(2R,7S,9R)-7-propyl-1,6-diazatricyclo[7.4.0.02,6]tridecane-7-carbonitrile | 178625-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (2R,7S,9R)-7-propyl-1,6-diazatricyclo[7.4.0.02,6]tridecane-7-carbonitrile
• CAS: 178625-92-8
• 化学式: C₁₅H₂₅N₃
• 分子量: 247.384
• InChiKey: KDQBLKUUCIWNKD-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,7S,9R)-7-propyl-1,6-diazatricyclo[7.4.0.02,6]tridecane-7-carbonitrile 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以95%的产率得到(+)-tetraponerine-4
  参考文献：
  名称：

  Concise and Stereoselective Syntheses of the Eight Natural Ant Defense Alkaloids (+)-Tetraponerine-1 to (+)-Tetraponerine-8 According to the CN(R,S) Strategy

  摘要：

  The asymmetric syntheses of all the known defense alkaloids of the ant Tetraponera sp. tetraponerines T-1 to T-8 have been accomplished in five or six steps with 20-45% overall yields. The synthesis involved in the cross-condensation of (R)-piperidin-2-ylacetaldehyde with 4-aminobutyraldehyde which upon quenching by cyanide ion gave a stable tricyclic amino nitrile 3 with both a high yield and complete diastereoselectivity. This amino nitrile is the common precursor of four tetraponerines. A similar synthesis using (R)-pyrrolidine-2-ylacetaldehyde provided the tricyclic amino nitrile 2 precursor of the four other tetraponerines.

  DOI：

  10.1021/jo960398a
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 palladium on activated charcoal 盐酸 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 (2R,7S,9R)-7-propyl-1,6-diazatricyclo[7.4.0.02,6]tridecane-7-carbonitrile
  参考文献：
  名称：

  Concise and Stereoselective Syntheses of the Eight Natural Ant Defense Alkaloids (+)-Tetraponerine-1 to (+)-Tetraponerine-8 According to the CN(R,S) Strategy

  摘要：

  The asymmetric syntheses of all the known defense alkaloids of the ant Tetraponera sp. tetraponerines T-1 to T-8 have been accomplished in five or six steps with 20-45% overall yields. The synthesis involved in the cross-condensation of (R)-piperidin-2-ylacetaldehyde with 4-aminobutyraldehyde which upon quenching by cyanide ion gave a stable tricyclic amino nitrile 3 with both a high yield and complete diastereoselectivity. This amino nitrile is the common precursor of four tetraponerines. A similar synthesis using (R)-pyrrolidine-2-ylacetaldehyde provided the tricyclic amino nitrile 2 precursor of the four other tetraponerines.

  DOI：

  10.1021/jo960398a

文献信息

• Concise and Stereoselective Syntheses of the Eight Natural Ant Defense Alkaloids (+)-Tetraponerine-1 to (+)-Tetraponerine-8 According to the CN(<i>R</i>,<i>S</i>) Strategy
  作者：Chongwei Yue、Isabelle Gauthier、Jacques Royer、Henri-Philippe Husson

  DOI：10.1021/jo960398a

  日期：1996.1.1

  The asymmetric syntheses of all the known defense alkaloids of the ant Tetraponera sp. tetraponerines T-1 to T-8 have been accomplished in five or six steps with 20-45% overall yields. The synthesis involved in the cross-condensation of (R)-piperidin-2-ylacetaldehyde with 4-aminobutyraldehyde which upon quenching by cyanide ion gave a stable tricyclic amino nitrile 3 with both a high yield and complete diastereoselectivity. This amino nitrile is the common precursor of four tetraponerines. A similar synthesis using (R)-pyrrolidine-2-ylacetaldehyde provided the tricyclic amino nitrile 2 precursor of the four other tetraponerines.