(2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester | 303188-61-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-1-benzoyl-3-(tert-butoxycarbonylmethyl)-4-hydroxypyrrolidine-2-carboxylate；methyl (2S,3R,4S)-1-benzoyl-4-hydroxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pyrrolidine-2-carboxylate
• CAS: 303188-61-6
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: FPPQZKUALGCVDO-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 (2S,3S,4S)-3-carboxymethyl-4-phenylsulfanylpyrolidine-2-carboxylic acid
  参考文献：
  名称：

  由反式-4-羟基-1-脯氨酸合成4-芳基硫烷基取代的类贝氨酸类似物

  摘要：

  哺乳动物中枢神经系统中类胡萝卜素氨基酸的强神经兴奋活性，对作为神经药理学研究工具的新类似物提出了很高的要求。通过（2 S，3 S，4 R）-1-苯甲酰基-3-叔丁氧基羰基甲基-4-甲磺酰基氧基吡咯烷上的许多芳族硫醇盐通过甲磺酸盐置换以平行方式合成了一系列4-芳基硫烷基取代的类胡萝卜素-2-羧酸甲酯9，可从反式-4-羟基-1-脯氨酸5分八个步骤获得。

  DOI：

  10.1016/s0040-4020(01)00770-0
• 作为产物：
  描述：

  (2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  由反式-4-羟基-L-脯氨酸合成4-芳基硫烷基取代的类海因类似物。

  摘要：

  哺乳动物中枢神经系统中类胡萝卜素氨基酸的强神经兴奋活性，对作为神经药理学研究工具的新类似物提出了很高的要求。通过在（2S，3S，4R）-1-苯甲酰基-3-叔丁氧基羰基甲基-4-甲磺酰氧基上的许多芳族和杂芳族硫醇盐通过甲磺酸酯取代反应以平行方式合成了一系列4-芳基硫烷基取代的类胡萝卜素吡咯烷-2-羧酸甲酯8，可以从反式4-羟基-L-脯氨酸5分八步得到。

  DOI：

  10.1016/s0960-894x(00)00352-8

文献信息

• PYRROLIDINE ANALOGUE FOR PREVENTING NEUROGENIC PAIN AND METHOD FOR PRODUCTION THEREOF
  申请人：Gifu University

  公开号：EP2058301A1

  公开（公告）日：2009-05-13

  [Problems] To provide a pyrrolidine analogue having an inhibitory activity on the induction of allodynia, a method for producing the pyrrolidine analogue, and an agent for preventing a neurogenic pain. [Means for Solving the Problems] A pyrrolidine analogue which is a compound represented by the general formula (I) [wherein HOOC-ϕ represents an aromatic substituent having at least one carboxy group attached to the benzene ring] or a salt or ester of the compound. The compound has a potent inhibitory effect on the induction of allodynia.

  问题 提供一种对异动症诱导具有抑制活性的吡咯烷类似物、一种生产该吡咯烷类似物的方法以及一种预防神经源性疼痛的制剂。 [解决问题的方法］ 一种吡咯烷类似物，它是由通式(I)代表的化合物[其中 HOOC-ϕ 代表在苯环上连接有至少一个羧基的芳香取代基]或该化合物的盐或酯。该化合物对异动症的诱导具有强效抑制作用。
• EP2058301
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of an acromelic acid A analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid A in allodynia induction
  作者：Masakatsu Kanazawa、Kyoji Furuta、Hisashi Doi、Tomoko Mori、Toshiaki Minami、Seiji Ito、Masaaki Suzuki

  DOI：10.1016/j.bmcl.2011.02.018

  日期：2011.4

  A novel C-11-labeled PET (positron emission tomography) tracer, which was designed based on the (phenylthio) pyrrolidine derivative that can competitively block the acromelic acid A-induced allodynia, was synthesized. A protocol in which methylation by palladium-mediated coupling of the boronate derivative with [C-11]CH3I and deprotection of the protected amino acid moiety are successively performed in one-pot within 5 min was established for the synthesis of the tracer. The tracer is potentially useful as a tool to investigate the mode of action of acromelic acid A in the induction of allodynia. (C) 2011 Elsevier Ltd. All rights reserved.
• Pyrrolidine analogue for preventing neurogenic pain and method for production thereof
  申请人：Suzuki Masaaki

  公开号：US20090306407A1

  公开（公告）日：2009-12-10

  [Problems] To provide a pyrrolidine analogue having an inhibitory activity on the induction of allodynia, a method for producing the pyrrolidine analogue, and an agent for preventing a neurogenic pain. [Means for Solving the Problems] A pyrrolidine analogue which is a compound represented by the general formula (I) [wherein HOOC-φ represents an aromatic substituent having at least one carboxy group attached to the benzene ring] or a salt or ester of the compound. The compound has a potent inhibitory effect on the induction of allodynia.
• US7968733B2
  申请人：——

  公开号：US7968733B2

  公开（公告）日：2011-06-28