72h，薄层色谱跟踪反应至完全，反应结束后，通过用布氏漏斗过滤或者柱色谱分离纯化，得目标产物，其反应通式如下：
其中，R1为烷基；R2为芳基或烷基；R3为H、卤原子或烷基。
所述的酸为Lewis酸或质子酸。
所述Lewis酸为三氟甲磺酸铜、三氟甲磺酸锌、三氟甲磺酸钇、三氟甲磺酸铟、三氟甲磺酸铋、三氟甲磺酸钪、三氟甲磺酸铁、三氯化铁或溴化铜；质子酸为三氟甲磺酸、三氟醋酸、甲磺酸、对甲苯磺酸、醋酸或硫酸。
所述的酸的物质的量为邻羟基查尔酮物质的量的20％。
所述的有机溶剂为乙腈、甲苯、甲醇、氯仿、二氯甲烷、1,2-二氯乙烷、四氢呋喃、1,4-二氧六环或乙酸乙酯。
所述的有机溶剂为乙腈。
所述反应温度为35℃。
所述异吲哚酮与邻羟基查尔酮的摩尔比为1:1-2:1。
所述异吲哚酮与邻羟基查尔酮的摩尔比为1.1:1。
本发明的有益效果：本发明通过将异吲哚酮和邻羟基查尔酮加在乙腈溶剂中，以对甲苯磺酸为催化剂，在35℃的温度下发生Michael加成/缩合/环化串联反应来制备色满桥环异吲哚酮。本发明在异吲哚酮母核的基础上，引入了色满这一生理活性骨架，同时还构建了一个桥环结构，中间产物不需分离纯化，且目标产物容易分离；操作简单、反应条件温和，收率高达99％。
附图说明
图1为实施例1化合物3a的1H NMR图；
图2为实施例1化合物3a的13C NMR图；
图3为实施例1化合物3a的X-射线单晶衍射图。
具体实施方式
下面结合具体实施例，对本发明做进一步说明。应理解，以下实施例仅用于说明本发明而非用于限制本发明的范围，该领域的技术熟练人员可以根据上述发明的内容作出一些非本质的改进和调整。
实施例1
色满桥环异吲哚酮3a的制备：往10mL硬质玻璃反应试管中，加入异吲哚酮1a(0.22mmol，45.2mg)，邻羟基查尔酮2a(0.20mmol，44.9mg)，对甲苯磺酸(6.9mg，0.04mmol)，然后加入1mL乙腈，混合物在35℃搅拌24h。反应完全后，过滤，滤饼即为目标化合物3a(白色固体，收率97％)。
所得化合物3a的核磁共振氢谱、碳谱、红外以及高分辨质谱数据如下:
1H NMR(400MHz,CDCl3),δ7.94(d,J＝8.0Hz,2H),7.63(d,J＝8.0Hz,1H),7.58(d,J＝8.0Hz,1H),7.51-7.45(m,3H),7.43-7.39(m,1H),7.33(t,J＝8.0Hz,1H),6.98(t,J＝8.0Hz,1H),6.87(d,J＝8.0Hz,1H),6.84(d,J＝8.0Hz,1H),6.63(t,J＝8.0Hz,1H),4.35-4.29(m,1H),4.22-4.16(m,1H),4.09(s,1H),2.71-2.63(m,2H),1.29(t,J＝8.0Hz,3H)；13CNMR(100MHz,CDCl3)δ170.9,169.6,152.2,141.8,138.6,133.6,132.7,129.6,129.1,129.0,128.7,128.5,126.3,124.6,123.1,121.5,121.0,117.4,93.8,84.5,62.6,44.0,43.9,14.1.IR(KBr)ν3060,2990,1720,1304,1240,756cm-1.HRMS(ESI)calcd for C26H22NO4[M+H]+412.1543,found412.1542.
