(1S,2R)-2-(dichloromethyl)-N-[(1S)-1-phenylethyl]-cyclopent-3-ene-1-carboxamide | 1040919-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2R)-2-(dichloromethyl)-N-[(1S)-1-phenylethyl]-cyclopent-3-ene-1-carboxamide
• 英文别名: (1S,2R)-2-(dichloromethyl)-N-[(1S)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
• CAS: 1040919-28-5
• 化学式: C₁₅H₁₇Cl₂NO
• 分子量: 298.212
• InChiKey: BIPIGEFDKYIGPJ-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 以 苯 为溶剂， 反应 3.5h， 生成 (1S,2R)-2-(dichloromethyl)-N-[(1S)-1-phenylethyl]-cyclopent-3-ene-1-carboxamide 、 (1R,2S)-2-(dichloromethyl)-N-[(1S)-1-phenylethyl]-cyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  Simple synthetic protocol for the preparation of enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones

  摘要：

  Diastereomeric amides produced via the decomposition of easily available (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one by treatment with (+)- or (-)-alpha-methylbenzylamines were transformed into bicyclic lactam-aminals, which can easily be separated using the column chromatography on SiO2. The latter products lead to enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones after the removal of the chiral auxiliary. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.001