N-benzyl-3-chloro-N-(cyclopent-1-en-1-yl)isonicotinamide | 1429043-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyl-3-chloro-N-(cyclopent-1-en-1-yl)isonicotinamide
• CAS: 1429043-81-1
• 化学式: C₁₈H₁₇ClN₂O
• 分子量: 312.799
• InChiKey: UEJQEVXFHPZCFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.2
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-chloro-N-(cyclopent-1-en-1-yl)isonicotinamide 、 氯甲酸甲酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 methyl-1-benzyl-3'-chloro-6a-hydroxy-2-oxo-2,3a,4,5,6,6a-hexahydro-1H,1'H-spiro[cyclopenta[b]pyrrole-3,4'-pyridine]-1'-carboxylate 、 methyl-1-benzyl-3'-chloro-6a-hydroxy-2-oxo-2,3a,4,5,6,6a-hexahydro-1H,1'H-spiro[cyclopenta[b]pyrrole-3,4'-pyridine]-1'-carboxylate
  参考文献：
  名称：

  Spirocyclic Dihydropyridines by Electrophile-Induced Dearomatizing Cyclization of N-Alkenyl Pyridinecarboxamides

  摘要：

  On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

  DOI：

  10.1021/ol400571j
• 作为产物：
  描述：

  苄胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 生成 N-benzyl-3-chloro-N-(cyclopent-1-en-1-yl)isonicotinamide
  参考文献：
  名称：

  Spirocyclic Dihydropyridines by Electrophile-Induced Dearomatizing Cyclization of N-Alkenyl Pyridinecarboxamides

  摘要：

  On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

  DOI：

  10.1021/ol400571j