CN106242936A - One class is to diphenylethyllene benzene and to benzene divinyl analog derivative and preparation method thereof - Google Patents
One class is to diphenylethyllene benzene and to benzene divinyl analog derivative and preparation method thereof Download PDFInfo
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- C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Abstract
One class is to diphenylethyllene benzene and to benzene divinyl analog derivative and preparation method thereof, and the general structure of a described class p-divinyl benzene derivant has two kinds: be respectivelyWithWherein R1For hydrogen, nitro, methoxyl group, chlorine, R2For hydrogen, methoxyl group, nitro, chlorine, R3For hydrogen, hydrogen, methyl, methoxyl group, dimethylamino, bromine, aldehyde radical, methyl formate base, methylsulfonyl, R4For hydrogen, methoxyl group, nitro, R5For hydrogen, nitro, methoxyl group, chlorine, R6It is 2 furyls, N ethyl 2 carbazyl, 2 quinolyls, diphenyl.The derivant of the present invention application prospect in fields such as biological medicine, optical function material, military affairs, optical storage is tempting, and to developing drug resource further, fluorescent material, nonlinear material have positive effect.
Description
Technical field
The invention belongs to technical field of chemistry, be specifically related to a class to diphenylethyllene benzene and to benzene divinyl analog derivative
And preparation method thereof.
Background technology
Before laser comes out, (1931) Gopper-mayer just foretells an atom on the basis of quantum theory
Or molecule can directly absorb two photon transitions to excited state by a kind of empty intermediate state (virtue state), it is derived there
The concept of two-photon absorption (Two-photo-absorb i.e. TPA).The appearance of laser demonstrates the prophesy of Gopper-mayer, from
This develops efficient non-linear absorbing material becomes the important topic of scientists.
Diphenylethylene compounds typically refers to containing the stilbene being connected by a vinyl between two phenyl ring female
The compound of body structure, this compounds has typical conjugated structure, and unique construction features and characteristic make it at medicine, food
The fields such as product, cosmetics, electronics, optics, dyestuff, material science have a wide range of applications.The substituted diphenylethylene of hydroxyl
Compound has significant antioxidation, antitumor, antiinflammatory, anti-Cardiovascular, estrogen-like effects, enhancing immunity more, delays
The physiologically actives such as aging, radiation protection.As benzene alkene not moral can be as treatment allergic dermatitis, the medicine of eczema, resveratrol can
As functional food additive, it is widely used in food and field of health care products, simultaneously because it has capture free radical, antioxygen
Change, absorb the characteristic of ultraviolet light, in terms of cosmetics, also show effect of brilliance.Additionally, diphenylethylene compounds is made
For organic photoelectric functional material because of the electronic structure of its uniqueness and performance, at organic electroluminescent, organic solid laser, photoelectric transfer
Many high-tech areas such as sensor, bio-imaging and optical dynamic therapy show great application prospect, have become as one
Emerging multi-crossed disciplines research frontier.Such as 4,4 '-dialkyl group-1,2-difluorodiphenyl ethylene compounds and end benzene
The para-position of ring is alkane or fluorine-based substituted 4-phenylacetylene base stilbene analog derivative is all good liquid crystal material；Fluoroform
Base, alkoxyl or alkoxynitro substituted stilbene analog derivative is the best organic non linear optical material；Hexichol
4 of ethylene compounds are with styryl, p-nitrophenyl vinyl or the substituted compound of p-methylstyrene base for having
Different emission and the luminescent material of color；Triazine radical amido diphenyl ethylene compounds and double benzothiazole stilbene are
The compound of agent structure is usually implemented as fluorescent whitening agent and is used for dye field.
Constantly finding and the continuous expansion of range of application of diphenylethylene compounds various active, has caused domestic
The great attention of outer organic synthesis research worker.Generally chemosynthesis diphenylethylene compounds includes several key point: how
Build stilbene ethylene bridge and how highly selective obtain the stilbene of single configuration.Therefore, suitably side is selected
It is very important that method highly selective prepares single configuration diphenylethylene compounds.
Summary of the invention
It is an object of the invention to provide in gentleer, economical and high selective under the conditions of prepare there is single structure
One class of type is to diphenylethyllene benzene and to benzene divinyl analog derivative.
