methyl (4S)-4-cyano-4-(3,4-dichlorophenyl)-6-(3-morpholin-4-ylazetidin-1-yl)hexanoate | 303728-39-4

• 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: methyl (4S)-4-cyano-4-(3,4-dichlorophenyl)-6-(3-morpholin-4-ylazetidin-1-yl)hexanoate
• CAS: 303728-39-4
• 化学式: C₂₁H₂₇Cl₂N₃O₃
• 分子量: 440.37
• InChiKey: LHVXYGZGSBQXDJ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4S)-4-cyano-4-(3,4-dichlorophenyl)-6-(3-morpholin-4-ylazetidin-1-yl)hexanoate 在 镍 ammonium hydroxide 、 18-冠醚-6 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 (5S)-5-(3,4-dichlorophenyl)-1-[(3-methoxyphenyl)methyl]-5-[2-(3-morpholin-4-ylazetidin-1-yl)ethyl]piperidin-2-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of a tachykinin NK-2 antagonist

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00796-7
• 作为产物：
  描述：

  4-氰-4-(3,4-二氯苯)环己酮 在 对甲苯磺酸 、 臭氧 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (4S)-4-cyano-4-(3,4-dichlorophenyl)-6-(3-morpholin-4-ylazetidin-1-yl)hexanoate
  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