(R)-methyl 2-((3-chlorophenyl)(diethylphosphoryl)methyl)acrylate | 1236226-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-methyl 2-((3-chlorophenyl)(diethylphosphoryl)methyl)acrylate
• 英文别名: methyl 2-[(R)-(3-chlorophenyl)-diethylphosphorylmethyl]prop-2-enoate
• CAS: 1236226-87-1
• 化学式: C₁₅H₂₀ClO₃P
• 分子量: 314.749
• InChiKey: FYCSVRQIRDEHKF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)(3-chlorophenyl)methyl)acrylate 、 diethylphosphine oxide 在 奎尼丁 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以80%的产率得到(R)-methyl 2-((3-chlorophenyl)(diethylphosphoryl)methyl)acrylate
  参考文献：
  名称：

  Base-Accelerated Enantioselective Substitution of Morita−Baylis−Hillman Carbonates with Dialkyl Phosphine Oxides

  摘要：

  A base could accelerate the S(N)2' or S(N)2' S(N)2' reaction of Morita-Baylis-Hillman (MBH) carbonates with dialkyl phosphine oxides, but the judicial choice of an appropriate base would greatly depress this competitive S(N)2' reaction and allow for a highly enantioselective allylic substitution reaction with satisfactory yields and excellent enantioselectivities.

  DOI：

  10.1021/ol101601d

文献信息

• Base-Accelerated Enantioselective Substitution of Morita−Baylis−Hillman Carbonates with Dialkyl Phosphine Oxides
  作者：Wangsheng Sun、Liang Hong、Chunxia Liu、Rui Wang

  DOI：10.1021/ol101601d

  日期：2010.9.3

  A base could accelerate the S(N)2' or S(N)2' S(N)2' reaction of Morita-Baylis-Hillman (MBH) carbonates with dialkyl phosphine oxides, but the judicial choice of an appropriate base would greatly depress this competitive S(N)2' reaction and allow for a highly enantioselective allylic substitution reaction with satisfactory yields and excellent enantioselectivities.