7,8-dimethoxy-1-m-tolyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 1080523-54-1

• 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: 7,8-dimethoxy-1-m-tolyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• 英文别名: 7,8-dimethoxy-5-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 1080523-54-1
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: ZULQWNBVGTWJJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxy-1-m-tolyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 在 iron(III) chloride hexahydrate 作用下， 以 硝基苯 为溶剂， 反应 10.0h， 以53%的产率得到6,7-dimethoxy-1-(3-methylphenyl)-3,4-dihydroisoquinoline
  参考文献：
  名称：

  前所未有的FeCl3⋅6H2O促进1-芳基-2,3,4,5-四氢-1H-3苯并ze庚因骨架重排：合成C1四元四氢异喹啉的新策略

  摘要：

  取代基事项：A骨架的1-芳基-3-苯并吖庚因的重排用的FeCl的2.0当量开发3 ⋅6ħ 2 ö在PHNO 2。该ñ -取代了对产品结构的显着影响。在N-烷基苯并ze庚因的情况下，获得了1-芳基四氢异喹啉，而N-酰基-苯并ze庚因产生了一系列独特的C1季铵基1-芳基-1-甲酰基四氢异喹啉。

  DOI：

  10.1002/chem.200901197

文献信息

• ‘Click’ D1 receptor agonists with a 5-HT1A receptor pharmacophore producing D2 receptor activity
  作者：Jing Zhang、Hai Zhang、Wenxian Cai、Leiping Yu、Xuechu Zhen、Ao Zhang

  DOI：10.1016/j.bmc.2009.06.019

  日期：2009.7

  A series of new 1-aryl-3-benzazepine derivatives containing an arylpiperazinyl function as the N3 substituent were synthesized by combining a D-1 receptor agonistic pharmacophore and a 5-HT1A receptor pharmacophore through Click reaction. Interestingly, these compounds generally do not have good binding affinity at the D-1 receptor, but most compounds are potent at both D-2 and 5-HT1A receptors. Compound 8h, containing 1-m-tolyl-benzazepine scaffold and 2-methoxyphenylpiperazine core, displayed good affinity at all tested receptors, with K-i values of 144, 80, and 133 nM, for the D-1, D-2, and 5-HT1A receptors, respectively. Compound 13 with the triazole moiety formed differently from that in 8h showed the highest affinity at the D-2 receptor with K-i value of 19 nM. This compound also showed moderate affinity at the 5-HT1A (K-i, 105 nM), and D-1 (K-i, 551 nM) receptors. Functional assays indicated that both compounds 13 and 8h are antagonists at D-1 and D-2 receptors, whereas full agonistic activity at the 5-HT1A receptor was observed. In agreement with the binding affinity, compound 13 is a high efficacy D-2 antagonist and 5-HT1A agonist. (C) 2009 Elsevier Ltd. All rights reserved.
• Unprecedented FeCl₃⋅6 H₂O-Promoted Skeleton Rearrangement of 1-Aryl-2,3,4,5-tetrahydro-1<i>H</i>-3-benzazepines: A New Strategy for the Synthesis of C1 Quaternary Tetrahydroisoquinolines
  作者：Jing Zhang、Ao Zhang

  DOI：10.1002/chem.200901197

  日期：2009.10.26

  Substituent matters: A skeleton rearrangement of 1‐aryl‐3‐benzazepines was developed with 2.0 equiv of FeCl3⋅6 H2O in PhNO2. The N‐substituents had a dramatic influence on the structures of the products. In the case of N‐alkylbenzazepines, 1‐aryltetrahydroisoquinolines were obtained, whereas N‐acyl‐benzazepines yielded a series of unique C1 quaternary 1‐aryl‐1‐formyltetrahydroisoquinolines.

  取代基事项：A骨架的1-芳基-3-苯并吖庚因的重排用的FeCl的2.0当量开发3 ⋅6ħ 2 ö在PHNO 2。该ñ -取代了对产品结构的显着影响。在N-烷基苯并ze庚因的情况下，获得了1-芳基四氢异喹啉，而N-酰基-苯并ze庚因产生了一系列独特的C1季铵基1-芳基-1-甲酰基四氢异喹啉。