N-methyl-3-(4-chlorophenyl)-3-(3,4-dichlorophenyl)methoxyazetidine hydrochloride | 1447464-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: N-methyl-3-(4-chlorophenyl)-3-(3,4-dichlorophenyl)methoxyazetidine hydrochloride
• 英文别名: 3-(4-Chlorophenyl)-3-[(3,4-dichlorophenyl)methoxy]-1-methylazetidine;hydrochloride；3-(4-chlorophenyl)-3-[(3,4-dichlorophenyl)methoxy]-1-methylazetidine;hydrochloride
• CAS: 1447464-30-3
• 化学式: C₁₇H₁₆Cl₃NO*ClH
• 分子量: 393.14
• InChiKey: HFLBQUQARDKBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl 3-(4-chlorophenyl)-3-hydroxyazetidine-1-carboxylate 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 N-methyl-3-(4-chlorophenyl)-3-(3,4-dichlorophenyl)methoxyazetidine hydrochloride
  参考文献：
  名称：

  3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters

  摘要：

  A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (K-i = 1.0 nM) and the tetrachloro substituted derivative 7i (K-i = 1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.071

文献信息

• 3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters
  作者：Amber Thaxton、Sari Izenwasser、Dean Wade、Edwin D. Stevens、David L. Mobley、Vivian Jaber、Stacey A. Lomenzo、Mark L. Trudell

  DOI：10.1016/j.bmcl.2013.05.071

  日期：2013.8

  A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (K-i = 1.0 nM) and the tetrachloro substituted derivative 7i (K-i = 1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity. (C) 2013 Elsevier Ltd. All rights reserved.