2-(dichloromethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide | 1192489-59-0

• 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: 2-(dichloromethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
• CAS: 1192489-59-0
• 化学式: C₁₅H₁₇Cl₂NO
• 分子量: 298.212
• InChiKey: BIPIGEFDKYIGPJ-QFWMXSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 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：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(dichloromethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide 在 水 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以47%的产率得到(3aS,6aR)-3R-hydroxy-2-[(1R)-phenylethyl]-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one
  参考文献：
  名称：

  Features of catalyzed hydration of 2-(dichloromethyl)-N-[(1R)-1-phenylethyl)]cyclopent-3-ene-1-carboxamides

  摘要：

  The hydration of gem-dichloromethyl group in 2-(dichloromethyl)-N-[(1R)-1-phenylethyl)]cyclopent-3-ene-1-carboxamides in aqueous acetonitrile catalyzed by AgNO3, FeCl3 center dot 6H(2)O, PdCl2, and BaO was investigated. The optimum results were obtained at the use of BaO. It was demonstrated, that Pd-catalyzed reactions initiated intermolecular ether formation from the primary hydration products, bicyclic amides.

  DOI：

  10.1134/s107042800905008x
• 作为产物：
  描述：

  7,7-二氯二环[3.2.0]庚-2-烯-6-酮 、 R(+)-alpha-甲基苄胺 以 苯 为溶剂， 反应 4.0h， 以95%的产率得到2-(dichloromethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  Features of catalyzed hydration of 2-(dichloromethyl)-N-[(1R)-1-phenylethyl)]cyclopent-3-ene-1-carboxamides

  摘要：

  The hydration of gem-dichloromethyl group in 2-(dichloromethyl)-N-[(1R)-1-phenylethyl)]cyclopent-3-ene-1-carboxamides in aqueous acetonitrile catalyzed by AgNO3, FeCl3 center dot 6H(2)O, PdCl2, and BaO was investigated. The optimum results were obtained at the use of BaO. It was demonstrated, that Pd-catalyzed reactions initiated intermolecular ether formation from the primary hydration products, bicyclic amides.

  DOI：

  10.1134/s107042800905008x

文献信息

• Simple synthetic protocol for the preparation of enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones
  作者：Airat M. Gimazetdinov、Nikolay S. Vostrikov、Mansur S. Miftakhov

  DOI：10.1016/j.tetasy.2008.04.001

  日期：2008.5

  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.