3,3-Dichloro-4-(chloromethyl)-5-methyl-5-(4-methylpent-3-enyl)pyrrolidin-2-one | 138816-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3,3-Dichloro-4-(chloromethyl)-5-methyl-5-(4-methylpent-3-enyl)pyrrolidin-2-one
• CAS: 138816-26-9
• 化学式: C₁₂H₁₈Cl₃NO
• 分子量: 298.64
• InChiKey: JQCJGLACVGUVPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-Dichloro-4-(chloromethyl)-5-methyl-5-(4-methylpent-3-enyl)pyrrolidin-2-one 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 xylene 为溶剂， 反应 6.0h， 以54%的产率得到6-氮杂二环[3.2.1]辛烷-7-酮,1-氯-8-(氯甲基)-5-甲基-2-(1-甲基乙烯基)-
  参考文献：
  名称：

  Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

  摘要：

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

  DOI：

  10.1021/jo00032a016
• 作为产物：
  描述：

  2,2,2-三氯-n-(1,5-二甲基-1-乙烯基-4-己烯)乙酰胺 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 xylene 为溶剂， 反应 2.0h， 以3%的产率得到3,3-Dichloro-4-(chloromethyl)-5-methyl-5-(4-methylpent-3-enyl)pyrrolidin-2-one
  参考文献：
  名称：

  Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

  摘要：

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

  DOI：

  10.1021/jo00032a016

文献信息

• Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides
  作者：Hideo Nagashima、Hidetoshi Wakamatsu、Nobuyasu Ozaki、Tsutomu Ishii、Masakazu Watanabe、Tomonori Tajima、Kenji Itoh

  DOI：10.1021/jo00032a016

  日期：1992.3

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.