(E)-2-(2-chlorophenyl)-3-(4-chlorophenyl)prop-2-enoic acid | 1262329-36-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(2-chlorophenyl)-3-(4-chlorophenyl)prop-2-enoic acid
• CAS: 1262329-36-1
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: BROAEDLTHRKGJQ-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-chlorophenyl)-3-(4-chlorophenyl)prop-2-enoic acid 在 palladium/alumina 、 氢气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 21.84 ℃ 、100.0 kPa 条件下， 反应 4.0h， 生成 2-(2-chlorophenyl)-3-phenylpropionic acid 、 2-(2-Chlorophenyl)-3-(4-chlorophenyl)propanoic acid
  参考文献：
  名称：

  Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination

  摘要：

  The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O3. In contrast to the fast hydrodechlorination of the beta-phenyl-para-Cl substituted acids the Cl on the alpha-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the alpha- and beta-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the alpha-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the alpha-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.09.013

文献信息

• Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination
  作者：György Szőllősi、Beáta Hermán、Erika Szabados、Ferenc Fülöp、Mihály Bartók

  DOI：10.1016/j.molcata.2010.09.013

  日期：2010.12

  The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O3. In contrast to the fast hydrodechlorination of the beta-phenyl-para-Cl substituted acids the Cl on the alpha-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the alpha- and beta-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the alpha-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the alpha-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system. (C) 2010 Elsevier B.V. All rights reserved.