化合物3b-w的制备方法同化合物3a，投料比与化合物3a相同，可得到化合物3b-w，反应产率见表1，但需要强调的是本发明的化合物并不局限于表1中所示化合物。
表1：含有不同取代基的色满桥环异吲哚酮的制备结果
化合物3b(白色固体，93％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.83(d,J＝8.0Hz,2H),7.74(d,J＝8.0Hz,1H),7.62(t,J＝8.0Hz,1H),7.52-7.41(m,5H),7.03(d,J＝8.0Hz,1H),6.99(t,J＝8.0Hz,1H),6.76(d,J＝8.0Hz,1H),6.65(t,J＝8.0Hz,1H),4.18(d,J＝4.0Hz,1H),3.81(s,3H),2.72-2.63(m,2H)；13C NMR(100MHz,DMSO-d6)δ170.5,168.5,151.7,141.7,138.7,133.3,132.8,129.9,129.5,129.0,128.5,128.3,126.1,123.8,123.7,121.9,120.9,116.5,93.2,84.1,53.7,43.3,42.7.IR(KBr)ν3422,1722,1243,755cm-1.HRMS(ESI)calcd for C25H20NO4[M+H]+398.1387,found 398.1390.
化合物3c(白色固体，95％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.83(d,J＝4.0Hz,2H),7.74(d,J＝8.0Hz,1H),7.62(t,J＝8.0Hz,1H),7.51-7.41(m,5H),7.03(d,J＝4.0Hz,1H),6.99(t,J＝8.0Hz,1H),6.75(d,J＝8.0Hz,1H),6.65(t,J＝8.0Hz,1H),4.24-4.09(m,3H),2.73(d,J＝12.0Hz,1H),2.61(dd,J1＝J2＝4.0Hz,1H),1.67-1.59(m,2H),0.83(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.5,151.7,141.8,138.7,133.3,132.9,129.9,129.6,128.9,128.6,128.2,126.2,123.8,123.6,121.9,120.9,116.5,93.3,84.2,67.8,43.3,42.7,21.4,10.2.IR(KBr)ν3424,1719,1234,763cm- 1.HRMS(ESI)calcd for C27H24NO4[M+H]+426.1700,found 426.1697.
化合物3d(白色固体，69％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.85(d,J＝4.0Hz,2H),7.74(d,J＝8.0Hz,1H),7.62(t,J＝8.0Hz,1H),7.52-7.38(m,5H),6.99(q,J＝8.0Hz,2H),6.76(d,J＝8.0Hz,1H),6.65(t,J＝8.0Hz,1H),5.07-5.00(m,1H),4.15(d,J＝4.0Hz,1H),2.71(d,J＝12.0Hz,1H),2.58(dd,J1＝J2＝4.0Hz,1H),1.24(d,J＝4.0Hz,3H),1.20(d,J＝4.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.4,168.4,151.7,141.7,138.7,133.2,132.9,129.8,129.4,128.9,128.5,128.2,126.1,123.7,123.5,121.9,120.9,116.5,93.2,84.1,70.2,43.4,42.8,21.2(2C).IR(KBr)ν3422,2982,1720,1237,1108,754cm-1.HRMS(ESI)calcd for C27H24NO4[M+H]+426.1700,found 426.1697.
化合物3e(白色固体，93％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.89-7.85(m,2H),7.75(d,J＝8.0Hz,1H),7.63(t,J＝8.0Hz,1H),7.46(d,J＝8.0Hz,1H),7.42(d,J＝8.0Hz,1H),7.34(d,J＝8.0Hz,2H),7.04-6.97(m,2H),6.76(d,J＝8.0Hz,1H),6.65(t,J＝8.0Hz,1H),4.34-4.30(m,1H),4.22-4.16(m,2H),2.73(d,J＝12.0Hz,1H),2.63(dd,J1＝J2＝4.0Hz,1H),1.24(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.0,168.5,151.6,141.7,135.1,133.4,132.7,129.9,129.5,129.0,128.5,128.4,123.8,123.7,121.8,121.0,116.5,115.1(d,J＝19.0Hz,1C),92.8,84.1,62.5,43.2,42.8,13.9.IR(KBr)ν3063,2991,1720,1304,1239,1152,754cm-1.HRMS(ESI)calcd for C26H21FNO4[M+H]+430.1449,found 430.1447.
