CN112707938A - Tetra-substituted bifluorenyliron compound and preparation method thereof - Google Patents
Tetra-substituted bifluorenyliron compound and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- -1 2, 7-disubstituted fluorene Chemical class 0.000 claims abstract description 13
- 229960002089 ferrous chloride Drugs 0.000 claims abstract description 9
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims abstract description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 3
- 125000005011 alkyl ether group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 150000008379 phenol ethers Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229960001701 chloroform Drugs 0.000 claims 1
- 230000021615 conjugation Effects 0.000 abstract description 4
- 230000031700 light absorption Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000002506 iron compounds Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 25
- 229910052742 iron Inorganic materials 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 238000002484 cyclic voltammetry Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- KRPHZIRPXLJJIZ-UHFFFAOYSA-N 2,7-dimethyl-9h-fluorene Chemical compound CC1=CC=C2C3=CC=C(C)C=C3CC2=C1 KRPHZIRPXLJJIZ-UHFFFAOYSA-N 0.000 description 1
- IHZCVUBSTYOFSJ-UHFFFAOYSA-N 2,7-dinitro-9h-fluorene Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C([N+](=O)[O-])C=C3CC2=C1 IHZCVUBSTYOFSJ-UHFFFAOYSA-N 0.000 description 1
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-UHFFFAOYSA-N 0.000 description 1
- IIYYRXVPODDRJO-UHFFFAOYSA-N 9h-fluorene-2,7-diol Chemical compound OC1=CC=C2C3=CC=C(O)C=C3CC2=C1 IIYYRXVPODDRJO-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of organic synthesis, and particularly discloses a tetra-substituted bifluorenyliron compound and a preparation method thereof, wherein the tetra-substituted bifluorenyliron compound is specifically 2,2 ', 7, 7' -tetra-substituted bifluorenyliron, and the tetra-substituent is the same group of nitro, alkyl, aryl, aldehyde group, phenol ether group, alkyl ether group, amino and hydroxyl. The preparation method comprises the following steps: firstly, adding 2, 7-disubstituted fluorene, an alkaline catalyst and anhydrous tetrahydrofuran into a reaction container, fully stirring, and reacting for at least 15-45min in an air atmosphere under ice bath; slowly adding ferrous chloride, and continuously reacting for 4-8h at room temperature; and finally, extracting and purifying by using an organic solvent. The 2,2 ', 7, 7' -tetra-substituted bifluorene iron compound provided by the invention has diversity in structure and function, and simultaneously has higher space symmetry and conjugation, so that the compound has good electrical property and ultraviolet light absorption property.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a tetra-substituted bifluorenyliron compound and a preparation method thereof.
Background
The ferrocene compound is an important organic compound and has wide application in industries such as industry, agriculture, medicine, aerospace, energy conservation, environmental protection and the like. The ferrocene molecules have polarity, and iron atoms coordinate with two cyclopentadiene to form a sandwich structure with stable space. The ferrocene compound has high thermal stability, can not be decomposed within 400 ℃, also has high chemical stability, and is stable under the conditions of strong acid-base property, oxidation and hydrogenation. In addition, ferrocene compounds have high radiation resistance and are often used as ultraviolet absorbers. However, the traditional ferrocene compound has few substituted sites, is a mono-substituted compound in general, and has few di-substituted and more ferrocene compounds, so the structural diversity and the functional diversity of the ferrocene compound are greatly limited.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a tetra-substituted bifluorenyliron compound and a preparation method thereof.
The technical scheme of the invention is as follows:
a tetra-substituted bifluorenyliron compound has a structural formula as follows:
wherein R is1、R2、R1′、R2' is the same group of nitryl, alkyl, aryl, aldehyde group, phenol ether group, alkyl ether group, amido group and hydroxyl group.
The preparation method of the tetra-substituted bifluorenyliron compound comprises the following operation steps:
(1) adding 2, 7-disubstituted fluorene, an alkaline catalyst and anhydrous tetrahydrofuran into a dry reaction container, fully stirring, and reacting in an air atmosphere for at least 15-45min under ice bath;
(2) slowly adding ferrous chloride into the mixed system in the step (1), and continuously reacting for 4-8h at room temperature;
(3) and (3) extracting and purifying the product obtained in the step (2) by using an organic solvent.
