5-(4-methylphenylsulfonyl)-5,6,7,10,11,12-hexahydro-4H-cyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-8-ium iodide | 1442654-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-methylphenylsulfonyl)-5,6,7,10,11,12-hexahydro-4H-cyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-8-ium iodide
• 英文别名: 7-(4-Methylphenyl)sulfonyl-7-aza-10-azoniatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17),10,12(16)-pentaene;iodide；7-(4-methylphenyl)sulfonyl-7-aza-10-azoniatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17),10,12(16)-pentaene;iodide
• CAS: 1442654-20-7
• 化学式: C₂₂H₂₃N₂O₂S*I
• 分子量: 506.407
• InChiKey: WJJZGNINMSQCGI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methylphenylsulfonyl)-5,6,7,10,11,12-hexahydro-4H-cyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-8-ium iodide 在 盐酸 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 2,6-二叔丁基吡啶 、 三叔丁基膦 、 氢气 、 lithium chloride 、 3,4-A']4-二萘基)吗啉 作用下， 以 甲醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 50.0~115.0 ℃ 、1.72 MPa 条件下， 反应 54.0h， 生成 盐酸Vabicaserin
  参考文献：
  名称：

  Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

  摘要：

  An efficient, asymmetric synthesis of the 5-HT2C agonist vabicaserin in four chemical steps and 54% overall yield from commercially available benzodiazepine was achieved. The synthesis was highlighted by a novel oxidative, multicomponent reaction to affect the quinolinium ring assembly in one step followed by an unprecedented asymmetric hydrogenation of a 3,4-substituted quinolinium salt.

  DOI：

  10.1021/ol401029k
• 作为产物：
  描述：

  对甲苯磺酰氯 在 氢碘酸 、 碘 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 15.33h， 生成 5-(4-methylphenylsulfonyl)-5,6,7,10,11,12-hexahydro-4H-cyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-8-ium iodide
  参考文献：
  名称：

  Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

  摘要：

  An efficient, asymmetric synthesis of the 5-HT2C agonist vabicaserin in four chemical steps and 54% overall yield from commercially available benzodiazepine was achieved. The synthesis was highlighted by a novel oxidative, multicomponent reaction to affect the quinolinium ring assembly in one step followed by an unprecedented asymmetric hydrogenation of a 3,4-substituted quinolinium salt.

  DOI：

  10.1021/ol401029k

文献信息

• Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt
  作者：Vladimir Dragan、J. Christopher McWilliams、Ross Miller、Karen Sutherland、John L. Dillon、Michael K. O’Brien

  DOI：10.1021/ol401029k

  日期：2013.6.21

  An efficient, asymmetric synthesis of the 5-HT2C agonist vabicaserin in four chemical steps and 54% overall yield from commercially available benzodiazepine was achieved. The synthesis was highlighted by a novel oxidative, multicomponent reaction to affect the quinolinium ring assembly in one step followed by an unprecedented asymmetric hydrogenation of a 3,4-substituted quinolinium salt.