化合物3f(白色固体，99％收率，通过过滤分离纯化)：1H NMR(400MHz,CDCl3),δ7.89(d,J＝12.0Hz,2H),7.64(d,J＝8.0Hz,1H),7.56(d,J＝4.0Hz,1H),7.49(t,J＝8.0Hz,1H),7.44(d,J＝8.0Hz,2H),7.33(t,J＝8.0Hz,1H),6.98(t,J＝8.0Hz,1H),6.85(t,J＝8.0Hz,2H),6.64(t,J＝8.0Hz,1H),4.37-4.30(m,1H),4.24-4.16(m,1H),4.09(s,1H),2.65(t,J＝12.0Hz,2H),1.30(t,J＝8.0Hz,3H)；13C NMR(100MHz,CDCl3)δ170.6,169.6,152.0,141.7,137.3,134.6,133.4,132.8,129.6,129.2,129.0,128.6,127.8,124.6,123.2,121.4,121.2,117.3,93.2,84.3,62.6,43.9,43.8,14.1.IR(KBr)ν3059,2987,1720,1301,1236,751cm-1.HRMS(ESI)calcd for C26H21ClNO4[M+H]+446.1154,found 446.1151.
化合物3g(白色固体，99％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.89-7.71(m,5H),7.63(t,J＝8.0Hz,1H),7.46(d,J＝4.0Hz,1H),7.41(t,J＝8.0Hz,1H),7.04-6.97(m,2H),6.76(d,J＝8.0Hz,1H),6.66(t,J＝8.0Hz,1H),4.36-4.28(m,1H),4.24-4.16(m,2H),2.73-2.62(m,2H),1.24(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.9,168.5,151.5,141.7,138.2,133.4,132.7,131.3,129.9,129.6,129.0,128.4,123.8,123.7,122.0,121.8,121.1,116.5,92.7,84.0,62.6,43.1,42.8,13.9.IR(KBr)ν3058,2984,1718,1301,1235,753cm-1.HRMS(ESI)calcd for C26H21BrNO4[M+H]+490.0649,found490.0647.
化合物3h(白色固体，99％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.72(t,J＝8.0Hz,3H),7.62(t,J＝8.0Hz,1H),7.45(d,J＝4.0Hz,1H),7.40(t,J＝8.0Hz,1H),7.29(d,J＝8.0Hz,2H),7.02-6.96(m,2H),6.75(d,J＝8.0Hz,1H),6.64(t,J＝8.0Hz,1H),4.35-4.22(m,1H),4.22-4.14(m,2H),2.67(d,J＝12.0Hz,1H),2.58(dd,J1＝J2＝4.0Hz,1H),2.37(s,3H),1.23(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.0,168.5,151.8,141.7,137.9,135.9,133.2,132.9,129.9,129.5,128.9,128.7,126.1,123.8,123.6,121.9,120.9,116.5,93.2,84.1,62.5,43.4,42.8,20.8,13.9.IR(KBr)ν3052,2986,1719,1235,1150,753cm-1.HRMS(ESI)calcd for C27H24NO4[M+H]+426.1700,found426.1696.
化合物3i(白色固体，97％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.75-7.72(m,3H),7.61(t,J＝8.0Hz,1H),7.45(d,J＝4.0Hz,1H),7.40(t,J＝8.0Hz,1H),7.05-6.95(m,4H),6.74(d,J＝8.0Hz,1H),6.64(t,J＝8.0Hz,1H),4.35-4.27(m,1H),4.22-4.16(m,1H),4.14(d,J＝4.0Hz,1H),3.81(s,3H),2.68(d,J＝12.0Hz,1H),2.58(dd,J1＝J2＝4.0Hz,1H),1.23(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.5,159.5,151.9,141.7,133.2,132.9,130.8,129.9,129.5,128.9,127.5,123.7,123.6,121.9,120.9,116.5,113.5,93.2,84.1,62.4,55.2,43.4,42.8,13.9.IR(KBr)ν3437,2998,1726,1243,1169,1025,749cm-1.HRMS(ESI)calcd for C27H24NO5[M+H]+442.1649,found442.1645.
