CN109134875B - Preparation of chiral covalent organic framework material with L-menthol as chiral source - Google Patents
Preparation of chiral covalent organic framework material with L-menthol as chiral source Download PDFInfo
- Publication number
- CN109134875B CN109134875B CN201810979725.8A CN201810979725A CN109134875B CN 109134875 B CN109134875 B CN 109134875B CN 201810979725 A CN201810979725 A CN 201810979725A CN 109134875 B CN109134875 B CN 109134875B
- Authority
- CN
- China
- Prior art keywords
- chiral
- menthol
- hours
- crude product
- organic framework
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 title claims abstract description 17
- 239000013310 covalent-organic framework Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000463 material Substances 0.000 title abstract description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012043 crude product Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 claims abstract description 4
- SQQKOTVDGCJJKI-UHFFFAOYSA-N 2,5-dibromobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1Br SQQKOTVDGCJJKI-UHFFFAOYSA-N 0.000 claims abstract description 4
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002390 rotary evaporation Methods 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- VVTLQYQLVFNQBM-UHFFFAOYSA-N 2-[3,5-bis(2-trimethylsilylethynyl)phenyl]ethynyl-trimethylsilane Chemical compound C[Si](C)(C)C#CC1=CC(C#C[Si](C)(C)C)=CC(C#C[Si](C)(C)C)=C1 VVTLQYQLVFNQBM-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 4
- KVFXLCABRSQDFB-UHFFFAOYSA-N 2,5-dibromobenzoyl chloride Chemical compound ClC(=O)C1=CC(Br)=CC=C1Br KVFXLCABRSQDFB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000007039 two-step reaction Methods 0.000 abstract 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of a chiral covalent organic framework by taking L-menthol as a chiral source, which comprises the following steps: taking thionyl chloride, 2, 5-dibromobenzoic acid and L-menthol as raw materials and toluene as a solvent, and synthesizing a white crystal A through two-step organic synthesis reaction; with 1,3, 5-tribromobenzene, Pd (PPh)3)2Cl2、CuI、PPh3And trimethylsilylacetylene as raw materials, and synthesizing a compound B through two-step reaction; a, B, Pd (PPh)3)2Cl2、PPh3And adding CuI into a three-necked bottle, injecting triethylamine, reacting at 90 ℃ for 18 hours, and purifying a crude product to obtain a brown solid which is a chiral covalent organic framework material. The covalent organic framework material which takes the L-menthol as the chiral source and is obtained by the invention has unique chiral structure and tubular shape and can be used as a chiral resolution material.
Description
Technical Field
The invention belongs to the field of high polymer materials and engineering, and particularly relates to a preparation method of a chiral covalent organic framework with L-menthol as a chiral source.
Background
Chiral resolution is significant, and isomers with different optical rotation usually have obvious difference in properties. However, natural chiral substances are not common in nature, and the existing technology and the traditional process means are easy to cause serious pollution to the environment, so that the preparation of a novel porous material for chiral resolution has important scientific significance and research value.
Disclosure of Invention
The invention aims to provide a preparation method of a covalent organic framework by taking L-menthol as a chiral source, which contains a chiral structure, has a unique appearance structure of a tubular shape, can be used for chiral resolution, and has a great development prospect.
The purpose of the invention is realized by the following technical scheme: a method for preparing a covalent organic framework with L-menthol as a chiral source comprises the following steps:
(1) under the protection of nitrogen, thionyl chloride (13.5 mL) is injected into a three-necked flask filled with 2, 5-dibromobenzoic acid (3.00 g, 9.26 mmol), heated to 75 ℃ by an oil bath, stirred and reacted for 4 hours, and the compound is 2, 5-dibenzoyl chloride obtained by rotary evaporation;
(2) under the protection of nitrogen, L-menthol (2.89 g, 18.5 mmol) is injected into a three-neck flask containing 2, 5-dibromobenzoyl chloride (1.69 g, 8.33 mmol), toluene (15.0 mL) is used as a solvent, the reaction is carried out for 16 hours at 110 ℃, and the crude product which is removed of toluene by rotary evaporation is purified by a silica gel chromatographic column (R)f=0.44, eluent is: n-hexane/ethyl acetate =20: 1), rotary evaporation to obtain white crystals a;
(3) 1,3, 5-tribromobenzene (5.00g, 15.9mmol), Pd (PPh3)2Cl2(340mg, 0.490mmol), CuI (90.0mg, 0.490mmol), PPh3(129mg, 0.490mmol) were put in a three-necked flask, nitrogen protected, 176mL of triethylamine was added as a solvent, after 15 minutes of reaction, 9.00mL of trimethylsilylacetylene was added, reaction was carried out at 90 ℃ for 16 hours, and the crude product was purified by silica gel chromatography (R)f=0.42, eluent is n-hexane), rotary evaporation is carried out to obtain light yellow concentrated solution, crystal precipitation is carried out after cooling, and the compound 1,3, 5-tri (trimethylsilylethynyl) benzene is obtained;
