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Process for preparing (z)-3'-hydroxy-3, 4, 4', 5-tetranetgixy diphenyl ethylene

A technology of tetramethoxystilbene and methoxyphenyl, which is applied in the field of preparation of -3'-hydroxyl-3, can solve the problems of difficult to buy, expensive, and expensive isovanillin, and achieve cis-trans Improved selectivity, less environmental pollution, and reduced reaction costs

Inactive Publication Date: 2005-05-18
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Above-mentioned Perkin method is raw material with expensive 3,4,5-trimethoxyphenylacetic acid, and this raw material is difficult to buy and the price is extremely expensive on the market, and self-preparation then needs to use highly toxic substances such as sodium cyanide, Another raw material isovanillin is also more expensive

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  • Process for preparing (z)-3'-hydroxy-3, 4, 4', 5-tetranetgixy diphenyl ethylene
  • Process for preparing (z)-3'-hydroxy-3, 4, 4', 5-tetranetgixy diphenyl ethylene
  • Process for preparing (z)-3'-hydroxy-3, 4, 4', 5-tetranetgixy diphenyl ethylene

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Embodiment 1

[0036] Take 10.2g (0.061mol) of p-methoxyphenylacetic acid in a three-necked flask, add 20mL of glacial acetic acid to dissolve it, then add 3.6mL of bromine (11.2g, 0.068mol) dropwise, drop it for 45 minutes, and then stir in an ice bath After 1 hour, it was poured into ice water, and the solid was precipitated, filtered, and dried to obtain 14.8 g of 3-bromo-4-methoxy-phenylacetic acid, with a yield of 98.3%, and recrystallized with ethanol-water to obtain white flaky crystals. The yield is 70%, and the melting point is 113-114°C (literature value is 114-115°C).

[0037]Weigh 4.92g (0.02mol) of the obtained 3-bromo-4-methoxyphenylacetic acid, and add 4.32g (0.022mol) of 3,4,5-trimethoxybenzaldehyde into the reaction flask, and use 20mL Acetic anhydride was dissolved, and 5.0 mL of triethylamine was added dropwise, heated to 130°C, and reacted for 5 hours. After acidification with concentrated hydrochloric acid, it was poured into ice water to precipitate a solid, and the ob...

Embodiment 2

[0040] Embodiment 2: the compound melting point that embodiment 1 obtains and spectral data determination

[0041] The measurement results are as follows: mp116-117°C (literature value 115-116°C). Ms m / z(%): 316(M + , 100), 301(75). 1 H NMR (δ, ppm, J / Hz): 6.91 (d, 1H, J=2.0); 6.79 (dd, 1H, J=8, 2.0); 6.71 (d, 1H, J=8.0); 6.51 (s , 2H); 6.45(d, 1H, J=12.4); 6.42(d, 1H, J=12.4); 5.49(s, 1H); 3.89(s, 3H); 3.84(s, 3H); 3.68(s , 6H). IR (KBr): 3424, 3002, 2938, 2836, 1610, 1579, 1508, 1459, 1419, 1328, 1182, 1025, 1004, 944, 881, 854, 796, 765. From the above results, it was proved that the compound was (Z)-3'-hydroxy-3,4,4',5-tetramethoxystilbene.

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Abstract

The preparation process of (2)-3'-hydroxy-3, 4, 4', 5-tetramethoxy diphenyl ethylene includes bromizing cheap methoxy phenylacetic acid material to obtain 3-bromo-4-methoxy phenylacetic acid; condensation with 3, 4, 5-trimethoxy phenylaldehyde to obtain (E)-3-(3', 4', 5-trimethoxy phenyl)-2-(3'-bromo-4'-methoxy phenyl)-acrylic acid; phenol hydroxy substitution and debromination to obtain (E)-3-(3', 4', 5-trimethoxy phenyl)-2-(3'-hydroxy-4'-methoxy phenyl)-acrylic acid; and final decarboxyilation to obtain (Z)-3'-hydroxy-3, 4, 4', 5-tetramethoxy diphenyl ethylene. The present invention provides one new design thought of introducing phenol hydroxy radical into diphenyl ethylene compound and one new method of synthesizing (Z)-3'-hydroxy-3, 4, 4', 5-tetramethoxy diphenyl ethylene. The present invention has lowered cost, simplified post-treatment and high total yield.

Description

technical field [0001] The present invention relates to a process for preparing (Z)-3'-hydroxy-3,4,4',5-tetramethoxystilbene. Background technique [0002] (Z)-3'-hydroxy-3,4,4',5-tetramethoxystilbene (Combretastatin A-4, see formula (1) for structure) is a polyhydroxy stilbene natural product. Studies have confirmed that the compound can selectively inhibit tubulin polymerization and anti-mitosis, has strong anti-tumor activity, and is known as a blood vessel targeting agent. Its water-soluble phosphorylated prodrug has entered phase II clinical research in the United States and Europe, and has great market potential. Obviously, plant extraction alone cannot meet the needs of clinical research and marketing. Therefore, the research on the chemical synthesis method of this compound has important practical significance. [0003] [0004] Formula 1) [0005] Professor Pettit of Arizona State University and others have made a series of reports on the bi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C43/253
Inventor 邹永钟荣清张学景何树杰
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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