(9aR,12aS)-5-(4-methylphenylsulfonyl)-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline | 1442654-19-4

• 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: (9aR,12aS)-5-(4-methylphenylsulfonyl)-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline
• 英文别名: (12R,16S)-7-(4-methylphenyl)sulfonyl-7,10-diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene
• CAS: 1442654-19-4
• 化学式: C₂₂H₂₆N₂O₂S
• 分子量: 382.527
• InChiKey: FFPKUEJIBFGZER-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9aR,12aS)-5-(4-methylphenylsulfonyl)-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 16.0h， 以92%的产率得到盐酸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：

  5-(4-methylphenylsulfonyl)-5,6,7,10,11,12-hexahydro-4H-cyclopenta[c][1,4]diazepino[6,7,1-ij]quinolin-8-ium triflate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 2,6-二叔丁基吡啶 、 三叔丁基膦 、 氢气 、 lithium iodide 、 3,4-A']4-二萘基)吗啉 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 50.0 ℃ 、2.07 MPa 条件下， 以78%的产率得到
  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.