(Z)-2-Chloromethyl-3-phenyl-acrylic acid ethyl ester | 98748-51-7

• 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: (Z)-2-Chloromethyl-3-phenyl-acrylic acid ethyl ester
• 英文别名: ethyl 2-(chloromethyl)-3-phenylprop-2-enoate
• CAS: 98748-51-7
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: HMFXOQUFQCVALX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-Chloromethyl-3-phenyl-acrylic acid ethyl ester 在 四丁基溴化铵 octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin 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 ethyl 2-methylene-3-phenylpentanoate
  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：

  2-(羟基苯基甲基)丙烯酸乙酯 在 盐酸 、 硫酸 作用下， 生成 (Z)-2-Chloromethyl-3-phenyl-acrylic acid ethyl ester
  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

• Metal-free formal carbon–halogen bond insertion: facile syntheses of 3-halo 3,3′-disubstituted oxindoles and spirooxindole-γ-butyrolactones
  作者：Rong Zhou、Rongfang Liu、Kai Zhang、Ling Han、Honghui Zhang、Wenchao Gao、Ruifeng Li

  DOI：10.1039/c7cc03765a

  日期：——

  A novel P(NMe2)3-mediated formal carbon–halogen bond insertion of isatins into allylic and benzylic bromides/chlorides has been realized, leading to a facile synthesis of 3-halo 3,3′-disubstituted oxindoles. This reaction relies on the unique dual nucleophilic–electrophilic reactivity pattern of the Kukhtin–Ramirez adduct via a cascade SN2–SN2 process. It also represents a rare metal-free approach

  已经实现了一种新型的P（NMe 2）3介导的靛红向烯丙基和苄基溴化物/氯化物的碳-卤键正式插入，从而导致了3卤代3,3'-二取代的吲哚的简便合成。该反应依赖于Kukhtin-Ramirez加合物通过级联S N 2–S N 2过程的独特的双亲核-亲电反应性模式。它还代表了一种罕见的不含金属的碳-卤素键插入方法。用三氟乙酸处理后，已从相应的插入产物中有效地制备了螺并吲哚-γ-丁内酯。