(-)-(S)-5-methyl-3-[(3-phenyl-allyloxycarbonylamino)methyl]-hexanoic acid 3-phenyl-allyl ester

• 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: (-)-(S)-5-methyl-3-[(3-phenyl-allyloxycarbonylamino)methyl]-hexanoic acid 3-phenyl-allyl ester
• 英文别名: [(E)-3-phenylprop-2-enyl] (3S)-5-methyl-3-[[[(E)-3-phenylprop-2-enoxy]carbonylamino]methyl]hexanoate
• 化学式: C₂₇H₃₃NO₄
• 分子量: 435.563
• InChiKey: AUOAWCYQKQEQBP-UUSNCWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(S)-5-methyl-3-[(3-phenyl-allyloxycarbonylamino)methyl]-hexanoic acid 3-phenyl-allyl ester 在 palladium diacetate 吗啉 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以6.0 g的产率得到普瑞巴林
  参考文献：
  名称：

  An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride

  摘要：

  A highly enantioselective synthesis of (S)-3-aminomethyl-5-methylhexanoic acid 1 (Pregabalin) is reported. The key step of the synthesis is a quinine-mediated ring opening of 3-isobutylglutaric anhydride with cinnarryl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.014
• 作为产物：
  描述：

  3-异丁基戊二酸酐 在 二苯基膦叠氮化物 、 三乙胺 、 奎宁 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (-)-(S)-5-methyl-3-[(3-phenyl-allyloxycarbonylamino)methyl]-hexanoic acid 3-phenyl-allyl ester
  参考文献：
  名称：

  An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride

  摘要：

  A highly enantioselective synthesis of (S)-3-aminomethyl-5-methylhexanoic acid 1 (Pregabalin) is reported. The key step of the synthesis is a quinine-mediated ring opening of 3-isobutylglutaric anhydride with cinnarryl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.014

文献信息

• An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride
  作者：Zdenko Hameršak、Irena Stipetić、Amir Avdagić

  DOI：10.1016/j.tetasy.2007.06.014

  日期：2007.7

  A highly enantioselective synthesis of (S)-3-aminomethyl-5-methylhexanoic acid 1 (Pregabalin) is reported. The key step of the synthesis is a quinine-mediated ring opening of 3-isobutylglutaric anhydride with cinnarryl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.