methyl (Z)-2-chloromethyl-3-(4-trifluoromethylphenyl)propenoate | 847653-90-1

• 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)-2-chloromethyl-3-(4-trifluoromethylphenyl)propenoate
• 英文别名: methyl (Z)-2-chloromethyl-3-(4-trifluoromethylphenyl)prop-2-enoate；methyl (Z)-2-(chloromethyl)-3-[4-(trifluoromethyl)phenyl]prop-2-enoate
• CAS: 847653-90-1
• 化学式: C₁₂H₁₀ClF₃O₂
• 分子量: 278.658
• InChiKey: NFICKCVAHGDQJC-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-chloromethyl-3-(4-trifluoromethylphenyl)propenoate 在 四丁基溴化铵 Cyclodextrin-B 作用下， 以 四氢呋喃 为溶剂， -20.0 ℃ 、82.74 kPa 条件下， 反应 0.42h， 生成 (R)-methyl 3-(4-trifluoromethylphenyl)-2-methylenepentanoate
  参考文献：
  名称：

  Expedient synthesis of β,β-disubstituted α-methylenepropionates

  摘要：

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.002
• 作为产物：
  描述：

  methyl 2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)acrylate 在 N,N-二甲基甲酰胺 草酰氯 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以69%的产率得到methyl (Z)-2-chloromethyl-3-(4-trifluoromethylphenyl)propenoate
  参考文献：
  名称：

  Expedient synthesis of β,β-disubstituted α-methylenepropionates

  摘要：

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.002

文献信息

• Enantioselective Preparation of ?,?-Disubstituted ?-Methylenepropionates by MAO Promotion of the Zinc Schlenk Equilibrium
  作者：Paul J. Goldsmith、Simon J. Teat、Simon Woodward

  DOI：10.1002/anie.200463028

  日期：2005.4.8
• Expedient synthesis of β,β-disubstituted α-methylenepropionates
  作者：Kallolmay Biswas、Christoph Börner、Josepe Gimeno、Paul J. Goldsmith、Daniella Ramazzotti、Angela L.K. So、Simon Woodward

  DOI：10.1016/j.tet.2004.12.002

  日期：2005.2

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.