Method for preparing trans-diphenylethylene compound

A technology of stilbene and compounds, which is applied in the field of preparation of organic compounds, can solve the problems of poor compatibility of different functional groups and low yield of trans-stilbene products, and achieve variable structure, good compatibility, The effect of mild synthetic conditions

Inactive Publication Date: 2017-07-14
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The defects of the above-mentioned technology mainly include: the reaction needs to use two different raw materials; the reaction needs to be carried out at a higher temperature; the double bond generated contains both cis and trans isomers; Good and trans-stilbene products yield is not high

Method used

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  • Method for preparing trans-diphenylethylene compound
  • Method for preparing trans-diphenylethylene compound
  • Method for preparing trans-diphenylethylene compound

Examples

Experimental program
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preparation example Construction

[0039] (1) Preparation of raw materials

[0040] All gem-dibromomethyl arene compounds can be prepared by existing common synthesis methods, and the molecular structure of the gem-dibromomethyl arene compounds used in the examples is shown in the following formula.

[0041]

[0042] Raw compound abbreviation R 1

R 2

R 3

1a H- H- H- 1b H- CH 3 -

H- 1c H- CH 3 CH 2 -

H- 1d H- tert-C 4 h 9 -

H- 1e H- CH 3 OC(O)-

H- 1f H- CH 3 CH 2 OC(O)-

H- 1g H- CH 3 C(O)-

H- 1h H- CH 3 COO-

H- 1i H- Ph-trans-CH=CH-C(O)- H- 1j CH 3 O-

H- H- 1k H- Ph-i-C 3 h 6 -

H- 1l CH 3 O-

CH 3 O-

CH 3 O-

[0043] (2) Synthesis method

[0044] Deoxidize a certain stoichiometric ratio of gem-dibromomethyl aromatic compounds, polyamines, and copper powder (it can also be replaced with copper wire or copper sheet) in the reaction flask...

Embodiment 1

[0051] The synthesis of embodiment 1 dibromotoluene (1a)

[0052] Dissolve 3 mL of benzaldehyde (30 mmol) in 30 mL of CH 2 Cl 2 Add 30mL of 1.2M BBr slowly dropwise under stirring at 0℃ 3 CH 2 Cl 2 The solution (36 mmol) was dropped in 0.5 hours, and the temperature was raised to 25° C. to continue the reaction for 3 hours. The reaction solution was light orange, and white waxy globular solids settled out at the bottom. The reaction was stopped. After filtering, the filtrate was passed through a 200-300 mesh silica gel column, rinsed with petroleum ether, and the eluent was concentrated to obtain colorless transparent droplets. After vacuum drying at room temperature, 5.1 g of light yellow droplets were obtained, with a yield of 68%. 1 H NMR (400MHz, CDCl 3 ,ppm): δ=7.56(d,2H,ArH),7.37(m,3H,ArH),6.65(s,1H,ArCHBr 2 ).

Embodiment 2

[0053] The synthesis of embodiment 2 methyl dibromomethylbenzoate (1e)

[0054] 1.500g methyl p-toluate (10mmol), 3.920g NBS (22mmol) and 0.266g BPO (1.1mmol), 60mL CCl 4 Sequentially added to a 100mL three-necked flask, the system was ventilated with nitrogen for 15 minutes, and refluxed for 3 hours to stop the reaction. After filtration, the filtrate was concentrated to obtain a light yellow solid. The crude product was recrystallized from n-hexane to obtain 707 mg of white crystals with a yield of 23%. 1 H NMR (400MHz, CDCl 3 ,ppm): δ=8.04(d,2H,ArH),7.65(d,2H,ArH),6.66(s,1H,ArCHBr 2 ),3.93(s,3H,-OCH 3 ). EA: Calcd. For C 9 h 8 Br 2 o 2 C(%): 35.10, H(%): 2.62. Found C(%): 35.42, H(%): 2.54.

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Abstract

The invention relates to a preparation method of organic compounds and provides a method for preparing a trans-diphenylethylene compound. The method comprises adding a gem-dibromomethyl aromatic hydrocarbon compound, copper and polyamine into a reactor in the presence of a solvent, carrying out deoxidizing treatment, adding an oxygen-free water-free solvent into the reactor, carrying out a coupling reaction process to obtain C-C- double bonds, and carrying out separation and purification to obtain the trans-diphenylethylene compound. The method has mild synthesis conditions and has good reaction compatibility to different functional groups. The gem-dibromomethyl aromatic hydrocarbon compound as a raw material is easy to synthesize, may have different substituent groups and has a variable structure. The product obtained by coupling a raw material can be simply treated and has high purity. The asymmetric trans-diphenylethylene compound can be prepared from two different raw materials.

Description

technical field [0001] The invention relates to the field of preparation methods of organic compounds, in particular to a new synthesis method of trans-diphenylethylene compounds. Background technique [0002] The stilbene compound is shown in the following formula, has a conjugated structure, and has a wide range of applications in the fields of medicine, food, and material science. In particular, polyhydroxyl-substituted stilbenes and methoxylated products have significant antioxidant, anti-tumor, anti-inflammatory, and anti-cardiovascular effects. In addition, the typical conjugated structure of stilbene compounds makes them widely used in the fields of electronics, nonlinear optics, luminescent materials and dyes. [0003] [0004] There are many synthetic methods of stilbene compounds, which can be mainly divided into two categories. The first type is obtained by oxidation or reduction reaction using a diaryl substituted compound as a raw material; the other method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/26C07C15/52C07C41/24C07C43/215C07C45/65C07C49/796C07C67/317C07C69/76C07C67/297C07C69/16
CPCC07C1/26C07C17/269C07C41/24C07C41/30C07C45/65C07C45/72C07C67/293C07C67/297C07C67/317C07C67/343C07C15/52C07C22/04C07C43/225C07C43/215C07C49/813C07C49/796C07C69/76C07C69/63C07C69/16
Inventor 王齐曹花
Owner ZHEJIANG UNIV
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