(1R,2R)-2-dichloromethyl-5-(1-methylethylidene)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide | 1373312-13-0

• 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: (1R,2R)-2-dichloromethyl-5-(1-methylethylidene)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
• CAS: 1373312-13-0
• 化学式: C₁₈H₂₁Cl₂NO
• 分子量: 338.277
• InChiKey: TXMOQCVUDZVZKN-WQVCFCJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  7,7-Dichloro-4-isopropylidenebicyclo<3.2.0>hept-2-en-6-one 、 (+)-1-phenylethylamine 以 苯 为溶剂， 生成 (1S,2S)-2-dichloromethyl-5-(1-methylethylidene)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide 、 (1R,2R)-2-dichloromethyl-5-(1-methylethylidene)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  Chiral blocks for the synthesis of cyclopentanoids from [2 + 2]-cycloadduct of dichloroketene and dimethylfulvene

  摘要：

  Opening of the alpha,alpha-dichlorocyclobutanone ring in the [2+2]-cycloadduct of dichloroketene and dimethylfulvene with (+)-alpha-methylbenzylamine gave diastereoisomeric 2-dichloromethyl-5-isopropylidene-N-(alpha-methylbenzyl)cyclopent-3-ene-1-carboxamides, and hydrolysis of the latter at the dichloromethyl group afforded the corresponding bicyclic aminals which can be readily separated by chromatography on silica gel. The subsequent removal of the alpha-methylbenzylamine fragment via reduction and hydrolysis resulted in the formation of enantiomerically pure (-)- and (+)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]-furan-1-ones.

  DOI：

  10.1134/s1070428012030190