methyl (E)-3-chloro-3-phenylprop-2-enoate | 116373-35-4

• 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: methyl (E)-3-chloro-3-phenylprop-2-enoate
• 英文别名: methyl (E)-3-chloro-3-phenylacrylate；β-chloro-cis-cinnamic acid methyl ester；β-Chlor-cis-zimtsaeure-methylester；(E)-Methyl 3-chlorcinnamat
• CAS: 116373-35-4
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: VVKKGLQPLPGURF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯丙炔酸 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 环己烷 、 丙酮 为溶剂， 反应 19.17h， 生成 methyl (E)-3-chloro-3-phenylprop-2-enoate 、 methyl (Z)-3-chloro-3-phenylprop-2-enoate
  参考文献：
  名称：

  One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation

  摘要：

  The reactions of esters and amides of 3-phenylpropynoic acid with strong Lewis acids AIX(3) (X = Cl, Br) or conjugate Bronsted-Lewis superacids HX-AIX(3) (X = Cl, Br) in benzene and cyclohexane at room temperature afforded 3,3-diphenylpropanoic acid derivatives in up to 94% yield. This tandem reaction of the acetylene bond proceeded by hydrophenylation followed by ionic hydrogenation. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.09.026

文献信息

• Novel Stereospecific Synthesis of 3-Chloroacrylate Esters via Palladium-Catalyzed Carbonylation of Terminal Acetylenes
  作者：Jinheng Li、Huanfeng Jiang、Aiqun Feng、Lanqi Jia

  DOI：10.1021/jo982345u

  日期：1999.8.1

  A simple and effective method for the highly regio- and stereospecific synthesis of (Z)-3-chloroacrylate esters is described. Using terminal acetylenes and primary, secondary, and tertiary aliphatic alcohols as substrates, the carbonylation reactions were carried out under carbon monoxide (1 atm) at room temperature in the presence of a catalytic amount of PdCl2 and 3 equiv of cupric chloride. Isolated yields of (Z)-3-chloroacrylate esters ranging 6 om 30% to 72% were obtained. Our results show that the polarity of the alcohol-benzene solvent plays an important role in the stereochemistry of the products.
• Stoermer; Kirchner, Chemische Berichte, 1920, vol. 53, p. 1299
  作者：Stoermer、Kirchner

  DOI：——

  日期：——