1,5-methano-5-methyl-7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine | 135110-36-0

• 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: 1,5-methano-5-methyl-7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine
• 英文别名: 4-Methoxy-1-methyl-9-azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene
• CAS: 135110-36-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: GHRWFKCVVMSXHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-methano-5-methyl-7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine 在 吡啶 、 dimethyl sulfide borane 、 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 Heptyl-carbamic acid 9-ethyl-1-methyl-9-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-trien-4-yl ester
  参考文献：
  名称：

  Syntheses and Anticholinesterase Activity of Tetrahydrobenzazepine Carbamates

  摘要：

  The synthesis of a series of alkylcarbamates of 1,5-methano-2,3,4,5-tetrahydro-1H-2-benzazepin-7-ol is reported. Many of these compounds are potent acetylcholinesterase (AChE) inhibitors. The in vitro AChE inhibition, cholinergic effects, acute toxicity, and elevation of brain acetylcholine levels in vivo of this series of compounds are described, A representative compound, 1d (5,6 mg/kg, po), was able to reverse hemicolinium-3-induced amnesia in the mouse passive avoidance assay.

  DOI：

  10.1021/jm00039a013
• 作为产物：
  描述：

  1,5-methano-3-oxo-5-methyl-7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1,5-methano-5-methyl-7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine
  参考文献：
  名称：

  Syntheses and Anticholinesterase Activity of Tetrahydrobenzazepine Carbamates

  摘要：

  The synthesis of a series of alkylcarbamates of 1,5-methano-2,3,4,5-tetrahydro-1H-2-benzazepin-7-ol is reported. Many of these compounds are potent acetylcholinesterase (AChE) inhibitors. The in vitro AChE inhibition, cholinergic effects, acute toxicity, and elevation of brain acetylcholine levels in vivo of this series of compounds are described, A representative compound, 1d (5,6 mg/kg, po), was able to reverse hemicolinium-3-induced amnesia in the mouse passive avoidance assay.

  DOI：

  10.1021/jm00039a013

文献信息

• Benzazabicyclic carbamates as cholinesterase inhibitors
  申请人：PFIZER INC.

  公开号：EP0415634A2

  公开（公告）日：1991-03-06

  Compounds of the formula I are cholinesterase inhibitors useful in enhancing memory.

  式 I 的化合物 是有助于增强记忆力的胆碱酯酶抑制剂。
• US5387590A
  申请人：——

  公开号：US5387590A

  公开（公告）日：1995-02-07
• US5594002A
  申请人：——

  公开号：US5594002A

  公开（公告）日：1997-01-14
• [EN] BENZAZABICYCLIC CARBAMATES AS NOVEL CHOLINESTERASE INHIBITORS
  申请人：PFIZER INC.

  公开号：WO1991003467A1

  公开（公告）日：1991-03-21

  (EN) Compounds of formula (I), wherein R1, R2, R3, R4, X, m, n, o, p, q and r are as defined below. The compounds are memory enhancing cholinesterase inhibitors useful in enhancing memory, novel intermediates used in their synthesis, and analgesic agents.(FR) L'invention se rapporte à des composés, qui sont représentés par la formule (I), où R1, R2, R3, R4, X, m, n, o, p, q et r sont définis ci-dessous, et qui constituent des inhibiteurs de cholinestérase améliorant la mémoire, ayant un rôle dans l'amélioration des fonctions de la mémoire, à de nouveaux intermédiaires utilisés dans la synthèse de ces composés, ainsi qu'à des agents analgésiques.
• Syntheses and Anticholinesterase Activity of Tetrahydrobenzazepine Carbamates
  作者：Yuhpyng L. Chen、Dane Liston、Jann Nielsen、Douglas Chapin、Audrey Dunaiskis、Kirk Hedberg、Jeffery Ives、Jonathan Jr. Johnson、Shawn Jones

  DOI：10.1021/jm00039a013

  日期：1994.6

  The synthesis of a series of alkylcarbamates of 1,5-methano-2,3,4,5-tetrahydro-1H-2-benzazepin-7-ol is reported. Many of these compounds are potent acetylcholinesterase (AChE) inhibitors. The in vitro AChE inhibition, cholinergic effects, acute toxicity, and elevation of brain acetylcholine levels in vivo of this series of compounds are described, A representative compound, 1d (5,6 mg/kg, po), was able to reverse hemicolinium-3-induced amnesia in the mouse passive avoidance assay.