(1'S,3S,4'R)-(-)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo[2.2.1]heptane-1'-carboxylic acid 3-cyano-3-(3'',4''-dichlorophenyl)-5-methoxycarbonyl-pentanyl 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: (1'S,3S,4'R)-(-)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo[2.2.1]heptane-1'-carboxylic acid 3-cyano-3-(3'',4''-dichlorophenyl)-5-methoxycarbonyl-pentanyl ester
• 英文别名: [(3S)-3-cyano-3-(3,4-dichlorophenyl)-6-methoxy-6-oxohexyl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• 化学式: C₂₄H₂₇Cl₂NO₆
• 分子量: 496.387
• InChiKey: AXTHUSJGIRMRCM-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-(-)-methyl 4-cyano-4-(3',4'-dichlorophenyl)-6-oxo-hexanoate 在 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (1'S,3S,4'R)-(-)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo[2.2.1]heptane-1'-carboxylic acid 3-cyano-3-(3'',4''-dichlorophenyl)-5-methoxycarbonyl-pentanyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of a non-peptide tachykinin NK-2 antagonist

  摘要：

  The synthesis of a tachykinin NK-2 antagonist (S)-11 has been carried out in four steps starting from the the (S)-(+)-enol acetate 3, which was obtained in 100% e.e. by resolution of the racemic eater with Pseudomonas fluorescens lipase. The absolute configuration of the enol acetate (+)-3 was confirmed by X-ray analysis of the camphanyl derivative 13. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01149-7

文献信息

• Chemoenzymatic synthesis of a non-peptide tachykinin NK-2 antagonist
  作者：Andrew J Carnell、Maria Luisa Escudero Hernandez、Alan Pettman、Jamie F Bickley

  DOI：10.1016/s0040-4039(00)01149-7

  日期：2000.8

  The synthesis of a tachykinin NK-2 antagonist (S)-11 has been carried out in four steps starting from the the (S)-(+)-enol acetate 3, which was obtained in 100% e.e. by resolution of the racemic eater with Pseudomonas fluorescens lipase. The absolute configuration of the enol acetate (+)-3 was confirmed by X-ray analysis of the camphanyl derivative 13. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic synthesis of a tachykinin NK-2 antagonist
  作者：Graham Allan、Andrew J Carnell、Maria Luisa Escudero Hernandez、Alan Pettman

  DOI：10.1016/s0040-4020(01)00796-7

  日期：2001.9

  A non-peptide tachykinin antagonist has been synthesized in a short and efficient four step sequence starting from a chiral enol acetate, which was obtained in enantiomerically pure form by resolution using a lipase catalysed transesterification reaction. The biotransformation was optimized in terms of solvent, temperature and immobilization method used. Oxidative cleavage of the (+)-enol acetate to give the key aldehyde ester intermediate could be achieved indirectly by oxidative rearrangement to an enone followed by Baeyer-Villiger oxidation and ring opening, or by epoxidation, rearrangement and oxidative cleavage or most directly by ozonolysis. X-Ray crystallographic analysis of a camphanic ester derivative of an ester alcohol confirmed that the absolute configuration of the enol acetate was (S). (C) 2001 Published by Elsevier Science Ltd.