(5R,6S,3E)-methyl 5-methyl-6-(N-methylcarbamate)-6-(4-chlorophenyl)hexenoate

• 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: (5R,6S,3E)-methyl 5-methyl-6-(N-methylcarbamate)-6-(4-chlorophenyl)hexenoate
• 英文别名: methyl (E,5R,6S)-6-(4-chlorophenyl)-6-(methoxycarbonylamino)-5-methylhex-3-enoate
• 化学式: C₁₆H₂₀ClNO₄
• 分子量: 325.792
• InChiKey: SRMGIUOPHQBESE-MHRJHOKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 (E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate 、 氨基甲酸甲酯 在 polystyrene-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以77%的产率得到(5R,6S,3E)-methyl 5-methyl-6-(N-methylcarbamate)-6-(4-chlorophenyl)hexenoate
  参考文献：
  名称：

  Three-Component, Room Temperature Crotylation Catalyzed by Solid-Supported Brønsted Acid:  Enantioselective Synthesis of Homoallylic Carbamates

  摘要：

  A heterogeneous, three-component crotylation of in situ generated N-acyl iminium ions has been developed. This reaction proceeds under ambient temperature in MeCN and is catalyzed by macroporous polystyrene-bound sulfonic acid (MP-TsOH). Workup is accomplished by filtration, upon which the catalyst is recoverable. A range of homoallylic amine equivalents have been prepared from the corresponding aldehydes, carbamates, and chiral (E)-crotylsilanes in a highly stereoselective manner.

  DOI：

  10.1021/ol051885s

文献信息

• Three-Component, Room Temperature Crotylation Catalyzed by Solid-Supported Brønsted Acid:  Enantioselective Synthesis of Homoallylic Carbamates
  作者：Darren J. Lipomi、James S. Panek

  DOI：10.1021/ol051885s

  日期：2005.10.1

  A heterogeneous, three-component crotylation of in situ generated N-acyl iminium ions has been developed. This reaction proceeds under ambient temperature in MeCN and is catalyzed by macroporous polystyrene-bound sulfonic acid (MP-TsOH). Workup is accomplished by filtration, upon which the catalyst is recoverable. A range of homoallylic amine equivalents have been prepared from the corresponding aldehydes, carbamates, and chiral (E)-crotylsilanes in a highly stereoselective manner.