6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine | 461435-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine
• 英文别名: 6-Chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-amine
• CAS: 461435-84-7
• 化学式: C₁₁H₁₅ClN₂
• 分子量: 210.706
• InChiKey: VOLBTTQRFYKISD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 反应 1.0h， 以82%的产率得到6-chloro-7-fluoro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of benzazepine derivatives as 5-HT2C receptor agonists

  摘要：

  To identify potent and selective 5-HT2C receptor agonists, a series of novel benzazepine derivatives were synthesized, and their structure-activity relationships examined. The compounds were evaluated for their 5-HT2C, 5-HT2A, and 5-HT2B receptor binding affinity and intrinsic activity for the 5-HT2C and 5-HT2A receptors. Among these compounds, 6,7-dichloro-2,3,4,5-tetrahydro-1H-3-benzazepine (6) was effective in a rat penile erection model when administered po, which is a symptom of the serotonin syndrome reflecting 5-HT2C receptor activation. Moreover, compound 6 was characterized as a partial agonist of 5-HT2A receptors; therefore, it had little effect on the cardiovascular system. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.009
• 作为产物：
  描述：

  6-chloro-3-methyl-7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine 在 铁粉 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以89%的产率得到6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of benzazepine derivatives as 5-HT2C receptor agonists

  摘要：

  To identify potent and selective 5-HT2C receptor agonists, a series of novel benzazepine derivatives were synthesized, and their structure-activity relationships examined. The compounds were evaluated for their 5-HT2C, 5-HT2A, and 5-HT2B receptor binding affinity and intrinsic activity for the 5-HT2C and 5-HT2A receptors. Among these compounds, 6,7-dichloro-2,3,4,5-tetrahydro-1H-3-benzazepine (6) was effective in a rat penile erection model when administered po, which is a symptom of the serotonin syndrome reflecting 5-HT2C receptor activation. Moreover, compound 6 was characterized as a partial agonist of 5-HT2A receptors; therefore, it had little effect on the cardiovascular system. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.009