ethyl (2Z)-2-(bromomethyl)-3-(4-ethylphenyl)prop-2-enoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-2-(bromomethyl)-3-(4-ethylphenyl)prop-2-enoate
• 英文别名: ethyl (Z)-2-(bromomethyl)-3-(4-ethylphenyl)prop-2-enoate
• 化学式: C₁₄H₁₇BrO₂
• 分子量: 297.192
• InChiKey: CDBBSSZTYNUCJI-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-2-(bromomethyl)-3-(4-ethylphenyl)prop-2-enoate 、 4,6-二甲基-2-巯基嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到(Z)-ethyl 2-((4, 6-dimethylpyrimidin-2-ylthio)methyl)-3-(4-ethylphenyl)acrylate
  参考文献：
  名称：

  Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors

  摘要：

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.073
• 作为产物：
  描述：

  4-乙基苯甲醛 在 三乙烯二胺 、 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (2Z)-2-(bromomethyl)-3-(4-ethylphenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors

  摘要：

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.073

文献信息

• A Rapid and Efficient Stereoselective Synthesis of (Z)- and (E)-Allyl Bromides fromBaylis–Hillman Adducts Using Bromo(dimethyl)sulfonium Bromide
  作者：Biswanath Das、Katta Venkateswarlu、Maddeboina Krishnaiah、Harish Holla、Anjoy Majhi

  DOI：10.1002/hlca.200690141

  日期：2006.7

  Treatment of Baylis–Hillman adducts 1 with bromo(dimethyl)sulfonium bromide, Br(Me2)S+Br−, in MeCN was found to stereoselectively afford (Z)- and (E)-allyl bromides 2. The reaction is rapid at room temperature, high-yielding, and highly stereoselective.

  的治疗的Baylis-希尔曼加合物1与溴（二甲基）溴化锍，溴（ME 2）s +溴- ，在MeCN发现立体选择性地得到（Ž） -和（ë） -烯丙基溴化物2。该反应在室温下快速，高产率且高度立体选择性。