化合物3j(白色固体，87％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.74(dd,J1＝J2＝4.0Hz,3H),7.62(t,J＝8.0Hz,1H),7.46(d,J＝4.0Hz,1H),7.41(t,J＝8.0Hz,1H),7.36(d,J＝8.0Hz,2H),6.99(q,J＝8.0Hz,2H),6.74(d,J＝8.0Hz,1H),6.64(t,J＝8.0Hz,1H),4.35-4.27(m,1H),4.23-4.17(m,1H),4.15(d,J＝4.0Hz,1H),3.01-2.91(m,1H),2.70-2.58(m,2H),1.25(dd,J1＝J2＝8.0Hz,9H)；13C NMR(100MHz,DMSO-d6)δ170.0,168.5,151.8,148.8,141.7,136.2,133.2,132.9,129.9,129.5,128.9,126.2,126.1,123.8,123.6,121.9,120.9,116.5,93.3,84.1,62.5,43.4,42.8,33.3,23.9,13.1.IR(KBr)ν3425,2964,1721,1298,1236,752cm-1.HRMS(ESI)calcd for C29H28NO4[M+H]+454.2013,found 454.2010.
化合物3k(白色固体，82％收率，通过柱色谱分离纯化(石油醚：乙酸乙酯＝5:1))：1H NMR(400MHz,DMSO-d6),δ7.74(d,J＝12.0Hz,1H),7.63-7.53(m,3H),7.46-7.37(m,2H),7.24(d,J＝12.0Hz,1H),6.99(q,J＝8.0Hz,2H),6.75(d,J＝8.0Hz,1H),6.63(t,J＝8.0Hz,1H),4.38-4.27(m,1H),4.22-4.11(m,2H),2.65(d,J＝16.0Hz,1H),2.56(dd,J1＝J2＝4.0Hz,1H),2.28(d,J＝4.0Hz,6H),1.23(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.2,168.5,151.8,141.7,136.6,136.3,135.9,133.3,133.0,129.9,129.6,129.3,129.0,127.1,123.8,123.6(2C),121.9,120.9,116.5,93.3,84.1,62.5,43.6,42.8,19.7,19.2,14.0.IR(KBr)ν3431,2979,1723,1250,751cm-1.HRMS(ESI)calcd for C28H26NO4[M+H]+440.1856,found 440.1854.
化合物3l(白色固体，97％收率，通过柱色谱分离纯化(石油醚：乙酸乙酯＝2:1))：1H NMR(400MHz,DMSO-d6),δ7.74(d,J＝8.0Hz,1H),7.62(t,J＝8.0Hz,1H),7.46(d,J＝4.0Hz,1H),7.39(dd,J1＝J2＝8.0Hz,3H),7.05(d,J＝8.0Hz,1H),6.99(q,J＝8.0Hz,2H),6.76(d,J＝8.0Hz,1H),6.64(t,J＝8.0Hz,1H),4.33-4.17(m,2H),4.15(d,J＝4.0Hz,1H),3.81(d,J＝4.0Hz,6H),2.71(d,J＝12.0Hz,1H),2.59(dd,J1＝J2＝4.0Hz,1H),1.21(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.5,151.8,149.0,148.4,141.7,133.2,132.9,131.2,129.8,129.5,128.9,123.8,123.6,121.9,120.9,118.6,116.5,111.4,110.2,93.2,84.1,79.2,62.5,55.6,43.4,42.8,13.9.IR(KBr)ν3420,2947,1718,1234,1022,757cm-1.HRMS(ESI)calcd for C28H26NO6[M+H]+472.1755,found 472.1758.
化合物3m(白色固体，33％收率，通过柱色谱分离纯化(石油醚：乙酸乙酯＝4:1))：1H NMR(400MHz,DMSO-d6),δ8.10(s,1H),7.76(d,J＝8.0Hz,1H),7.64-7.42(m,6H),6.99(dd,J1＝J2＝8.0Hz,2H),6.66(dd,J1＝J2＝8.0Hz,2H),4.23-4.12(m,3H),3.26(d,J＝16.0Hz,1H),2.56(d,J＝16.0Hz,1H),1.15(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.8,168.7,151.4,141.8,134.7,133.5,132.6,131.8,131.1,130.9,130.8,130.0,129.7,129.1,127.0,123.9,123.7,122.0,121.0,116.4,93.9,83.7,62.5,42.3,13.9,onecarbon missing in the aliphatic region.IR(KBr)ν3423,2975,1716,1245,1027,755cm-1.HRMS(ESI)calcd for C26H21ClNO4[M+H]+446.1154,found 446.1152.
