(Z)-2-phenyl-1-[2-(phenylsulfanyl)phenyl]-1-ethanone oxime | 313513-79-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-2-phenyl-1-[2-(phenylsulfanyl)phenyl]-1-ethanone oxime
• 英文别名: (NZ)-N-[2-phenyl-1-(2-phenylsulfanylphenyl)ethylidene]hydroxylamine
• CAS: 313513-79-0
• 化学式: C₂₀H₁₇NOS
• 分子量: 319.427
• InChiKey: ZMADFTRASSPMFA-VZCXRCSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙酸叔丁酯 、 (Z)-2-phenyl-1-[2-(phenylsulfanyl)phenyl]-1-ethanone oxime 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以80%的产率得到tert-butyl (Z)-2-[({phenyl[2-(phenylsulfanyl)phenyl]ethylidene}amino)oxy]acetate
  参考文献：
  名称：

  Stereomutation of the Enantiomers of HinderedO-Substituted Oximes

  摘要：

  As anticipated by Molecular Mechanics calculations, the (E) and (Z) isomers of diaryl ketone oximes containing a bulky substituent (PhS or Ph2N) in the ortho position of the phenyl ring, display different conformational preferences. Whereas the (E) isomers exhibit a plane of symmetry at any accessible temperature, the (Z) isomers exist as a pair of stereolabile enantiomers that were detected by low-temperature NMR spectroscopy in a chiral environment. In a number of O-substituted oximes, the enantiomerisation barriers of the (Z) isomers were determined by monitoring the line shape of the NMR signals of diastereotopic methylene hydrogen atoms as a function of temperature. The four stereoisomers, generated by the combination of the conformational axial chirality with the configurationally stable chirality of a stereogenic centre, have been all detected in a specifically substituted oxime and monitored in an appropriate chiral environment. The NMR results in solution were confirmed by X-ray diffraction measurements in the solid state.

  DOI：

  10.1002/1099-0690(200010)2000:20<3439::aid-ejoc3439>3.0.co;2-j
• 作为产物：
  描述：

  邻氯苯基苄基酮 在 吡啶 、 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 (Z)-2-phenyl-1-[2-(phenylsulfanyl)phenyl]-1-ethanone oxime
  参考文献：
  名称：

  Stereomutation of the Enantiomers of HinderedO-Substituted Oximes

  摘要：

  As anticipated by Molecular Mechanics calculations, the (E) and (Z) isomers of diaryl ketone oximes containing a bulky substituent (PhS or Ph2N) in the ortho position of the phenyl ring, display different conformational preferences. Whereas the (E) isomers exhibit a plane of symmetry at any accessible temperature, the (Z) isomers exist as a pair of stereolabile enantiomers that were detected by low-temperature NMR spectroscopy in a chiral environment. In a number of O-substituted oximes, the enantiomerisation barriers of the (Z) isomers were determined by monitoring the line shape of the NMR signals of diastereotopic methylene hydrogen atoms as a function of temperature. The four stereoisomers, generated by the combination of the conformational axial chirality with the configurationally stable chirality of a stereogenic centre, have been all detected in a specifically substituted oxime and monitored in an appropriate chiral environment. The NMR results in solution were confirmed by X-ray diffraction measurements in the solid state.

  DOI：

  10.1002/1099-0690(200010)2000:20<3439::aid-ejoc3439>3.0.co;2-j

文献信息

• Stereomutation of the Enantiomers of HinderedO-Substituted Oximes
  作者：Rino Leardini、Lodovico Lunazzi、Andrea Mazzanti、Hamish McNab、Daniele Nanni

  DOI：10.1002/1099-0690(200010)2000:20<3439::aid-ejoc3439>3.0.co;2-j

  日期：2000.10

  As anticipated by Molecular Mechanics calculations, the (E) and (Z) isomers of diaryl ketone oximes containing a bulky substituent (PhS or Ph2N) in the ortho position of the phenyl ring, display different conformational preferences. Whereas the (E) isomers exhibit a plane of symmetry at any accessible temperature, the (Z) isomers exist as a pair of stereolabile enantiomers that were detected by low-temperature NMR spectroscopy in a chiral environment. In a number of O-substituted oximes, the enantiomerisation barriers of the (Z) isomers were determined by monitoring the line shape of the NMR signals of diastereotopic methylene hydrogen atoms as a function of temperature. The four stereoisomers, generated by the combination of the conformational axial chirality with the configurationally stable chirality of a stereogenic centre, have been all detected in a specifically substituted oxime and monitored in an appropriate chiral environment. The NMR results in solution were confirmed by X-ray diffraction measurements in the solid state.