(3S,4R)-4-(4-chlorophenyl)-1-methylpiperidine-3-carbonyl chloride | 696660-34-1

• 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: (3S,4R)-4-(4-chlorophenyl)-1-methylpiperidine-3-carbonyl chloride
• CAS: 696660-34-1
• 化学式: C₁₃H₁₅Cl₂NO
• 分子量: 272.174
• InChiKey: DYKXDPJNHALZKV-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(4-chlorophenyl)-1-methylpiperidine-3-carbonyl chloride 在 吡啶 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 生成 (3S,4R)-4-(4-Chloro-phenyl)-3-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-1-methyl-piperidine
  参考文献：
  名称：

  SAR Studies of Piperidine-Based Analogues of Cocaine. Part 3: Oxadiazoles

  摘要：

  The synthesis of novel 4 beta -aryl-1-methyl-3 alpha-(3-substituted-1,2,4-oxadiazol-5-yl)piperidines, bioisosteres of ester (+)-1, is described. The synthesized oxadiazoles were evaluated for their affinity to the DAT and their ability to inhibit monoamine reuptake at the DAT. NET, and 5HTT. The results show that affinity to the DAT and ability to inhibit the reuptake at the DAT, NET, and 5HTT is a function of the size of the substituent in the oxadiazole ring. (+)-(3R,4S)-4 beta-(4-Chlorophenyl)-1-methyl-3 alpha-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine [(+)-2a], which is structurally and pharmacologically most similar to the ester (+)-1 in this series, showed at least a 2-fold longer duration of action when compared to ester (+)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00379-1
• 作为产物：
  描述：

  (3S,4R)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4R)-4-(4-chlorophenyl)-1-methylpiperidine-3-carbonyl chloride
  参考文献：
  名称：

  使用聚合物支持的试剂合成不对称的二价选择性5-羟色胺再摄取抑制剂的简便方法。

  摘要：

  描述了5-羟色胺转运蛋白的不对称二价抑制剂的方便合成。该合成利用聚合物支持的试剂，这些试剂可快速获得新型二价配体，而无需分离或纯化合成中间体。

  DOI：

  10.1016/s0960-894x(00)00576-x

文献信息

• A convenient procedure for the synthesis of nonsymmetrical bivalent selective serotonin reuptake inhibitors using polymer-supported reagents
  作者：Amir P Tamiz、Paola Conti、Mei Zhang、Kenneth M Johnson、Alan P Kozikowski

  DOI：10.1016/s0960-894x(00)00576-x

  日期：2000.12

  A convenient synthesis of nonsymmetrical bivalent inhibitors of the serotonin transporter is described. The synthesis utilizes polymer-supported reagents that allow for rapid access to novel bivalent ligands without the need for isolation or purification of synthetic intermediates.

  描述了5-羟色胺转运蛋白的不对称二价抑制剂的方便合成。该合成利用聚合物支持的试剂，这些试剂可快速获得新型二价配体，而无需分离或纯化合成中间体。
• Application of the Bivalent Ligand Approach to the Design of Novel Dimeric Serotonin Reuptake Inhibitors
  作者：Amir P. Tamiz、Jianrong Zhang、Mei Zhang、Cheng Z. Wang、Kenneth M. Johnson、Alan P. Kozikowski

  DOI：10.1021/ja000199f

  日期：2000.6.1
• SAR Studies of Piperidine-Based Analogues of Cocaine. Part 3: Oxadiazoles
  作者：Pavel A Petukhov、Mei Zhang、Kenneth J Johnson、Srihari R Tella、Alan P Kozikowski

  DOI：10.1016/s0960-894x(01)00379-1

  日期：2001.8

  The synthesis of novel 4 beta -aryl-1-methyl-3 alpha-(3-substituted-1,2,4-oxadiazol-5-yl)piperidines, bioisosteres of ester (+)-1, is described. The synthesized oxadiazoles were evaluated for their affinity to the DAT and their ability to inhibit monoamine reuptake at the DAT. NET, and 5HTT. The results show that affinity to the DAT and ability to inhibit the reuptake at the DAT, NET, and 5HTT is a function of the size of the substituent in the oxadiazole ring. (+)-(3R,4S)-4 beta-(4-Chlorophenyl)-1-methyl-3 alpha-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine [(+)-2a], which is structurally and pharmacologically most similar to the ester (+)-1 in this series, showed at least a 2-fold longer duration of action when compared to ester (+)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.