methyl (E)-2-(4-chlorophenyl)-3-phenylprop-2-enoate | 50415-79-7

• 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: methyl (E)-2-(4-chlorophenyl)-3-phenylprop-2-enoate
• 英文别名: 2-(4-chloro-phenyl)-3t-phenyl-acrylic acid methyl ester；2-(4-Chlor-phenyl)-3t-phenyl-acrylsaeure-methylester；3t-Phenyl-2-(4-chlor-phenyl)-acrylsaeure-methylester
• CAS: 50415-79-7
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: VZFCJBKLZZPKOU-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  methyl (E)-2-(4-chlorophenyl)-3-phenylprop-2-enoate 生成 2-(4-chlorophenyl)-3-phenylpropenoic acid
  参考文献：
  名称：

  Meerwein; Buechner; van Emster, Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 152, p. 237,265

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3R)-3-Chloro-2-(4-chloro-phenyl)-3-phenyl-propionic acid methyl ester 在 2,4,6-三甲基吡啶 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 methyl (E)-2-(4-chlorophenyl)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Allard,M.; Levisalles,J., Bulletin de la Societe Chimique de France, 1972, p. 1921 - 1925

  摘要：

  DOI：

文献信息

• General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters
  作者：Hidefumi Nakatsuji、Hiroshi Nishikado、Kanako Ueno、Yoo Tanabe

  DOI：10.1021/ol9013359

  日期：2009.10.1

  for α,β-disubstituted α,β-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti−Claisen condensation (formylation) of esters to give α-formyl esters (12 examples, 60−99%), (ii) (E)- and (Z)-stereocomplementary enol p-toluenesulfonylation (tosylation) using TsCl−N-methylimidazole (NMI)−Et3N and LiOH (24 examples, 82−99%), and (iii) stereoretentive Suzuki−Miyaura cross-coupling

  α，β-二取代的α，β-不饱和酯的（E）-和（Z）-立体互补制备方法是通过三个常规且稳健的反应顺序进行的：（i）酯的Ti-Claisen缩合（甲酰化）得到α -甲酰基酯（12个例子，60-99％），（ii）（E）-和（Z）-立体互补烯醇对甲苯磺酰化（甲苯磺酸化），使用TsCl- N-甲基咪唑（NMI）-Et 3 N和LiOH（24实例82-99％）和（iii）立体保持Suzuki-Miyaura交叉耦合（18实例64-96％）。
• Triethylamine-induced Reactions of Methyl 2,3-Dibromo-2,3-diarylpropanoates in Methanol†
  作者：Mercedes A. Badajoz、Rosana S. Montani、Mercedes C. Cabaleiro

  DOI：10.1039/a706372e

  日期：——

  The title compounds undergo elimination with methanolic triethylamine to afford the corresponding debrominated olefins, most of them through an E2 stereoconvergent process.

  这些标题化合物与甲醇三乙胺发生脱溴反应，生成相应的去溴烯烃，其中大多数是通过E2立构转化过程生成的。
• P(NMe₂)₃-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters
  作者：Sunewang Rixin Wang、Alexander T. Radosevich

  DOI：10.1021/acs.orglett.5b01784

  日期：2015.8.7

  A commercial phosphorus-based reagent (P(NMe2)(3)) mediates,umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barer-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated, by a two-electron redox addition of the tricoordinate phosphorus reagent with an alpha-keto ester Compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.
• 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.
• Badajoz, Mercedes A.; Montant, Rosana S.; Cabaleiro, Mercedes C., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1996, vol. 8, p. 1717 - 1722
  作者：Badajoz, Mercedes A.、Montant, Rosana S.、Cabaleiro, Mercedes C.

  DOI：——

  日期：——