methyl (Z)-3-chloro-3-phenylprop-2-enoate | 56377-29-8

• 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 (Z)-3-chloro-3-phenylprop-2-enoate
• 英文别名: (Z)-methyl 3-chloro-3-phenylacrylate；methyl (Z)-3-chloro-3-phenylacrylate；methyl 3-chlorocinnamate；β-chloro-trans-cinnamic acid methyl ester；β-Chlor-trans-zimtsaeure-methylester；3-chloro-3-phenyl-2-propenoic acid, methyl ester；(Z)-3-Chloro-3-phenyl-acrylic acid methyl ester
• CAS: 56377-29-8
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: VVKKGLQPLPGURF-CLFYSBASSA-N

物化性质

• 沸点：
  284.5±9.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-chloro-3-phenylprop-2-enoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 苯丙炔酸
  参考文献：
  名称：

  Youssef, Abdel-Hamid A.; Sharaf, Saber M.; El-Sadany, Samir K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 4, p. 359 - 361

  摘要：

  DOI：
• 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

• Chloroesterification of Enynes Catalyzed by NHC Rhodium Compounds
  作者：Young Chung、Ji Young Baek、Sang Lee、So Sim

  DOI：10.1055/s-2008-1032073

  日期：——

  An efficient rhodium N-heterocyclic carbene (NHC)-catalyzed chloroesterification of terminal alkynes and enynes has been developed. The reaction was highly regio- and stereospecific: the Z-isomer was obtained as the sole product.

  一种高效的铑N-杂环卡宾(NHC)催化末端炔烃及烯炔的氯酯化反应已被开发。该反应具有高度区域选择性和立体选择性：唯一产物为Z-异构体。
• Palladium-catalysed annulation of β-chloro-α,β-unsaturated esters with internal alkynes leading to 2H-pyran-2-ones
  作者：Ruimao Hua、Masato Tanaka

  DOI：10.1039/b007620l

  日期：——

  Heteroannulation of β-chloro-α,β-unsaturated esters with internal alkynes proceeded in the presence of triethylamine and palladium complexes, bis(triphenylphosphine)palladium species in particular, to afford to 2H-pyran-2-ones. Treatment of methyl (Z)-3-chloro-2-heptenoate with Pd(PPh3)4 generates [(Z)-1-butyl-2-methoxycarbonylethenyl]chlorobis(triphenylphosphine)palladium ia oxidative addition, which gives the corresponding 2H-pyran-2-one upon addition of 4-octyne. Terminal alkynes also reacted with β-chloro-α,β-unsaturated esters, but the major products were β-alkynylated α,β-unsaturated esters.

  在三乙胺和钯络合物（特别是双(三苯基膦)钯物种）的存在下，β-氯-α,β-不饱和酯与内炔进行杂环化反应，生成2H-吡喃-2-酮。用Pd(PPh3)4处理甲基(Z)-3-氯-2-庚烯酸酯，通过氧化加成生成[(Z)-1-丁基-2-甲氧羰基乙烯基]氯双(三苯基膦)钯，在加入4-辛炔后得到相应的2H-吡喃-2-酮。末端炔烃也能与β-氯-α,β-不饱和酯反应，但主要产物是β-炔基化的α,β-不饱和酯。
• General and Selective Synthesis of (<i>Z</i>)-3-Haloacrylates via Palladium-Catalyzed Carbonylation of Terminal Alkynes
  作者：Jin-Heng Li、Shi Tang、Ye-Xiang Xie

  DOI：10.1021/jo048358r

  日期：2005.1.1

  A general and selective palladium-catalyzed carbonylation of terminal alkynes method for the synthesis of (Z)-3-haloacrylates is presented. In the presence of a catalytic amount of PdX2 and 5 equiv of CuX2 (X = Cl and Br), terminal alkynes were carbonylated to afford the corresponding (Z)-3-haloacrylates exclusively in moderate to good yields. The results showed that the effect of solvent had a fundamental

  提出了一种通用的，选择性的钯催化的末端炔烃羰基化方法，用于合成（Z）-3-卤代丙烯酸酯。在催化量的PdX 2和5当量的CuX 2（X = Cl和Br）的存在下，末端炔烃被羰基化，仅以中等到良好的产率得到相应的（Z）-3-卤代丙烯酸酯。结果表明，溶剂的影响对钯催化的羰基化反应的化学选择性和立体选择性具有根本性的影响。
• Electrochemical cross-coupling of organic halides: Trichloromethylation and related synthesis of gem-dichloro compounds
  作者：J.Y. Nédélec、H. Ait-Haddou-Mouloud、J.C. Folest、J. Périchon

  DOI：10.1016/s0040-4039(00)82021-3

  日期：1988.1

  The cross-coupling of activated alkyl halides with carbon tetrachloride or substituted trichloromethanes can be obtained electrochemically in good yield in an undivided cell with a sacrificial anode.

  活性烷基卤化物与四氯化碳或取代的三氯甲烷的交叉偶联可以在具有牺牲阳极的未分隔电池中以良好的产率以电化学方式获得。
• The First Example of Rhodium(I)-Catalyzed Regio- and Stereoselective Chloroesterification of Alkynes with Chloroformate Esters
  作者：Ruimao Hua、Shigeru Shimada、Masato Tanaka

  DOI：10.1021/ja9822299

  日期：1998.12.1