10-benzyl-6,7,8,9,9a,10-hexahydro-1H-pyrazolo[4,3-b]phenazin-5(5aH)-ylacetonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 10-benzyl-6,7,8,9,9a,10-hexahydro-1H-pyrazolo[4,3-b]phenazin-5(5aH)-ylacetonitrile
• 英文别名: 2-[(5aS,9aR)-10-benzyl-5a,6,7,8,9,9a-hexahydro-1H-pyrazolo[3,4-b]phenazin-5-yl]acetonitrile
• 化学式: C₂₂H₂₃N₅
• 分子量: 357.458
• InChiKey: IZESWFOJPIULBX-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-环己二酮 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 28.0h， 生成 10-benzyl-6,7,8,9,9a,10-hexahydro-1H-pyrazolo[4,3-b]phenazin-5(5aH)-ylacetonitrile
  参考文献：
  名称：

  Regioselective synthesis of novel substituted indazole-5,6-diamine derivatives

  摘要：

  The synthesis of a series of novel indazole-5,6-diamine derivatives is described. This indazole ring system was incorporated in an octahydropyrrolo[3,4-b]phenazine scaffold and was diversely and regioselectively substituted on the nitrogen atoms at the 5- and 10-positions. Thus, the nitrogen atom at the 5-position was found to be more reactive toward electrophiles than the one at the 10-position. This difference of reactivity could be attributed to the electronic effect of the pyrazole moiety. Moreover, an unexpected tetrahydropyran protecting group migration was observed from the N-1 atom to the C-11 position of the octahydropyrrolo[3.4-b]phenazine scaffold. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.010

文献信息

• Regioselective synthesis of novel substituted indazole-5,6-diamine derivatives
  作者：Laurent Gavara、Emmanuelle Saugues、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.tet.2011.01.010

  日期：2011.3

  The synthesis of a series of novel indazole-5,6-diamine derivatives is described. This indazole ring system was incorporated in an octahydropyrrolo[3,4-b]phenazine scaffold and was diversely and regioselectively substituted on the nitrogen atoms at the 5- and 10-positions. Thus, the nitrogen atom at the 5-position was found to be more reactive toward electrophiles than the one at the 10-position. This difference of reactivity could be attributed to the electronic effect of the pyrazole moiety. Moreover, an unexpected tetrahydropyran protecting group migration was observed from the N-1 atom to the C-11 position of the octahydropyrrolo[3.4-b]phenazine scaffold. (C) 2011 Elsevier Ltd. All rights reserved.