2-((4aR,5R,7S,8aS)-8a-ethynyl-1-(4-methoxybenzyl)-7-methyldecahydroquinolin-5-yl)acetonitrile | 1225377-97-8

• 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: 2-((4aR,5R,7S,8aS)-8a-ethynyl-1-(4-methoxybenzyl)-7-methyldecahydroquinolin-5-yl)acetonitrile
• 英文别名: 2-[(4aR,5S,7R,8aR)-8a-ethynyl-1-[(4-methoxyphenyl)methyl]-7-methyl-2,3,4,4a,5,6,7,8-octahydroquinolin-5-yl]acetonitrile
• CAS: 1225377-97-8
• 化学式: C₂₂H₂₈N₂O
• 分子量: 336.477
• InChiKey: MFYQDYSNPLTZAD-JHMKDJTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((4aR,5R,7S,8aS)-8a-ethynyl-1-(4-methoxybenzyl)-7-methyldecahydroquinolin-5-yl)acetonitrile 在 ammonium cerium (IV) nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (4aR,5R,7S,8aS)-methyl 5-(Cyanomethyl)-8a-ethynyl-7-methyloctahydroquinoline-1(2H)-carboxylate
  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 、 正丁基锂 、 magnesium(II) perchlorate 、 水 、 sodium hydride 、 potassium carbonate 、 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 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 106.89h， 生成 2-((4aR,5R,7S,8aS)-8a-ethynyl-1-(4-methoxybenzyl)-7-methyldecahydroquinolin-5-yl)acetonitrile
  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

文献信息

• Synthesis of (+)-Complanadine A, an Inducer of Neurotrophic Factor Excretion
  作者：Changxia Yuan、Chih-Tsung Chang、Abram Axelrod、Dionicio Siegel

  DOI：10.1021/ja101956x

  日期：2010.5.5

  A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.
• Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions
  作者：Changxia Yuan、Chih-Tsung Chang、Dionicio Siegel

  DOI：10.1021/jo400695c

  日期：2013.6.7

  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.