1-((7R,8aR)-5-(bromomethyl)-7-methyl-3,4,6,7,8,8a-hexahydroquinolin-1(2H)-yl)ethanone | 1202394-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-((7R,8aR)-5-(bromomethyl)-7-methyl-3,4,6,7,8,8a-hexahydroquinolin-1(2H)-yl)ethanone
• 英文别名: 1-[(7R,8aR)-5-(bromomethyl)-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone
• CAS: 1202394-89-5
• 化学式: C₁₃H₂₀BrNO
• 分子量: 286.212
• InChiKey: OAYZBCWGYDBJDF-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((7R,8aR)-5-(bromomethyl)-7-methyl-3,4,6,7,8,8a-hexahydroquinolin-1(2H)-yl)ethanone 、 1-苄基-2,6-哌啶二甲腈 在 N,N-二甲基丙烯基脲 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(2R,6S)-2,6-bis[[(7R,8aR)-1-acetyl-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-5-yl]methyl]-1-benzylpiperidine-2,6-dicarbonitrile
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e
• 作为产物：
  描述：

  1-((7R,8aR)-5-(hydroxymethyl)-7-methyl-3,4,6,7,8,8a-hexahydroquinolin-1(2H)-yl)ethanone 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以76%的产率得到1-((7R,8aR)-5-(bromomethyl)-7-methyl-3,4,6,7,8,8a-hexahydroquinolin-1(2H)-yl)ethanone
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e

文献信息

• Total Synthesis of (−)-Lycoperine A
  作者：Yoshitaka Nakamura、Anthony M. Burke、Shunsuke Kotani、Joseph W. Ziller、Scott D. Rychnovsky

  DOI：10.1021/ol902389e

  日期：2010.1.1

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.