Preferably, the following components are added in the amount of each 40-100ml of anhydrous tetrahydrofuran: 0.5-3mmol of 2, 7-disubstituted fluorene, 3-8mmol of alkaline catalyst and 0.5-6mmol of ferrous chloride.
Further preferably, the basic catalyst is any one or more of sodium hydride, potassium hydride, lithium aluminum hydride, n-butyllithium, and t-butyllithium.
More preferably, the organic solvent is any one or more of petroleum ether, dichloromethane, chloroform, ethyl acetate, benzene and its homologues.
Compared with the prior art, the 2,2 ', 7, 7' -tetrasubstituted bifluorenyliron synthesized by the method can be modified on a double-layer bifluorenyliron ring, so that a bifluorenyliron double-layer structure has four same or different substituent groups, and the bifluorenyliron compound has diversity in structure and function; because the 2,2 ', 7, 7' -tetra-substituted bifluorene iron has higher space symmetry and conjugation, the substitute has good electrical property and stronger ultraviolet light absorption property.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a general reaction formula for preparing tetra-substituted bifluorenyliron compounds according to the present invention;
FIG. 2 is a plot of cyclic voltammetry for the product 2,2 ', 7, 7' -tetranitrobifluoreneiron of example 1;
FIG. 3 is a graph showing the ultraviolet absorption spectrum of 2,2 ', 7, 7' -tetranitrobifluoreneiron product of example 1;
FIG. 4 is a plot of cyclic voltammetry for the product 2,2 ', 7, 7' -tetraaminobifluoreneiron of example 2;
FIG. 5 is a graph showing an ultraviolet absorption spectrum of 2,2 ', 7, 7' -tetraaminobifluoreneiron which is a product of example 2;
FIG. 6 is a plot of cyclic voltammetry for the product 2,2 ', 7, 7' -tetramethylbifluoreneiron of example 3;
FIG. 7 is a graph showing an ultraviolet absorption spectrum of 2,2 ', 7, 7' -tetramethylbifluoreneiron which is a product of example 3;
FIG. 8 is a plot of cyclic voltammetry for the product 2,2 ', 7, 7' -tetrahydroxybifluoreneiron of example 4;
FIG. 9 is a UV absorption spectrum of 2,2 ', 7, 7' -tetrahydroxybifluoreneiron product of example 4.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
1mmol of 2, 7-dinitrofluorene, 5mmol of sodium hydride and 80ml of tetrahydrofuran are respectively added into a reaction bottle, stirred for 30 minutes in ice bath, then added with 2mmol of ferrous chloride, and stirred for reaction for 6 hours at room temperature. Then, water quenching reaction is added, and the resultant is extracted by ethyl acetate in a separating funnel and dried in vacuum to obtain orange red 2,2 ', 7, 7' -tetranitrobifluorene iron.
Example 2
1.1mmol of 2, 7-diaminofluorene, 5.2mmol of lithium aluminum hydride and 85ml of tetrahydrofuran are respectively added into a reaction bottle, stirred for 15 minutes in ice bath, added with 2.2mmol of ferrous chloride and continuously stirred for reaction for 5 hours at room temperature. And then adding water to quench the reaction, extracting the product by using petroleum ether in a separating funnel, and drying the product in vacuum to obtain orange-red 2,2 ', 7, 7' -tetraamino-bifluorene iron.
Example 3
Respectively adding 0.5mmol of 2, 7-dimethylfluorene, 8mmol of n-butyllithium and 40ml of tetrahydrofuran into a reaction bottle, stirring for 45 minutes in an ice bath, then adding 0.5mmol of ferrous chloride, and continuously stirring for reaction for 4 hours at room temperature. Then, water quenching reaction was added, and the resultant was extracted with dichloromethane in a separatory funnel and dried under vacuum to obtain orange-red 2,2 ', 7, 7' -tetramethylbifluoreneiron.
Example 4
Respectively adding 3mmol of 2, 7-dihydroxyfluorene, 3mmol of tert-butyllithium and 100ml of tetrahydrofuran into a reaction bottle, stirring for 50 minutes in ice bath, then adding 6mmol of ferrous chloride, and continuously stirring for reaction for 8 hours at room temperature. Then, water quenching reaction is added, and the resultant is extracted by benzene in a separating funnel and dried in vacuum to obtain orange red 2,2 ', 7, 7' -tetrahydroxy bifluorene iron.
