2-((1S,2R,5R)-2-(3-azidopropyl)-5-methyl-3-oxocyclohexyl)-acetonitrile | 1438285-32-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-((1S,2R,5R)-2-(3-azidopropyl)-5-methyl-3-oxocyclohexyl)-acetonitrile
• 英文别名: 2-[(1S,2R,5R)-2-(3-azidopropyl)-5-methyl-3-oxocyclohexyl]acetonitrile
• CAS: 1438285-32-5
• 化学式: C₁₂H₁₈N₄O
• 分子量: 234.301
• InChiKey: UZONIDCLMMHPRO-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  长叶薄荷酮 在 正丁基锂 、 sodium azide 、 水 、 sodium hydride 、 二异丙胺 、 间氯过氧苯甲酸 、 sodium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 108.0h， 生成 2-((1S,2R,5R)-2-(3-azidopropyl)-5-methyl-3-oxocyclohexyl)-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

• 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.