化合物3n(白色固体，30％收率，通过柱色谱分离纯化(石油醚：乙酸乙酯＝4:1))：1H NMR(400MHz,DMSO-d6),δ8.12(d,J＝8.0Hz,1H),7.77(d,J＝8.0Hz,2H),7.64(t,J＝8.0Hz,1H),7.55-7.38(m,4H),6.99(q,J＝8.0Hz,2H),6.66(q,J＝8.0Hz,2H),4.30-4.06(m,3H),3.37(s,1H),2.54(d,J＝4.0Hz,1H),1.16(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.8,168.6,151.2,141.7,136.2,134.6,133.4,132.6,131.0,130.9,130.0,129.6,129.1,127.5,123.8,123.6,121.9,121.0,120.6,116.3,94.4,83.6,62.5,42.3,13.8,onecarbon missing in the aliphatic region.IR(KBr)ν3425,2975,1718,1244,1026,754cm-1.HRMS(ESI)calcd for C26H21BrNO4[M+H]+490.0649,found 490.0653.
化合物3o(白色固体，79％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.74(d,J＝8.0Hz,1H),7.62(t,J＝8.0Hz,3H),7.46(d,J＝8.0Hz,1H),7.42-7.36(m,2H),7.26(d,J＝4.0Hz,1H),6.99(dd,J1＝J2＝8.0Hz,2H),6.76(d,J＝8.0Hz,1H),6.64(t,J＝8.0Hz,1H),4.35-4.31(m,1H),4.19-4.15(m,2H),2.68(d,J＝12.0Hz,1H),2.59(dd,J1＝J2＝4.0Hz,1H),2.39(s,3H),1.24(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.5,151.7,141.7,138.8,137.3,133.3,132.9,129.9,129.5,129.2,129.0,128.2,126.6,123.8,123.6,123.3,121.9,120.9,116.5,93.2,84.1,62.5,43.5,42.8,21.2,13.9.IR(KBr)ν3423,2984,1720,1305,1239,751cm-1.HRMS(ESI)calcd for C27H24NO4[M+H]+426.1700,found 426.1697.
化合物3p(白色固体，96％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ8.39(s,1H),8.06-7.96(m,4H),7.78(d,J＝8.0Hz,1H),7.64-7.58(m,3H),7.48(d,J＝8.0Hz,1H),7.42(t,J＝8.0Hz,1H),7.05(t,J＝8.0Hz,1H),7.00(d,J＝8.0Hz,1H),6.83(d,J＝8.0Hz,1H),6.67(t,J＝8.0Hz,1H),4.40-4.32(m,1H),4.24-4.17(m,2H),2.80-2.71(m,2H),1.26(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.6,151.7,141.8,136.3,133.4,133.0,132.9,132.5,130.0,129.6,129.0,128.3,128.0,127.6,126.6(2C),125.2,124.1,123.9,123.7,122.0,121.0,116.6,93.3,84.2,62.6,43.4,42.9,14.0.IR(KBr)ν3429,2984,1721,1280,1028,751cm-1.HRMS(ESI)calcd for C30H24NO4[M+H]+462.1700,found 462.1693.
化合物3q(白色固体，75％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ8.35(d,J＝8.0Hz,1H),8.27(d,J＝8.0Hz,1H),8.04(t,J＝8.0Hz,2H),7.78(d,J＝4.0Hz,1H),7.67-7.51(m,5H),7.44(t,J＝8.0Hz,1H),7.08(d,J＝8.0Hz,1H),7.02(t,J＝8.0Hz,1H),6.71(dd,J1＝8.0Hz,J2＝4.0Hz,2H),4.31-4.23(m,2H),4.16-4.08(m,1H),3.35(s,1H),2.57(dd,J1＝J2＝4.0Hz,1H),1.17(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.4,168.9,151.9,142.2,134.5,133.8,133.5,133.4,130.5,130.4,130.3,129.6,129.4,129.3,127.2,126.8,126.2,126.1,125.5,124.3,124.1,122.7,121.6,117.0,95.9,84.0,62.9,43.2,41.7,14.3.IR(KBr)ν3424,2987,1720,1239,1021,770cm-1.HRMS(ESI)calcd for C30H24NO4[M+H]+462.1700,found 462.1701.