And performing cyclic voltammetry on the product obtained in the above embodiment, wherein in the test, in a three-electrode system constructed by taking a glassy carbon electrode as a working electrode, Ag/AgCl as a reference electrode and a platinum wire electrode as an auxiliary electrode, an acetonitrile solution of 0.1mol/L tetrabutyl ammonium hexafluorophosphate is used as an electrolyte solution, and nitrogen is introduced to remove oxygen for 30min for the test. 2,2 ', 7, 7' -tetranitrobifluoreneiron of example 1, as shown in FIG. 2: the initial potential is 0V, the highest potential is 2V, the lowest potential is-0.5V, the scanning rate is 0.1V/s, the scanning range is-0.5V- +2V, when scanning from 0 to +2V, 2,2 ', 7, 7' -tetranitrobifluorene iron is oxidized, the oxidation potential is +1.6V, when scanning from +2V to-0.5V, the oxidation product is reduced back to 2,2 ', 7, 7' -tetranitrobifluorene iron, and the reduction potential is + 1.7V. 2,2 ', 7, 7' -tetraaminobifluoreneiron of example 2, as shown in FIG. 4: the initial potential of the cyclic voltammetry test is 0V, the highest potential is +1.75V, the lowest potential is-1.75V, the scanning rate is 0.1V/s, the scanning range is-1.75V to +1.75V, when scanning from 0 to +1.75V, 2,2 ', 7, 7' -tetraaminobifluorene iron is oxidized, the oxidation potential is +0.7V, and when scanning from +1.75 to-1.75V, the oxidation product is reduced back to 2,2 ', 7, 7' -tetraaminobifluorene iron, and the reduction potential is + 0.8V. 2,2 ', 7, 7' -tetramethylbifluorenyliron of example 3, as shown in FIG. 6: the initial potential of the cyclic voltammetry test is 0V, the highest potential is +1.75V, the lowest potential is-1.75V, the scanning rate is 0.1V/s, the scanning range is-1.75V to +1.75V, when scanning from 0 to +1.75V, 2,2 ', 7, 7' -tetramethyl bifluorene iron is oxidized, the oxidation potential is +0.5V, and when scanning from +1.75 to-1.75V, the oxidation product is reduced, and the reduction potential is + 0.6V. 2,2 ', 7, 7' -tetramethylbifluorenyliron of example 4, as shown in FIG. 8: the initial potential of the cyclic voltammetry test is 0V, the highest potential is +1.2V, the lowest potential is-1.2V, the scanning rate is 0.1V/s, the scanning range is-1.2V to +1.2V, when scanning from 0 to +1.2V, 2,2 ', 7, 7' -tetramethyl difluorene iron is oxidized, the oxidation potential is +0.75V, when scanning from +1.2V to-1.2V, the oxidation product is reduced to 2,2 ', 7, 7' -tetramethyl difluorene iron, and the reduction potential is + 0.8V. The 2,2 ', 7, 7' -tetra-substituted bifluorenyliron structure has good space symmetry and conjugation, and four representative compounds of the structure can be subjected to electrochemical oxidation reduction, so that the structure has good electrical properties.
The products of the above examples were tested for uv absorption by dissolving the product in ethyl acetate and testing in a 10mm thick quartz cuvette. 2,2 ', 7, 7' -tetranitrobifluoreneiron of example 1, with a light scanning range of 250nm to 450nm, FIG. 3 shows that it has strong absorption at 350 nm; 2,2 ', 7, 7' -tetraaminobifluorene iron of example 2, the light scanning range is 190nm to 500nm, and fig. 4 shows that it has strong absorption to light at 260nm and 325 nm; 2,2 ', 7, 7' -tetramethylbifluorenyliron of example 3, the light scanning range was 240nm to 450nm, and fig. 7 shows that it has strong absorption at 280nm and 350 nm; 2,2 ', 7, 7' -tetramethylbifluoreneiron of example 4, which had a light scanning range of 300nm to 450nm, was strongly absorbed at 340nm as shown in FIG. 9. The 2,2 ', 7, 7' -tetra-substituted bifluorenyliron structure has good space symmetry and conjugation, and an ultraviolet absorption test shows that the structure has high ultraviolet absorption capacity and can be used as a novel light absorption material.
