4-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine | 93019-52-4

• 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: 4-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
• 英文别名: 4-tosyl-2,3,4,5-tetrahydro-1Hbenzo[e][1,4]diazepine；4-Tosyl-2,3,4,5-tetrahydro-1H-benzo-1,4-diazepin；4-(4-Methylphenyl)sulfonyl-1,2,3,5-tetrahydro-1,4-benzodiazepine；4-(4-methylphenyl)sulfonyl-1,2,3,5-tetrahydro-1,4-benzodiazepine
• CAS: 93019-52-4
• 化学式: C₁₆H₁₈N₂O₂S
• 分子量: 302.397
• InChiKey: LREXHGAXROOQRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine 在 盐酸 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 2,6-二叔丁基吡啶 、 三叔丁基膦 、 氢碘酸 、 氢气 、 碘 、 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， 30.0~115.0 ℃ 、1.72 MPa 条件下， 反应 66.0h， 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 、 2,3,4,5-tetrahydro-1H-benzodiazepine dihydrochloride 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 3.33h， 以95%的产率得到4-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
  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

• Palladium-Catalyzed Intramolecular CH Difluoroalkylation: Synthesis of Substituted 3,3-Difluoro-2-oxindoles
  作者：Shi-Liang Shi、Stephen L. Buchwald

  DOI：10.1002/anie.201410471

  日期：2015.1.26

  3‐difluoro‐2‐oxindoles through a robust and efficient palladium‐catalyzed CH difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate‐determining step for this process.

  描述了通过稳健而有效的钯催化的CH二氟烷基化反应合成3,3-二氟-2-氧吲哚的方法。该方法从容易制备的起始原料中产生了广泛范围的二氟羟吲哚。使用BrettPhos作为配体对于提高效率至关重要。初步的机理研究表明，氧化添加是该过程的决定速率的步骤。
• 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.