化合物3r(白色固体，68％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.79(s,1H),7.73(d,J＝12.0Hz,1H),7.62(t,J＝8.0Hz,1H),7.49(d,J＝12.0Hz,1H),7.41(t,J＝8.0Hz,1H),6.99(q,J＝8.0Hz,2H),6.79(s,1H),6.70(d,J＝12.0Hz,1H),6.64(t,J＝8.0Hz,2H),4.31-4.10(m,3H),2.78(s,2H),1.17(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.6,168.6,151.2,150.2,143.3,141.6,133.4,132.6,129.9,129.6,129.0,123.9,123.6,121.8,121.1,116.3,110.8,109.5,88.3,83.9,62.3,42.1,40.4,13.8.IR(KBr)ν3432,1723,1240,1035,746cm-1.HRMS(ESI)calcd for C24H20NO5[M+H]+402.1336,found 402.1342.
化合物3s(白色固体，80％收率，通过柱色谱分离纯化(石油醚：乙酸乙酯＝3:1))：1H NMR(400MHz,DMSO-d6),δ7.66(d,J＝8.0Hz,1H),7.56(d,J＝8.0Hz,1H),7.43(d,J＝8.0Hz,1H),7.36(t,J＝8.0Hz,1H),6.92(q,J＝8.0Hz,2H),6.59(dd,J1＝J2＝12.0Hz,2H),4.27-4.11(m,2H),4.01(s,1H),2.54(d,J＝4.0Hz,1H),2.39(d,J＝16.0Hz,1H),1.99(s,3H),1.19(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.0,169.1,151.7,141.7,133.2,133.0,129.7,129.4,128.7,123.6(2C),121.9,120.5,116.0,90.9,83.7,62.2,42.3,40.3,23.5,13.9.IR(KBr)ν 3418,2990,1720,1306,1231,738cm-1.HRMS(ESI)calcd forC21H20NO4[M+H]+350.1387,found 350.1385.
化合物3t(白色固体，98％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.80(dd,J1＝J2＝12.0Hz,3H),7.64(t,J＝8.0Hz,1H),7.52-7.42(m,5H),7.01(dd,J1＝J2＝4.0Hz,1H),6.86-6.75(m,2H),4.37-4.27(m,1H),4.21-413(m,2H),2.73(d,J＝20.0Hz,1H),2.61(dd,J1＝J2＝4.0Hz,1H),1.22(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.9,168.5,156.1(d,J＝315.0Hz,1C),148.0(d,J＝20.0Hz,1C),141.6,138.6,133.4,132.8,130.1,128.7,128.3,126.2,123.8(d,J＝8.0Hz,1C),123.5(d,J＝11.0Hz,1C),117.8(d,J＝11.0Hz,1C),116.1,115.7,115.5,93.3,84.0,62.6,43.0,42.5,13.9.IR(KBr)ν3427,3060,1721,1487,1234,749cm-1.HRMS(ESI)calcd for C26H21FNO4[M+H]+430.1449,found 430.1455.
化合物3u(白色固体，84％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.81(t,J＝8.0Hz,3H),7.67(t,J＝8.0Hz,1H),7.50-7.43(m,5H),7.21(d,J＝4.0Hz,1H),7.03(dd,J1＝J2＝4.0Hz,1H),6.79(d,J＝4.0Hz,1H),4.37-4.12(m,3H),2.73(d,J＝20.0Hz,1H),2.63(dd,J1＝J2＝4.0Hz,1H),1.22(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.7,168.4,150.7,141.5,138.3,133.4,132.7,130.1,129.0,128.7(2C),128.2,126.1,124.6,124.0,123.9,123.8,118.2,93.4,83.9,62.5,42.9,42.4,13.9.IR(KBr)ν3431,2988,1723,1240,1021,756cm-1.HRMS(ESI)calcd for C26H21ClNO4[M+H]+446.1154,found 446.1153.
