4-(3,4-dichlorophenyl)-1-methyl-piperidin-4-yl-methanol | 672926-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(3,4-dichlorophenyl)-1-methyl-piperidin-4-yl-methanol
• 英文别名: 1-N-methyl-4-hydroxymethyl-4-(3,4-dichlorophenyl)piperidine；[4-(3,4-dichlorophenyl)-1-methylpiperidin-4-yl]methanol
• CAS: 672926-66-8
• 化学式: C₁₃H₁₇Cl₂NO
• 分子量: 274.19
• InChiKey: XAGJIICFOBTYKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3,4-dichlorophenyl)-1-methyl-piperidin-4-yl-methanol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到4-(3,4-Dichloro-phenyl)-1-methyl-piperidine-4-carbaldehyde
  参考文献：
  名称：

  Structure–activity studies of 3′-4′-dichloro-meperidine analogues at dopamine and serotonin transporters

  摘要：

  The structure-activity relationships of 3',4'-dichloro-meperidine were investigated at dopamine (DAT) and serotonin transporters (SERT). Large ester substituents and lipophilic groups at the 4-position favored molecular recognition at the SERT. The benzyl ester of 3',4'-dichloro-meperidine exhibited high potency and high selectivity for the SERT (DAT/SERT = 760). Chemical modification of the ester group and N-substitution generally led to compounds with decreased DAT affinity. Only small esters and alkyl groups were tolerated at the 4-position of the meperidine ring system by the DAT. Overall, the meperidine analogues were generally more selective for the SERT than for the DAT. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.025
• 作为产物：
  描述：

  4-(3,4-dichlorophenyl)-1-methylpiperidine-4-carboxylic acid ethyl ester 在 三乙基硼氢化锂 、 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 19.0h， 生成 4-(3,4-dichlorophenyl)-1-methyl-piperidin-4-yl-methanol
  参考文献：
  名称：

  [EN] NAPHTHYL ETHER COMPOUNDS AND THEIR USE
  [FR] COMPOSES DE NAPHTYL ETHER ET LEUR UTILISATION

  摘要：

  具有以下结构的化合物，其中R1、R2、R3、R4、R5、R6、R7、m和n如规范中定义，其体内可水解的前体，其药用盐，以及在治疗中的使用、制药组合物和使用相同的治疗方法。

  公开号：

  WO2004022539A1

文献信息

• [EN] NAPHTHYL ETHER COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES DE NAPHTYL ETHER ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004022539A1

  公开（公告）日：2004-03-18

  Compounds having the following structure wherein R1, R2, R3, R4, R5, R6, R7 m and n are as defined in the specification, in vivo-hydrolysable precursors thereof, pharmaceutically-acceptable salts thereof, the use in therapy and pharmaceutical compositions and methods of treatment using the same.

  具有以下结构的化合物，其中R1、R2、R3、R4、R5、R6、R7、m和n如规范中定义，其体内可水解的前体，其药用盐，以及在治疗中的使用、制药组合物和使用相同的治疗方法。
• Naphthyl ether compounds and their use
  申请人：Bernstein Peter

  公开号：US20050245572A1

  公开（公告）日：2005-11-03

  Compounds having the following structure wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 m and n are as defined in the specification, in vivo-hydrolysable precursors thereof, pharmaceutically-acceptable salts thereof, the use in therapy and pharmaceutical compositions and methods of treatment using the same.

  具有以下结构的化合物，其中R1、R2、R3、R4、R5、R6、R7m和n如规范中所定义，其体内可水解的前体物，其药学上可接受的盐，其在治疗中的应用以及使用其进行治疗的制药组合物和方法。
• NAPHTHYL ETHER COMPOUNDS AND THEIR USE
  申请人：AstraZeneca AB

  公开号：EP1546101A1

  公开（公告）日：2005-06-29
• Structure–activity studies of 3′-4′-dichloro-meperidine analogues at dopamine and serotonin transporters
  作者：Jill B. Rhoden、Maud Bouvet、Sari Izenwasser、Dean Wade、Stacey A. Lomenzo、Mark L. Trudell

  DOI：10.1016/j.bmc.2005.05.025

  日期：2005.10

  The structure-activity relationships of 3',4'-dichloro-meperidine were investigated at dopamine (DAT) and serotonin transporters (SERT). Large ester substituents and lipophilic groups at the 4-position favored molecular recognition at the SERT. The benzyl ester of 3',4'-dichloro-meperidine exhibited high potency and high selectivity for the SERT (DAT/SERT = 760). Chemical modification of the ester group and N-substitution generally led to compounds with decreased DAT affinity. Only small esters and alkyl groups were tolerated at the 4-position of the meperidine ring system by the DAT. Overall, the meperidine analogues were generally more selective for the SERT than for the DAT. (c) 2005 Elsevier Ltd. All rights reserved.