2-(tert-butoxycarbonyl)-3,4,5,6,7,8-hexahydrocyclopentaazepin-1(2H)-one | 132590-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 2-(tert-butoxycarbonyl)-3,4,5,6,7,8-hexahydrocyclopentaazepin-1(2H)-one
• 英文别名: Tert-butyl 1-oxo-3,4,5,6,7,8-hexahydrocyclopenta[c]azepine-2-carboxylate
• CAS: 132590-75-1
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: SHPZAPSWBRHTDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基锂 、 2-(tert-butoxycarbonyl)-3,4,5,6,7,8-hexahydrocyclopentaazepin-1(2H)-one 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-<3-<(tert-butoxycarbonyl)amino>propyl>-2-(2-hydroxyisopropyl)cyclopentene
  参考文献：
  名称：

  A Friedel-Crafts cyclization approach toward cephalotaxine

  摘要：

  The 1-azaspiro[4.4]nonane portion 11 of cephalotaxine was prepared via an intramolecular S(N)2' substitution reaction followed by ozonolysis; condensation of 11 with the aromatic portion 13 gave compound 15; a Friedel-Crafts cyclization of 15 in polyphosphoric acid smoothly afforded the cephalotaxine skeleton 16. A single-crystal X-ray analysis of the HCl salt of 16 confirmed the structure of 16.

  DOI：

  10.1021/jo00008a023
• 作为产物：
  描述：

  3,4,5,6,7,8-hexahydrocyclopentazepin-1(2H)-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以94%的产率得到2-(tert-butoxycarbonyl)-3,4,5,6,7,8-hexahydrocyclopentaazepin-1(2H)-one
  参考文献：
  名称：

  A Friedel-Crafts cyclization approach toward cephalotaxine

  摘要：

  The 1-azaspiro[4.4]nonane portion 11 of cephalotaxine was prepared via an intramolecular S(N)2' substitution reaction followed by ozonolysis; condensation of 11 with the aromatic portion 13 gave compound 15; a Friedel-Crafts cyclization of 15 in polyphosphoric acid smoothly afforded the cephalotaxine skeleton 16. A single-crystal X-ray analysis of the HCl salt of 16 confirmed the structure of 16.

  DOI：

  10.1021/jo00008a023

文献信息

• SHA, CHIN-KANG;YOUNG, JENN-JONG;YEH, CHUN-PONG;CHANG, SHANG-CHIA;WANG, SU+, J. ORG. CHEM., 56,(1991) N, C. 2694-2696
  作者：SHA, CHIN-KANG、YOUNG, JENN-JONG、YEH, CHUN-PONG、CHANG, SHANG-CHIA、WANG, SU+

  DOI：——

  日期：——
• A Friedel-Crafts cyclization approach toward cephalotaxine
  作者：Chin Kang Sha、Jenn Jong Young、Chun Pong Yeh、Shang Chia Chang、Sue Lein Wang

  DOI：10.1021/jo00008a023

  日期：1991.4

  The 1-azaspiro[4.4]nonane portion 11 of cephalotaxine was prepared via an intramolecular S(N)2' substitution reaction followed by ozonolysis; condensation of 11 with the aromatic portion 13 gave compound 15; a Friedel-Crafts cyclization of 15 in polyphosphoric acid smoothly afforded the cephalotaxine skeleton 16. A single-crystal X-ray analysis of the HCl salt of 16 confirmed the structure of 16.