4-Methyl-1,3,4,7,8,9,10,11-octahydrocyclohepta[a]indolizin-2-one | 1084909-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-Methyl-1,3,4,7,8,9,10,11-octahydrocyclohepta[a]indolizin-2-one
• 英文别名: 4-methyl-1,3,4,7,8,9,10,11-octahydrocyclohepta[a]indolizin-2-one
• CAS: 1084909-82-9
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: QOZPPJNJWKVMRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-((2-ethynylcyclohept-1-en-1-yl)methyl)-4-methylazetidin-2-one 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以70%的产率得到4-Methyl-1,3,4,7,8,9,10,11-octahydrocyclohepta[a]indolizin-2-one
  参考文献：
  名称：

  Au-Catalyzed Synthesis of 5,6-Dihydro-8H-indolizin-7-ones from N-(Pent-2-en-4-ynyl)-β-lactams

  摘要：

  Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.

  DOI：

  10.1021/ol802159v

文献信息

• Au-Catalyzed Synthesis of 5,6-Dihydro-8<i>H</i>-indolizin-7-ones from <i>N</i>-(Pent-2-en-4-ynyl)-β-lactams
  作者：Yu Peng、Meng Yu、Liming Zhang

  DOI：10.1021/ol802159v

  日期：2008.11.20

  Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.