(E)-4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid | 84249-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid
• 英文别名: 4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid；(E)-3-(2,3,4-Trimethoxybenzoyl)acrylic acid；(E)-4-oxo-4-(2,3,4-trimethoxyphenyl)but-2-enoic acid
• CAS: 84249-56-9
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: RAALLIPYMQYGLP-FNORWQNLSA-N

物化性质

• 熔点：
  161 °C(Solv: benzene (71-43-2))
• 沸点：
  460.3±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  巯基乙酸 、 (E)-4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid 生成 2-Carboxymethylsulfanyl-4-oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid
  参考文献：
  名称：

  2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Suppressed Survival of Neoplastic Human HeLa Cells: A QSAR Study

  摘要：

  DOI：

  10.1080/10426500590913294
• 作为产物：
  描述：

  2',3',4'-三甲氧基苯乙酮 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 95.0 ℃ 、6.67 kPa 条件下， 反应 4.5h， 生成 (E)-4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids

  摘要：

  DOI：

  10.1016/0223-5234(88)90166-3

文献信息

• Treatment of gastric and gastro-duodenal disorders with derivatives of
  申请人：Roussel Uclaf

  公开号：US04436752A1

  公开（公告）日：1984-03-13

  Gastric and gastro-duodenal disorders are treated by administering a compound of formula (I) ##STR1## in which A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydroxy radical, and in which R represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms, in the various possible stereoisomeric forms, as well as the pharmaceutically acceptable alkali metal, alkaline earth metal or amine salts of the compound of formula (I) in which R represents a hydrogen atom.

  胃和胃十二指肠疾病的治疗是通过给予化合物(I)的方式进行的##STR1##其中A和B共同表示双键，或者A表示氢原子，B表示羟基自由基，R表示氢原子或含有1至5个碳原子的烷基基团，以各种可能的立体异构体形式存在，以及在其中R表示氢原子的药用可接受的碱金属、碱土金属或胺盐。
• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Selectively Suppressed Proliferation of Neoplastic Human HeLa Cells. A SAR/QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Tatjana P. Stanojković、Ivan O. Juranić

  DOI：10.1021/jm0502889

  日期：2005.8.1

  A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 mu M/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations (< 2 mu M/L). The most active compounds exert lower cytotoxicity toward healthy human peripheral blood mononuclear cells (PBMC and PBMC+PHA) (selectivity indexes > 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.
• PROCESS FOR THE PREPARATION OF ALKYL BENZOYLACRYLATES
  申请人：Clariant (France) S.A.

  公开号：EP1363869A2

  公开（公告）日：2003-11-26
• US4436752A
  申请人：——

  公开号：US4436752A

  公开（公告）日：1984-03-13
• [EN] PROCESS FOR THE PREPARATION OF ALKYL BENZOYLACRYLATES<br/>[FR] PROCEDE DE PREPARATION DE BENZOYLACRYLATES D'ALKYLE
  申请人：CLARIANT FRANCE SA

  公开号：WO2002067847A2

  公开（公告）日：2002-09-06

  Process for the preparation of alkyl benzoylacrylates of formula (I) where R = alkyl, in which the reaction is carried out in an acid medium in the same reactor, without isolating the intermediate products, as follows: condensation of acetophenone with glyoxylic acid, elimination of a water/acetophenone mixture, elimination of the excess acetophenone, esterification with an alcohol in the presence of a strong acid, addition of a solvent, elimination of a mixture constituted by water, solvent and alcohol, dehydration by azeotropic distillation of the water, neutralization of the strong acid with a basic aqueous solution, decanting and concentration of the organic phase and recovery of the sought final product of formula (I).