The purpose of the present invention is achieved through the following technical solutions:
One class is to diphenylethyllene benzene and to benzene divinyl analog derivative, and the structure of such p-divinyl benzene derivant is led to
Formula has two kinds, and formula I is:
Wherein: R1For hydrogen, nitro, methoxyl group, chlorine,
R2For hydrogen, methoxyl group, nitro, chlorine,
R3For hydrogen, hydrogen, methyl, methoxyl group, dimethylamino, bromine, aldehyde radical, methyl formate base, methylsulfonyl,
R4For hydrogen, methoxyl group, nitro,
R5For hydrogen, nitro, methoxyl group, chlorine；
Formula II is:
Wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-quinolyl, diphenyl.
A class of the present invention is to diphenylethyllene benzene and as follows to the preparation method of benzene divinyl analog derivative:
A, being reacted with aromatic aldehyde by the phosphonium salt of structure shown in following structure formula III, condition is nitrogen protection, and sodium hydride makees alkali,
Dry toluene makees reaction 24 hours at solvent 110 DEG C, wherein: R1For hydrogen, nitro, methoxyl group, chlorine, R2For hydrogen, nitro, methoxyl group,
Chlorine, R3For hydrogen, methyl, bromine, methoxyl group, dimethylamino, aldehyde radical, methyl formate base, methylsulfonyl, R4For hydrogen, methoxyl group, R5For hydrogen,
Chlorine, methoxyl group,
Obtain formula I describe following 1-15 totally 15 to benzene divinyl analog derivative:
B, by structure shown in following structure formula IV phosphonium salt react with corresponding aldehydes or ketones, condition be nitrogen protection, hydrogen
Changing sodium and make alkali, dry toluene makees reaction 24 hours at solvent 110 DEG C, wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-
Quinolyl, diphenyl,
Obtain formula II describe following 16-19 totally 4 to benzene divinyl derivant:
The present invention based on Witting reaction, in gentleer, economical and high selective under the conditions of prepare there is list
One class of one configuration is to diphenylethyllene benzene and to benzene divinyl analog derivative.This compounds is that a class has two-photon absorption
To diphenylethyllene benzene and to benzene divinyl analog derivative, at biological medicine, optical function material, military affairs, optical storage, food
Product, cosmetics, electronics, optics, dyestuff, organic electroluminescent, organic solid laser, photoelectric sensor, bio-imaging and light
Many high-tech areas such as dynamic therapy show great application prospect, to developing drug resource, fluorescent material, non-further
Linear material has positive effect.
Accompanying drawing explanation
Fig. 1 is the crystal structure of the product determined by X-ray single crystal diffraction.
Detailed description of the invention
A class of the present invention is to diphenylethyllene benzene and to benzene divinyl analog derivative, and such is to benzene divinyl derivant
General structure have two kinds, formula I is:
Wherein: R1For hydrogen, nitro, methoxyl group, chlorine,
R2For hydrogen, methoxyl group, nitro, chlorine,
R3For hydrogen, hydrogen, methyl, methoxyl group, dimethylamino, bromine, aldehyde radical, methyl formate base, methylsulfonyl,
R4For hydrogen, methoxyl group, nitro,
R5For hydrogen, nitro, methoxyl group, chlorine；
Formula II is:
Wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-quinolyl, diphenyl.
