3,3-Dichloro-4-(chloromethyl)-5,5-dimethylpyrrolidin-2-one | 91989-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3,3-Dichloro-4-(chloromethyl)-5,5-dimethylpyrrolidin-2-one
• CAS: 91989-85-4
• 化学式: C₇H₁₀Cl₃NO
• 分子量: 230.522
• InChiKey: NASWPTWLOODHFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  异戊烯醇 在 tris(triphenylphosphine)ruthenium(II) chloride sodium hydride 作用下， 以 xylene 为溶剂， 反应 2.0h， 生成 3,3-Dichloro-4-(chloromethyl)-5,5-dimethylpyrrolidin-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

• A novel preparative method for γ-butyrolactams via carbon–carbon bond formation: copper or ruthenium-catalysed cyclization of N-allyl trichloroacetamides
  作者：Hideo Nagashima、Hidetoshi Wakamatsu、Kenji Itoh

  DOI：10.1039/c39840000652

  日期：——

  Trichlorinated γ-butyrolactams are formed by copper or ruthenium-catalysed cyclization of Nallyl tichloroacetamides.

  三氯化γ-丁内酰胺是通过铜或钌催化的N烯丙基三氯乙酰胺的环化反应而形成的。
• NAGASHIMA, HIDEO;WAKAMATSU, HIDETOSHI;ITOH, KENJI, J. CHEM. SOC. CHEM. COMMUN., 1984, N 10, 652-653
  作者：NAGASHIMA, HIDEO、WAKAMATSU, HIDETOSHI、ITOH, KENJI

  DOI：——

  日期：——