(4) 1,3, 5-tris (trimethylsilylethynyl) benzene (1.00g, 2.73mmol) and K2CO3(57.0mg, 0.410mmol) were charged into a three-necked flask and protected with nitrogen. Then adding 14.4mL tetrahydrofuran and 4.30mL methanol, stirring at room temperature for 6 hours, filtering, rotary evaporating to remove tetrahydrofuran and methanol solvent, purifying the crude product by silica gel chromatography (R)f=0.56, eluent is: n-hexane) to obtain a yellow solid B after rotary evaporation;
(5) a (600 mg, 1.00 mmol), B (94.7 mg, 0.631 mmol), Pd (PPh3)2Cl2 (65.1 mg, 0.0940 mmol), PPh3(114mg,0.438mmol), and CuI (68.1 mg, 0.371 mmol) were charged into a three-necked flask, 50.0mL of triethylamine was injected under nitrogen gas protection, and reacted at 90 ℃ for 18 hours to obtain a crude product, which was then washed with methanol, a KI aqueous solution, and chloroform, respectively, and dried to obtain a brown solid.
The invention has the beneficial effects that: the covalent organic framework taking the L-menthol as the chiral source can be used for chiral resolution of raceme, so that the chiral resolution efficiency is high and the energy consumption is low.
Drawings
FIG. 1 is an infrared spectrum of a covalent organic framework with L-menthol as a chiral source.
3448cm-1(characteristic peaks due to hydrogen bonding); 2951cm-1(CH3Stretching vibration of (2); 2202cm in length-1(stretching vibration of C.ident.C); 1725cm-1(C = O stretching vibration of ester group); 1583cm-1(double bond stretching vibration of aromatic ring); 1233cm-1(C-O stretching vibration of ester group); 547cm-1(stretching vibration of C-Br).
FIG. 2 scanning electron micrograph of covalent organic framework with L-menthol as chiral source.
From the SEM image, it can be observed that the chiral covalent organic skeleton is in a polygonal and smooth-surface tubular shape, because the polymer is a conjugated polymer and the benzene ring generates strong pi-pi superposition, the polymer has good crystallization effect and forms a special tubular shape.
Detailed Description
In order that the objects and advantages of the invention will be more clearly understood, the invention is further described in detail below with reference to examples. It should be understood that the specific examples described herein are intended to be illustrative only and are not intended to be limiting.
The invention is implemented as follows: a preparation method of a chiral covalent organic framework with L-menthol as a chiral source comprises the following steps:
(1) under the protection of nitrogen, thionyl chloride (13.5 mL) is injected into a three-necked flask filled with 2, 5-dibromobenzoic acid (3.00 g, 9.26 mmol), heated to 75 ℃ by an oil bath, stirred and reacted for 4 hours, and the compound is 2, 5-dibenzoyl chloride obtained by rotary evaporation;
(2) under the protection of nitrogen, L-menthol (2.89 g, 18.5 mmol) is injected into a three-neck flask containing 2, 5-dibromobenzoyl chloride (1.69 g, 8.33 mmol), toluene (15.0 mL) is used as a solvent, the reaction is carried out for 16 hours at 110 ℃, and the crude product which is removed of toluene by rotary evaporation is purified by a silica gel chromatographic column (R)f=0.44, eluent is: n-hexane/ethyl acetate =20: 1), and rotary evaporation is carried out to obtain white crystals a;
(3) 1,3, 5-tribromobenzene (5.00g, 15.9mmol), Pd (PPh3)2Cl2(340mg, 0.490mmol), CuI (90.0mg, 0.490mmol), PPh3(129mg, 0.490mmol) were charged into a three-necked flask, nitrogen-protected, 176mL of triethylamine was added as a solvent, and after 15 minutes of reaction, 9.00mL of trimethylsilylacetylene was added and reacted at 90 ℃ for 16 hours. The crude product is purified by chromatography on a silica gel column (R)f=0.42, eluent is n-hexane), rotary evaporation is carried out to obtain light yellow concentrated solution, crystal precipitation is carried out after cooling, and the compound 1,3, 5-tri (trimethylsilylethynyl) benzene is obtained;
(4) 1,3, 5-tris (trimethylsilylethynyl) benzene (1.00g, 2.73mmol) and K2CO3(57.0mg, 0.410mmol) were charged into a three-necked flask and protected with nitrogen. Then, 14.4mL of tetrahydrofuran and 4.30mL of methanol were added, and the mixture was stirred at room temperature for 6 hours. Filtering, rotary evaporating to remove tetrahydrofuran and methanol solvent, and purifying the crude product with silica gel chromatographic column (R)fThe lotion =0.56 was: n-hexane) to obtain a yellow solid B after rotary evaporation;
(5) a (600 mg, 1.00 mmol), B (94.7 mg, 0.631 mmol), Pd (PPh3)2Cl2 (65.1 mg, 0.0940 mmol), PPh3(114mg,0.438mmol), and CuI (68.1 mg, 0.371 mmol) were charged into a three-necked flask, 50.0mL of triethylamine was injected under nitrogen gas protection, and reacted at 90 ℃ for 18 hours to obtain a crude product, which was then washed with methanol, a KI aqueous solution, and chloroform, respectively, and dried to obtain a brown solid.
