5-cyano-5-(3',4'-dichlorophenyl)-4,5-dihydro-3H-oxepin-2-one | 381670-61-7

• 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: 5-cyano-5-(3',4'-dichlorophenyl)-4,5-dihydro-3H-oxepin-2-one
• 英文别名: 5-(3,4-Dichlorophenyl)-2-oxo-3,4-dihydrooxepine-5-carbonitrile
• CAS: 381670-61-7
• 化学式: C₁₃H₉Cl₂NO₂
• 分子量: 282.126
• InChiKey: QOULHRPYENTTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 5-cyano-5-(3',4'-dichlorophenyl)-4,5-dihydro-3H-oxepin-2-one 在 potassium carbonate 作用下， 以60%的产率得到methyl 4-cyano-4-(3,4-dichlorophenyl)-6-oxo-hexanoate
  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-氰基-4-(3',4'-二氯苯基)环己-1-烯基乙酸酯 在 palladium diacetate 、 disodium hydrogenphosphate 、 allylmethylcarbonate (allyl methyl carbonate) 、 urea hydrogen peroxide 、 三氟乙酸酐 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.5h， 生成 5-cyano-5-(3',4'-dichlorophenyl)-4,5-dihydro-3H-oxepin-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