The preparation method of benzene divinyl analog derivative to diphenylethyllene benzene and is distinguished as follows by an above-mentioned class:
A, being reacted with aromatic aldehyde by the phosphonium salt of structure shown in following structure formula III, condition is nitrogen protection, and sodium hydride makees alkali,
Dry toluene makees reaction 24 hours at solvent 110 DEG C, wherein: R1For hydrogen, nitro, methoxyl group, chlorine, R2For hydrogen, nitro, methoxyl group,
Chlorine, R3For hydrogen, methyl, bromine, methoxyl group, dimethylamino, aldehyde radical, methyl formate base, methylsulfonyl, R4For hydrogen, methoxyl group, R5For hydrogen,
Chlorine, methoxyl group,
Obtain formula I describe following 1-15 totally 15 to diphenylethyllene benzene derivative:
B, by structure shown in following structure formula IV phosphonium salt react with corresponding aldehydes or ketones, condition be nitrogen protection, hydrogen
Changing sodium and make alkali, dry toluene makees reaction 24 hours at solvent 110 DEG C, wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-
Quinolyl, diphenyl,
Obtain formula II describe following 16-19 totally 4 to benzene divinyl derivant:
Standby operational approach is as follows:
(E)-1,4-two (2,6-dichlorostyrene base) benzene (12):
Accurately weigh two methylene benzene two (bromination triphenylphosphine) (0.4g, 0.76mmol), NaH (0.218g,
9.02mmol) in 50mL round-bottomed flask, add toluene 40mL, under room temperature, stir 30min, when solution becomes yellow green, then
Adding 2,6-dichlorobenzaldehyde (0.266g, 1.52mmol), nitrogen is protected at 110 DEG C backflow 24h.Being cooled to room temperature, rotation is steamed
Remove solvent and obtain crude product.Crude by column chromatography silica gel 200-300 mesh is isolated and purified, and eluent is VDichloromethane: VPetroleum ether=4:7,
Obtain faint yellow solid 0.141g, productivity: 47%.Reaction equation is as follows:
The crystal structure of product is determined, such as Fig. 1 by X-ray single crystal diffraction.Bond distance: C (1)-Cl (2),C
(5)-Cl(1),C(1)-C(2),C(2)-C(3),C(3)-C(4),C(4)-C
(5),C(5)-C(6),C(6)-C(7),C(7)-C(8),C(8)-C(9),C(9)-C(10),C(9)-C(11),C(10)-C(11),Bond angle: Cl (2)-
C(1)-C(6),118.97°；Cl(1)-C(5)-C(6),120.42°；C(6)-C(7)-C(8),125.12°；C(7)-C(8)-C
(9),127.24°；C(5)-C(6)-C(7),124.55°；C(1)-C(6)-C(7),120.67°；C(1)-C(2)-C(3),
119.51°；Cl(2)-C(1)-C(2),117.91°；C(8)-C(9)-C(10),123.68°.1H NMR(400MHz,DMSO)δ
(ppm) 7.74 7.64 (m, 2H), 7.57 7.50 (m, 4H), 7.48 (d, J=8.3Hz, 2H), 7.33 (dd, J=16.8,
8.5Hz, 2H), 7.13 (d, J=19.4Hz, 2H), 7.03 (d, J=8.3Hz, 2H).13C NMR(100MHz,DMSO)δ(ppm)
136.66,134.72–134.41,128.59,128.11,127.16,126.74,122.84.ESI-MS calcd for
C22H14Cl4[M+H]+421.16,found421.22,424.96。
(E)-1,4-two (N-ethyl carbazole-2-vinyl) benzene (19):
Accurately weigh two methylene benzene two (bromination triphenylphosphine) (0.202g, 0.38mmol), NaH (0.055g,
2.3mmol) in 50ml round-bottomed flask, add toluene 40ml, under room temperature, stir 30min, when solution becomes yellow chlorine color, add N-
Ethyl-2-carbazole formaldehyde (0.15g, 0.77mmol), nitrogen is protected at 110 DEG C backflow 24h.Being cooled to room temperature, rotation is evaporated off
Solvent obtains crude product.Crude by column chromatography silica gel 200-300 mesh is isolated and purified, and eluant is VDichloromethane: VPetroleum ether=5:2),
Yellow powder solid 0.124g, productivity: 45%.Reaction equation is as follows:
1H NMR(400MHz,CDCl3) δ (ppm) 8.28 (s, 2H), 8.17 (d, J=7.7Hz, 2H), 7.73 (d, J=
8.5Hz, 2H), 7.60 (s, 4H), 7.51 (t, J=7.3Hz, 2H), 7.45 (d, J=6.0Hz, 3H), 7.41 (d, J=7.3Hz,
2H), 7.36 (s, 1H), 7.28 (d, J=14.2Hz, 2H), 7.20 (d, J=16.2Hz, 2H), 4.41 (q, J=7.2Hz, 4H),
1.57(s,6H).13C NMR(100MHz,CDCl3)δ(ppm)140.3,139.0,134.4,128.59,128.11,127.16,
126.74,125.4,123.6,122.4,120.4,118.0,115.5,109.0,108.3,106.3,37.4,13.8.ESI-MS
calcd for C38H32N2[M+H]+517.67,found 517.69。
Claims (2)
1. a class is to diphenylethyllene benzene and to benzene divinyl analog derivative, it is characterised in that such p-divinyl benzene derives
The general structure of thing has two kinds, and formula I is:
Wherein: R1For hydrogen, nitro, methoxyl group, chlorine,
R2For hydrogen, methoxyl group, nitro, chlorine,
R3For hydrogen, hydrogen, methyl, methoxyl group, dimethylamino, bromine, aldehyde radical, methyl formate base, methylsulfonyl,
R4For hydrogen, methoxyl group, nitro,
R5For hydrogen, nitro, methoxyl group, chlorine；
Formula II is:
Wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-quinolyl, diphenyl.
