(3S,4S)-4-Phenyl-1-(phenylsulfonyl)-3-(spiro[2,3-dihydrobenzo[b]thiophene-3,4'-piperidine]-10-ylmethyl)pyrrolidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4S)-4-Phenyl-1-(phenylsulfonyl)-3-(spiro[2,3-dihydrobenzo[b]thiophene-3,4'-piperidine]-10-ylmethyl)pyrrolidine
• 英文别名: 1'-[[(3S,4S)-1-(benzenesulfonyl)-4-phenylpyrrolidin-3-yl]methyl]spiro[2H-1-benzothiophene-3,4'-piperidine]
• 化学式: C₂₉H₃₂N₂O₂S₂
• 分子量: 504.717
• InChiKey: MLGUGUGJZZJNEQ-AZGAKELHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-Phenyl-1-(phenylsulfonyl)-3-(spiro[2,3-dihydrobenzo[b]thiophene-3,4'-piperidine]-10-ylmethyl)pyrrolidine 在 Oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 以73%的产率得到1'-[[(3S,4S)-1-(benzenesulfonyl)-4-phenyl-pyrrolidin-3-yl]methyl]spiro[2H-benzothiophene-3,4'-piperidine] 1-oxide
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements

  摘要：

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00232-3
• 作为产物：
  描述：

  (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 在 palladium dihydroxide lithium aluminium tetrahydride 、 草酰氯 、 TEA 、 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 碳酸氢铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S,4S)-4-Phenyl-1-(phenylsulfonyl)-3-(spiro[2,3-dihydrobenzo[b]thiophene-3,4'-piperidine]-10-ylmethyl)pyrrolidine
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements

  摘要：

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00232-3

文献信息

• 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements
  作者：Jeffrey J. Hale、Richard J. Budhu、Sander G. Mills、Malcolm MacCoss、Lorraine Malkowitz、Salvatore Siciliano、Sandra L. Gould、Julie A. DeMartino、Martin S. Springer

  DOI：10.1016/s0960-894x(01)00232-3

  日期：2001.6

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.