9-fluoro-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole | 1239017-82-3

• 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-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole
• 英文别名: 6-Fluoro-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7-triene
• CAS: 1239017-82-3
• 化学式: C₁₁H₁₃FN₂
• 分子量: 192.236
• InChiKey: VSUKFTYDWQMAPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(5-fluoroindolin-1-yl)ethanamine acetate 在 聚合甲醛 、 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 9-fluoro-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole
  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

文献信息

• Pictet−Spengler Based Synthesis of a Bisarylmaleimide Glycogen Synthase Kinase-3 Inhibitor
  作者：Nicholas A. Magnus、Christopher P. Ley、Patrick M. Pollock、James P. Wepsiec

  DOI：10.1021/ol101405g

  日期：2010.8.20

  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.