(±)-2,3-bis(4-chlorophenyl)propanoic acid | 1743-54-0

• 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: (±)-2,3-bis(4-chlorophenyl)propanoic acid
• 英文别名: 2-Benzyl-3-<2-dimethylamino-ethyl>-inden；α,β-Bis-(4-chlorphenyl)-propionsaeure；2,3-bis-(4-chloro-phenyl)-propionic acid；2,3-Bis-(4-chlor-phenyl)-propionsaeure；2,3-Bis(4-chlorophenyl)propanoic acid
• CAS: 1743-54-0
• 化学式: C₁₅H₁₂Cl₂O₂
• 分子量: 295.165
• InChiKey: AKRGELYVEBEVGH-UHFFFAOYSA-N

物化性质

• 熔点：
  161-163 °C
• 沸点：
  401.7±35.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (±)-2,3-bis(4-chlorophenyl)propanoic acid 生成 2-(p-Chlor-phenyl)-6-chlor-indanon-(1)
  参考文献：
  名称：

  影响中枢神经系统的化合物。V.取代的3-二烷基氨基烷基茚。

  摘要：

  DOI：

  10.1021/jm00303a608
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (±)-2,3-bis(4-chlorophenyl)propanoic acid
  参考文献：
  名称：

  Chloro Analogs of Methadone

  摘要：

  DOI：

  10.1021/ja01176a013

文献信息

• Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
  作者：Ashot Gevorgyan、Marc F. Obst、Yngve Guttormsen、Feliu Maseras、Kathrin H. Hopmann、Annette Bayer

  DOI：10.1039/c9sc02467k

  日期：——

  A caesium fluoride-mediated hydrocarboxylation of olefins is disclosed that does not rely on precious transition metal catalysts and ligands. The reaction occurs at atmospheric pressures of CO2 in the presence of 9-BBN as a stoichiometric reductant. Stilbenes, β-substituted styrenes and allenes could be carboxylated in good yields. The developed methodology can be used for preparation of commercial

  公开了不依赖贵重的过渡金属催化剂和配体的氟化铯介导的烯烃的加氢羧化。在9-BBN作为化学计量还原剂的情况下，反应在CO2的大气压下进行。丁苯酯，β-取代的苯乙烯和丙二烯可以高收率被羧化。所开发的方法可用于制备商业药物以及用于克规模的加氢羧化。计算研究表明，该反应是通过形成有机铯中间体而发生的。
• 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.