(4aR,5R,7S,8aS)-5-(cyanomethyl)-8a-ethynyl-N,N,7-trimethyloctahydroquinoline-1(2H)-carboxamide | 1438285-79-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4aR,5R,7S,8aS)-5-(cyanomethyl)-8a-ethynyl-N,N,7-trimethyloctahydroquinoline-1(2H)-carboxamide
• CAS: 1438285-79-0
• 化学式: C₁₇H₂₅N₃O
• 分子量: 287.405
• InChiKey: ROFCRXKATPSKPY-KCYZZUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  47.34
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 、 (4aR,5R,7S,8aS)-5-(cyanomethyl)-8a-ethynyl-N,N,7-trimethyloctahydroquinoline-1(2H)-carboxamide 在 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以22%的产率得到(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-benzyl-N,N,16,16′-tetramethyl-10′-(trimethylsilyl)-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,-16′,17,17′-octadecahydro[10,11′-bi(5,10bpropano-1,7-phenanthroline)]-1′(15′H)carboxamide
  参考文献：
  名称：

  Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

  摘要：

  The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycocline core.

  DOI：

  10.1021/jo400695c
• 作为产物：
  描述：

  长叶薄荷酮 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 ammonium cerium (IV) nitrate 、 magnesium(II) perchlorate 、 水 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 copper(l) chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 112.09h， 生成 (4aR,5R,7S,8aS)-5-(cyanomethyl)-8a-ethynyl-N,N,7-trimethyloctahydroquinoline-1(2H)-carboxamide
  参考文献：
  名称：

  Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

  摘要：

  The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycocline core.

  DOI：

  10.1021/jo400695c