The preparation method of a class p-divinyl benzene derivant the most as claimed in claim 1, it is characterised in that preparation method is such as
Under:
A, being reacted with aromatic aldehyde by the phosphonium salt of structure shown in following structure formula III, condition is nitrogen protection, and sodium hydride makees alkali, anhydrous
Reaction 24 hours at solvent 110 DEG C made by toluene, wherein: R1For hydrogen, nitro, methoxyl group, chlorine, R2For hydrogen, nitro, methoxyl group, chlorine,
R3For hydrogen, methyl, bromine, methoxyl group, dimethylamino, aldehyde radical, methyl formate base, methylsulfonyl, R4For hydrogen, methoxyl group, R5For hydrogen, chlorine,
Methoxyl group,
Obtain formula I describe following 1-15 totally 15 to diphenylethyllene benzene derivative:
B, by structure shown in following structure formula IV phosphonium salt react with corresponding aldehydes or ketones, condition be nitrogen protection, sodium hydride
Making alkali, dry toluene makees reaction 24 hours at solvent 110 DEG C, wherein: R6For 2-furyl, N-ethyl-2-carbazyl, 2-quinoline
Base, diphenyl,
Obtain formula II describe following 16-19 totally 4 to benzene divinyl derivant:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998021521A1 (en) * | 1996-11-12 | 1998-05-22 | California Institute Of Technology | Two-photon or higher-order absorbing optical materials and methods of use |
| WO2010115080A2 (en) * | 2009-04-02 | 2010-10-07 | The Johns Hopkins University | Self-assembling peptides bearing organic electronic functionality and applications employing the same |
| WO2012002911A1 (en) * | 2010-06-29 | 2012-01-05 | National University Of Singapore | Methods and compositions for cellular imaging and cancer cell detection using light harvesting conjugated polymer- biomolecular conjugates |
-
2016
- 2016-08-03 CN CN201610628788.XA patent/CN106242936A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998021521A1 (en) * | 1996-11-12 | 1998-05-22 | California Institute Of Technology | Two-photon or higher-order absorbing optical materials and methods of use |
| WO2010115080A2 (en) * | 2009-04-02 | 2010-10-07 | The Johns Hopkins University | Self-assembling peptides bearing organic electronic functionality and applications employing the same |
| WO2012002911A1 (en) * | 2010-06-29 | 2012-01-05 | National University Of Singapore | Methods and compositions for cellular imaging and cancer cell detection using light harvesting conjugated polymer- biomolecular conjugates |
Non-Patent Citations (5)
| Title |
|---|
| C. O. SANCHEZ等: "Electronic and structural properties of polymersbased on phenylene vinylene and thiophene units. Control of the gap by gradual increases ofthiophene moieties", 《NEW J. CHEM.》 * |
| CUI JIANZHONG等: "Synthesis and light-emitting properties of organic electroluminescent compounds and their metal complexes", 《CHINESE SCIENCE BULLETIN 》 * |
| HIROYUKI MOCHIZUKI等: "Emission behavior of trifluoromethyl bisstyrylbenzene derivative", 《JAPANESE JOURNAL OF APPLIED PHYSICS》 * |
| KENICHIRO ITAMI等: "Triarylethene-Based Extended π-Systems: Programmable Synthesis and Photophysical Properties", 《J. ORG. CHEM.》 * |
| STN: "CAS", 《STN REGISTRY DATABASE》 * |
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