化合物3v(白色固体，88％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.81(t,J＝8.0Hz,3H),7.68(t,J＝8.0Hz,1H),7.48(d,J＝8.0Hz,5H),7.33(s,1H),7.15(d,J＝12.0Hz,1H),6.74(d,J＝12.0Hz,1H),4.34-4.15(m,3H),2.68(q,J＝16.0Hz,2H),1.23(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ169.7,168.4,151.1,141.5,138.3,133.4,132.7,131.9,131.6,130.1,128.7,128.2,126.1,124.5,123.9,123.8,118.7,112.4,93.4,83.9,62.5,42.9,42.3,13.9.IR(KBr)ν3428,3065,2984,1725,1237,754cm- 1.HRMS(ESI)calcd for C26H21BrNO4[M+H]+490.0649,found 490.0650.
化合物3w(白色固体，80％收率，通过过滤分离纯化)：1H NMR(400MHz,DMSO-d6),δ7.83(t,J＝8.0Hz,2H),7.74(d,J＝8.0Hz,1H),7.64(t,J＝8.0Hz,1H),7.52-7.40(m,5H),6.81(t,J＝8.0Hz,2H),6.65(d,J＝8.0Hz,1H),4.34-4.09(m,3H),2.66(d,J＝16.0Hz,1H),2.59(dd,J1＝J2＝4.0Hz,1H),2.00(s,3H),1.24(t,J＝8.0Hz,3H)；13C NMR(100MHz,DMSO-d6)δ170.1,168.5,149.5,141.7,138.9,133.3,133.0,130.0,129.8,129.6,129.5,128.6,128.3,126.2,123.8,123.7,121.6,116.2,93.2,84.1,62.5,43.6,42.8,20.0,13.9.IR(KBr)ν3431,3057,2986,1723,1311,1239,749cm-1.HRMS(ESI)calcd for C27H24NO4[M+H]+426.1700,found 426.1702.
以上显示和描述了本发明的基本原理和主要特征以及本发明的优点。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下，本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
Claims (10)
1.一种色满桥环异吲哚酮，其结构式如下：
，
其中，R1为烷基；R2为芳基或烷基；R3为H、卤原子或烷基。
2.根据权利要求1所述的色满桥环异吲哚酮的制备方法，其特征在于：将异吲哚酮和邻羟基查尔酮，在有机溶剂中，酸的存在下，25-100 oC反应6-72 h，薄层色谱跟踪反应至完全，反应结束后，通过过滤或者柱色谱分离纯化，得目标产物，其反应通式如下：
其中，R1为烷基；R2为芳基或烷基；R3为H、卤原子或烷基。
3.根据权利要求2所述的色满桥环异吲哚酮的制备方法，其特征在于：所述的酸为Lewis酸或质子酸。
4.根据权利要求3所述的色满桥环异吲哚酮的制备方法，其特征在于：所述Lewis酸为三氟甲磺酸铜、三氟甲磺酸锌、三氟甲磺酸钇、三氟甲磺酸铟、三氟甲磺酸铋、三氟甲磺酸钪、三氟甲磺酸铁、三氯化铁或溴化铜；质子酸为三氟甲磺酸、三氟醋酸、甲磺酸、对甲苯磺酸、醋酸或硫酸。
5.根据权利要求2所述的色满桥环异吲哚酮的制备方法，其特征在于：所述的酸的物质的量为邻羟基查尔酮物质的量的20%。
6.根据权利要求2所述的色满桥环异吲哚酮的制备方法，其特征在于：所述的有机溶剂为乙腈、甲苯、甲醇、氯仿、二氯甲烷、1,2-二氯乙烷、四氢呋喃、1,4-二氧六环或乙酸乙酯。
7.根据权利要求6所述的色满桥环异吲哚酮的制备方法，其特征在于：所述的有机溶剂为乙腈。
8.根据权利要求2所述的色满桥环异吲哚酮的制备方法，其特征在于：所述反应温度为35 ℃。
9.根据权利要求2所述的色满桥环异吲哚酮的制备方法，其特征在于：所述异吲哚酮与邻羟基查尔酮的摩尔比为1:1 -2:1。
10.根据权利要求9所述的色满桥环异吲哚酮的制备方法，其特征在于：所述异吲哚酮与邻羟基查尔酮的摩尔比为1.1:1。
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