trans-α-(2'-chlorophenyl)cinnamic acid | 728-04-1

• 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: trans-α-(2'-chlorophenyl)cinnamic acid
• 英文别名: cis-β-Phenyl-α-<2-chlor-phenyl>-acrylsaeure, trans-α-<2-Chlor-phenyl>-zimtsaeure；trans-2-<2-Chlor-phenyl>-3-phenyl-acrylsaeure；cis-α-<2-Chlor-phenyl>-zimtsaeure；(E)-2-(2-chlorophenyl)-3-phenylpropenoic acid；3t-phenyl-2-(2-chloro-phenyl)-acrylic acid；3t-Phenyl-2-(2-chlor-phenyl)-acrylsaeure；(E)-2-(2-chlorophenyl)-3-phenylprop-2-enoic acid
• CAS: 728-04-1
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: NEJQCIBPMRYSGX-JLHYYAGUSA-N

物化性质

• 熔点：
  175-178 °C
• 沸点：
  368.8±27.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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：

  trans-α-(2'-chlorophenyl)cinnamic acid 在 喹啉 、 氢氧化钾 作用下， 生成 菲-9-甲酸
  参考文献：
  名称：

  Process for producing compounds of the phenanthrene series

  摘要：

  公开号：

  US02109518A1
• 作为产物：
  描述：

  α-溴代肉桂醛 在 sodium chlorite 、 sodium dihydrogenphosphate 、 四(三苯基膦)钯 、 2-甲基-2-丁烯 、 sodium carbonate 作用下， 以 甲醚 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 trans-α-(2'-chlorophenyl)cinnamic acid
  参考文献：
  名称：

  通过钯催化的不对称 C-H 炔基化开发轴向手性苯乙烯型羧酸配体

  摘要：

  公开了一种用于开发新型轴向手性苯乙烯型羧酸的弱配位羧酸盐导向钯催化的阻转选择性 C-H 炔基化方法。这种转化表现出良好的产量（高达 85%）、出色的对映控制（高达 99% ee）和温和的条件。值得注意的是，所得炔基羧酸衍生物的合成效用通过各种衍生化以及它们在不对称 C-H 活化中作为手性配体的潜力得到了证明。

  DOI：

  10.1021/acs.orglett.1c02692

文献信息

• Reactions of Carbonyl Compounds in Basic Solutions. Part 34. The Mechanism of the Base-Catalysed Ring Fission of 2,3-Diphenylcycloprop-2-en-1-one
  作者：Keith Bowden、Emma J. Burgess

  DOI：10.1135/cccc19991594

  日期：——

  The rate coefficients for the base-catalysed ring fission of a series of 2-phenyl-3-(2-, 3- or 4-substituted phenyl)cycloprop-2-en-1-ones to give the corresponding (E)-2,3-diphenylacrylic acids have been determined in water at 30.0 °C, as well as for the unsubstituted compound at 40.0, 50.0 and 60.0 °C. The effects of meta- and para-substituents on the rates have been correlated using the Hammett equation to give a reaction constant, ρ, equal to ca 1.2 at 30 °C. For the unsubstituted compound, the activation parameters have been calculated and the kinetic solvent isotope effect has been studied. The effects of ortho-substituents on the rates appear to be mainly polar, rather than steric, in origin. The evidence indicates a mechanistic pathway which proceeds by addition of hydroxide anion to the ketone, which is rate-determining. The adduct suffers ring fission to give the final product via a carbanionic intermediate.

  一系列2-苯基-3-(2-, 3- 或 4-取代苯基)环丙烯酮在30.0°C的水中的碱催化环裂速率系数已确定，以及未取代化合物在40.0、50.0和60.0°C的速率系数。利用Hammett方程相关了对速率的间位和对位取代基的影响，得到在30°C时等于约1.2的反应常数ρ。对于未取代化合物，已计算了活化参数并研究了动力学溶剂同位素效应。取代基对速率的影响似乎主要是极性的，而不是立体的。证据表明，该机理途径通过氢氧根离子加成到酮中，这是决定速率的步骤。该加合物经历环裂，生成最终产物，通过一个碳负离子中间体。
• Wheeler; Batlle de Pabon, Journal of Organic Chemistry, 1965, vol. 30, p. 1473,1476
  作者：Wheeler、Batlle de Pabon

  DOI：——

  日期：——
• Kessar, S. V.; Nadir, U. K.; Pahwa, P. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 1, p. 7 - 9
  作者：Kessar, S. V.、Nadir, U. K.、Pahwa, P. S.、Singh, Paramjit、Gupta, Y. P.

  DOI：——

  日期：——
• 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.
• Development of Axially Chiral Styrene-Type Carboxylic Acid Ligands via Palladium-Catalyzed Asymmetric C–H Alkynylation
  作者：Chi Yang、Fei Li、Tian-Rui Wu、Ru Cui、Bing-Bing Wu、Ruo-Xing Jin、Yan Li、Xi-Sheng Wang

  DOI：10.1021/acs.orglett.1c02692

  日期：2021.11.5

  coordinated carboxylate-directed palladium-catalyzed atroposelective C–H alkynylation method for the development of novel axially chiral styrene-type carboxylic acids is disclosed. This transformation exhibits good yields (up to 85%), excellent enantiocontrol (up to 99% ee), and mild conditions. Notably, the synthetic utility of the resulting alkynyl carboxylic acid derivatives was demonstrated by various

  公开了一种用于开发新型轴向手性苯乙烯型羧酸的弱配位羧酸盐导向钯催化的阻转选择性 C-H 炔基化方法。这种转化表现出良好的产量（高达 85%）、出色的对映控制（高达 99% ee）和温和的条件。值得注意的是，所得炔基羧酸衍生物的合成效用通过各种衍生化以及它们在不对称 C-H 活化中作为手性配体的潜力得到了证明。