The novel chiral covalent organic framework which takes the L-menthol as the chiral source and is obtained by the specific implementation contains a chiral structure and a unique tubular shape and can be used as a novel material for chiral resolution.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that those skilled in the art can make various improvements and modifications without departing from the principle of the present invention, and these improvements and modifications should also be construed as the protection scope of the present invention.
Claims (1)
1. The preparation method of the chiral covalent organic framework with L-menthol as a chiral source is characterized by comprising the following steps:
(1) under the protection of nitrogen, 13.5mL of thionyl chloride is injected into a three-necked bottle containing 3.00g of 2, 5-dibromobenzoic acid, heated to 75 ℃ by oil bath, stirred and reacted for 4 hours, and then the compound is 2, 5-dibenzoyl chloride after rotary evaporation;
(2) under the protection of nitrogen, 2.89g of L-menthol is injected into a three-necked flask containing 1.69g of 2, 5-dibromobenzoyl chloride, 15mL of toluene is used as a solvent, the reaction is carried out for 16 hours at 110 ℃, and the crude product which is subjected to rotary evaporation to remove the toluene is subjected to RfPurifying by silica gel chromatographic column with eluent of n-hexane/ethyl acetate of 20:1, and performing rotary evaporation to obtain white crystal A;
(3) putting 5.00g of 1,3, 5-tribromobenzene, Pd (PPh3)2Cl 2340 mg, CuI 90.0mg and PPh 3129 mg into a three-neck flask, performing nitrogen protection, adding 176mL of triethylamine as a solvent, reacting for 15 minutes, adding 9.00mL of trimethylsilylacetylene, reacting at 90 ℃ for 16 hours, and subjecting the crude product to R reactionfPurifying with silica gel chromatographic column (0.42) and eluting agent n-hexane, rotary evaporating to obtain light yellow concentrated solution, cooling to obtain crystal, and separating to obtain 1,3, 5-tri (trimethylsilylethynyl) benzene;
(4) adding 1.00g of 1,3, 5-tri (trimethylsilylethynyl) benzene and K2CO357.0mg into a three-neck bottle, performing nitrogen protection, adding 14.4mL of tetrahydrofuran and 4.30mL of methanol, stirring at room temperature for 6 hours, filtering, performing rotary evaporation to remove tetrahydrofuran and methanol solvent, and subjecting the crude product to R treatmentfPurifying with silica gel chromatographic column (0.56) and eluting with n-hexane, and rotary evaporating to obtain yellow solid B;
(5) 600mg of A, 94.7mg of B, 2 Cl265.1mg of Pd (PPh3), 3114-3114 mg and 68.1mg of CuI are put into a three-necked flask, 50.0mL of triethylamine is injected under the protection of nitrogen gas, and the mixture reacts at 90 ℃ for 18 hours to obtain a crude product, and then the crude product is washed by methanol, a KI aqueous solution and chloroform respectively and dried to obtain a brown solid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810979725.8A CN109134875B (en) | 2018-08-27 | 2018-08-27 | Preparation of chiral covalent organic framework material with L-menthol as chiral source |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810979725.8A CN109134875B (en) | 2018-08-27 | 2018-08-27 | Preparation of chiral covalent organic framework material with L-menthol as chiral source |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109134875A CN109134875A (en) | 2019-01-04 |
| CN109134875B true CN109134875B (en) | 2021-08-31 |
Family
ID=64828144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810979725.8A Expired - Fee Related CN109134875B (en) | 2018-08-27 | 2018-08-27 | Preparation of chiral covalent organic framework material with L-menthol as chiral source |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109134875B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111540620B (en) * | 2020-01-08 | 2022-03-18 | 中南民族大学 | Super capacitor with covalent organic framework composite film and preparation method thereof |
| CN111545249B (en) * | 2020-04-27 | 2023-03-21 | 齐齐哈尔大学 | Preparation method of conjugated microporous polymer/palladium-nickel bimetallic catalyst |
