1-pent-4-enyl-1,2,3,4-tetrahydroisoquinoline | 1371664-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-pent-4-enyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 1371664-86-6
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: ITWCBWNUODHVKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate 在 四甲基乙二胺 、 叔丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 1-pent-4-enyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Intramolecular Vinylation of Secondary and Tertiary Organolithiums

  摘要：

  Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N'-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates alpha-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp(2) carbon atom, proceeds by a concerted addition-elimination pathway.

  DOI：

  10.1021/ja301591m

文献信息

• Intramolecular Vinylation of Secondary and Tertiary Organolithiums
  作者：Julien Lefranc、Anne M. Fournier、Gaëlle Mingat、Simon Herbert、Tommaso Marcelli、Jonathan Clayden

  DOI：10.1021/ja301591m

  日期：2012.5.2

  Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N'-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates alpha-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp(2) carbon atom, proceeds by a concerted addition-elimination pathway.