The invention is not to be considered as limited to the particular embodiments shown and described, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (5)
1. A tetra-substituted bifluorenyliron compound is characterized in that: the structural formula is as follows:
wherein R is1、R2、R1′、R2' is the same group of nitro, alkyl, aromatic group, aldehyde group, phenol ether group, alkyl ether group, amido group and hydroxyl groupAnd (4) clustering.
2. The method for producing a tetra-substituted bifluorenyliron-based compound according to claim 1, wherein: the method comprises the following operation steps:
(1) adding 2, 7-disubstituted fluorene, an alkaline catalyst and anhydrous tetrahydrofuran into a dry reaction container, fully stirring, and reacting in an air atmosphere for at least 15-45min under ice bath;
(2) slowly adding ferrous chloride into the mixed system in the step (1), and continuously reacting for 4-8h at room temperature;
(3) and (3) extracting and purifying the product obtained in the step (2) by using an organic solvent.
3. The method for producing a tetra-substituted bifluorenyliron-based compound according to claim 2, characterized in that: the following components are added in each 40-100ml of anhydrous tetrahydrofuran: 0.5-3mmol of 2, 7-disubstituted fluorene, 3-8mmol of alkaline catalyst and 0.5-6mmol of ferrous chloride.
4. The method for producing a tetra-substituted bifluorenyliron-based compound according to claim 2, characterized in that: the alkaline catalyst is any one or more of sodium hydride, potassium hydride, lithium aluminum hydride, n-butyl lithium and tert-butyl lithium.
5. The method for producing a tetra-substituted bifluorenyliron-based compound according to claim 2, characterized in that: the organic solvent is one or more of petroleum ether, dichloromethane, trichloromethane, ethyl acetate, benzene and homologues of benzene.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1643002A (en) * | 2002-03-23 | 2005-07-20 | 赛拉尼斯温特斯股份有限公司 | Non-metallocene, its preparation method and use in olefin polymerization |
| CN1742028A (en) * | 2003-01-28 | 2006-03-01 | 托塔尔石油化学产品研究弗吕公司 | Group III bridged ionic metallocene based on cyclopentadienyl-fluorenyl ligands |
| CN102083844A (en) * | 2008-06-02 | 2011-06-01 | 尤米科尔股份公司及两合公司 | Process for preparing dienyl-ruthenium complexes |
| CN102964390A (en) * | 2012-11-27 | 2013-03-13 | 中国科学院上海有机化学研究所 | Planar chiral ferrocene compound and synthetic method and application thereof |
| CN105254682A (en) * | 2015-11-10 | 2016-01-20 | 中国科学院上海有机化学研究所 | Planar chiral ferrocene compound, synthetic method and application |
| CN109721630A (en) * | 2017-10-31 | 2019-05-07 | 上海茂晟康慧科技有限公司 | A kind of synthetic method of Ugi ' s amine and its derivative |
-
2021
- 2021-01-06 CN CN202110014188.5A patent/CN112707938A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1643002A (en) * | 2002-03-23 | 2005-07-20 | 赛拉尼斯温特斯股份有限公司 | Non-metallocene, its preparation method and use in olefin polymerization |
| CN1742028A (en) * | 2003-01-28 | 2006-03-01 | 托塔尔石油化学产品研究弗吕公司 | Group III bridged ionic metallocene based on cyclopentadienyl-fluorenyl ligands |
| CN102083844A (en) * | 2008-06-02 | 2011-06-01 | 尤米科尔股份公司及两合公司 | Process for preparing dienyl-ruthenium complexes |
| CN102964390A (en) * | 2012-11-27 | 2013-03-13 | 中国科学院上海有机化学研究所 | Planar chiral ferrocene compound and synthetic method and application thereof |
| CN105254682A (en) * | 2015-11-10 | 2016-01-20 | 中国科学院上海有机化学研究所 | Planar chiral ferrocene compound, synthetic method and application |
| CN109721630A (en) * | 2017-10-31 | 2019-05-07 | 上海茂晟康慧科技有限公司 | A kind of synthetic method of Ugi ' s amine and its derivative |
Non-Patent Citations (1)
| Title |
|---|
| ALLAN T CASEY等，: "The electrochemical synthesis of metallocenes, polymethylmetallocenes, "open metallocenes" and metal phenylacetylides", 《APPLIED ORGAANOMETONIC CHEMIWY》 * |
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