(5S,6aR,10aR)-Decahydro-dipyrrolo[1,2-a;1',2'-c]pyrimidine-5-carbonitrile | 178625-91-7

• 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: (5S,6aR,10aR)-Decahydro-dipyrrolo[1,2-a;1',2'-c]pyrimidine-5-carbonitrile
• 英文别名: (2R,7S,9R)-1,6-diazatricyclo[7.3.0.02,6]dodecane-7-carbonitrile
• CAS: 178625-91-7
• 化学式: C₁₁H₁₇N₃
• 分子量: 191.276
• InChiKey: QMUTUEDVCVMMBO-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (5S,6aR,10aR)-Decahydro-dipyrrolo[1,2-a;1',2'-c]pyrimidine-5-carbonitrile 在 六甲基磷酰三胺 、 氨 、 sodium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 (+)-tetraponerine-2
  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：

  (3R,7aS)-5-(2,2-diethoxyethyl)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazole-5-carbonitrile 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.67h， 生成 (5S,6aR,10aR)-Decahydro-dipyrrolo[1,2-a;1',2'-c]pyrimidine-5-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.