(2'S,3S)-3-benzoyloxy-N-(2-hydroxy-2-phenylethyl)pyrrolidine | 259184-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2'S,3S)-3-benzoyloxy-N-(2-hydroxy-2-phenylethyl)pyrrolidine
• 英文别名: [(3S)-1-[(2S)-2-hydroxy-2-phenylethyl]pyrrolidin-3-yl] benzoate
• CAS: 259184-51-5
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: KLFNEHHZNHJJDJ-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'S,3S)-3-benzoyloxy-N-(2-hydroxy-2-phenylethyl)pyrrolidine 在 sodium hydroxide 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 16.0h， 生成 CJ-15,161
  参考文献：
  名称：

  Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center

  摘要：

  An efficient four-step sequence has been developed for the synthesis of the kappa-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific inversions at a single aziridinium stereogenic center, which leads to overall retention of stereochemistry, in a single operation. The chemistry is straightforward, practical and amenable to large-scale synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00581-0
• 作为产物：
  描述：

  (S)-环氧苯乙烷 、 (S)-3-benzoyloxypyrrolidine 以 1,2-二氯乙烷 为溶剂， 生成 Benzoic acid (S)-1-((R)-2-hydroxy-1-phenyl-ethyl)-pyrrolidin-3-yl ester 、 (2'S,3S)-3-benzoyloxy-N-(2-hydroxy-2-phenylethyl)pyrrolidine
  参考文献：
  名称：

  Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center

  摘要：

  An efficient four-step sequence has been developed for the synthesis of the kappa-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific inversions at a single aziridinium stereogenic center, which leads to overall retention of stereochemistry, in a single operation. The chemistry is straightforward, practical and amenable to large-scale synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00581-0

文献信息

• Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists
  申请人：Pfizer Inc.

  公开号：US20020161241A1

  公开（公告）日：2002-10-31

  A process of preparing compounds having the formula I: 1 or an optical isomer or racemic or optically active mixture thereof, which are useful as selective kappa-receptor agonists.

  一种制备化合物I：1及其光学异构体或外消旋或光学活性混合物的过程，该化合物是作为选择性kappa-受体激动剂有用的。
• US6624313B2
  申请人：——

  公开号：US6624313B2

  公开（公告）日：2003-09-23