(9-fluoro-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)(piperidin-1-yl)methanone | 1239017-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (9-fluoro-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)(piperidin-1-yl)methanone
• 英文别名: (6-Fluoro-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7-trien-10-yl)-piperidin-1-ylmethanone
• CAS: 1239017-85-6
• 化学式: C₁₇H₂₂FN₃O
• 分子量: 303.38
• InChiKey: WDOWHGBYXBRODN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9-fluoro-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)(piperidin-1-yl)methanone 在 palladium 10% on activated carbon 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 环己烯 为溶剂， 以72%的产率得到(9-fluoro-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Pictet−Spengler Based Synthesis of a Bisarylmaleimide Glycogen Synthase Kinase-3 Inhibitor

  摘要：

  A practical synthesis of the glycogen synthase kinase-3 (GSK3) inhibitor bisarylmaleimide 1 has been accomplished employing Pictet-Spengler methodology to access the indole 7-position in preparing the benzodiazepine tricyclic fragment. A seven-step linear sequence that starts with commercially available 5-fluoroindole 7 affords the bisarylmaleimide 1 in 33% overall yield.

  DOI：

  10.1021/ol101405g
• 作为产物：
  描述：

  9-fluoro-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole 、 1-哌啶酰氯 在 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 (9-fluoro-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Pictet−Spengler Based Synthesis of a Bisarylmaleimide Glycogen Synthase Kinase-3 Inhibitor

  摘要：

  A practical synthesis of the glycogen synthase kinase-3 (GSK3) inhibitor bisarylmaleimide 1 has been accomplished employing Pictet-Spengler methodology to access the indole 7-position in preparing the benzodiazepine tricyclic fragment. A seven-step linear sequence that starts with commercially available 5-fluoroindole 7 affords the bisarylmaleimide 1 in 33% overall yield.

  DOI：

  10.1021/ol101405g