(2R,7S,9R)-7-pentyl-1,6-diazatricyclo[7.3.0.02,6]dodecane-7-carbonitrile | 178739-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2R,7S,9R)-7-pentyl-1,6-diazatricyclo[7.3.0.02,6]dodecane-7-carbonitrile
• CAS: 178739-94-1
• 化学式: C₁₆H₂₇N₃
• 分子量: 261.41
• InChiKey: LZQBNQVZUFPBAA-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 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-pentyl-1,6-diazatricyclo[7.3.0.02,6]dodecane-7-carbonitrile 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以75%的产率得到(5S,6aR,10aS)-5-pentyldecahydrodipyrrolo[1,2-a:1′,2′-c]pyrimidine
  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：

  (2R)-2-(2,2-diethoxyethyl)pyrrolidine 在 盐酸 、 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 反应 3.0h， 生成 (2R,7S,9R)-7-pentyl-1,6-diazatricyclo[7.3.0.02,6]dodecane-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.