| CN111617646B (en) * | 2020-05-11 | 2022-03-04 | 齐齐哈尔大学 | Preparation method of chiral conjugated microporous polymer/silicon dioxide composite membrane |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011236143A (en) * | 2010-05-10 | 2011-11-24 | Saitama Univ | Liquid crystalline pyrene derivative, organic semiconductor, and organic semiconductor element |
| CN105622579A (en) * | 2015-12-29 | 2016-06-01 | 兰州大学 | Chirality covalent organic framework and synthesis method and application thereof |
| CN106311334A (en) * | 2015-07-02 | 2017-01-11 | 中国科学院大连化学物理研究所 | Metallic cobalt complexed polymer catalyst and preparation method and application thereof |
-
2018
- 2018-08-27 CN CN201810979725.8A patent/CN109134875B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011236143A (en) * | 2010-05-10 | 2011-11-24 | Saitama Univ | Liquid crystalline pyrene derivative, organic semiconductor, and organic semiconductor element |
| CN106311334A (en) * | 2015-07-02 | 2017-01-11 | 中国科学院大连化学物理研究所 | Metallic cobalt complexed polymer catalyst and preparation method and application thereof |
| CN105622579A (en) * | 2015-12-29 | 2016-06-01 | 兰州大学 | Chirality covalent organic framework and synthesis method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| Asymmetric sulfoxidation of prochiral sulfides using aminoalcohol derived chiral C3-symmetric trinuclear vanadium Schiff base complexes;Paulsamy Suresh, et al;《Tetrahedron: Asymmetry》;20071126;第18卷(第23期);第2820-2827页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109134875A (en) | 2019-01-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Buechi et al. | Nitro olefination of indoles and some substituted benzenes with 1-dimethylamino-2-nitroethylene | |
| CN109134875B (en) | Preparation of chiral covalent organic framework material with L-menthol as chiral source | |
| CN114349674B (en) | Thiourea compound and preparation method thereof | |
| Büchi et al. | Photochemical reactions. XI. diphenylacetylene1-3 | |
| CN116283899A (en) | 3-perfluoroalkyl benzothiophene [ b ] cyclopentenone compound and synthesis method thereof | |
| CN108976249B (en) | Preparation method of cycloindene corrole-fullerene star-shaped compound | |
| CN113061104B (en) | Synthetic method of alkyl thioether compound | |
| CN104016867A (en) | Synthesis method of 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-binitro-3,4:9,10-perylene tetracarboxylate | |
| Garratt et al. | Stereoselective control in the alkylation and annelation of anions and dianions derived from 5-norbornene-2, 3-dicarboximides | |
| CN110845512B (en) | Total synthesis method of triterpenoid natural product (+) -Arisugacins F/G | |
| CN115197232A (en) | Cyclopropane fused oxygen bridge hexacyclic compound and synthesis method thereof | |
| Ito | The rapid synthesis of π-extended azacorannulenes | |
| Wang et al. | Novel highly fluorescent dendritic chiral amines: synthesis and optical properties | |
| CN107445835B (en) | Synthesis method of 1, 2-dihydro cyclobuteno [ a ] naphthalene derivative and precursor thereof | |
| CN115626895B (en) | Biaryl bridged eight-membered or nine-membered or ten-membered nitrogen-containing heterocyclic compound and synthesis method thereof | |
| Voronkov et al. | Regio-and diastereoselective synthesis of bifunctionalized limonenes | |
| Khakina et al. | The Remarkable Chemistry of Trannulenes: Green Fluorinated Fullerenes with Unconventional Aromaticity | |
| CN111233616A (en) | Pyrenyl [4] helicene and synthesis method and application thereof | |
| CN111362795A (en) | Preparation method of substituted butyrate derivatives | |
| CN115716816B (en) | Method for preparing bromothiophene derivative | |
| Niu et al. | Synthesis of 5′‐Functionalized Indolinospiropyrans with Vinylene Unit as Linker | |
| CN106831528B (en) | Synthetic method of pyrrole-3-formate compound | |
| CN103508999A (en) | Maxacalcitol synthesizing intermediate and preparation method and application thereof | |
| CN114262290B (en) | 4-methylene pyrrolidine-2-thioketone compound, and synthetic method and application thereof | |
| CN108101906B (en) | Preparation method of cyclopentyl [ f ] pyrrolo [2,1,5-cd ] indolizine derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210831 |