diethylstilbestrol-dimethylsulfoxid adjunct | 35079-22-2

• 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: diethylstilbestrol-dimethylsulfoxid adjunct
• 英文别名: trans-diethylstilbestrol dimethylsulfoxide solvate；Diethylstilbestrol dimethylsulfoxide solvate (1/1)；4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol;methylsulfinylmethane
• CAS: 35079-22-2
• 化学式: C₂H₆OS*C₁₈H₂₀O₂
• 分子量: 346.491
• InChiKey: KTIYTWZCVUZTPT-ZAGWXBKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  己烯雌酚 、 二甲基亚砜 反应 504.0h， 以93%的产率得到diethylstilbestrol-dimethylsulfoxid adjunct
  参考文献：
  名称：

  Isomerization of trans-diethylstilbestrol to pseudo-diethylstilbestrol

  摘要：

  This study reports the formation and isolation of a diethylstibestrol-dimethylsulfoxide (DES-DMSO) adjunct and Z-3, 4-di (p-hydroxyphenyl)-2-hexene (psi-DES) from trans-DES. The presence of psi-DES was indicated by NMR and mass spectrometry and confirmed by direct comparison to a reference sample. High resolution NMR (360 MHz) along with the comparison of the chemical shift values of methine and methyl protons attached to carbon-carbon double bonds in Z and E isomers of 3-substituted-2-pentenes and dienestrol derivatives were used in postulating the Z-stereochemistry for psi-DES. A NMR additive increment method was useful for the comparison of the chemical shift values of methine protons in psi-DES and other literature compounds. Nuclear Overhauser Enhancement (NOE) confirmed the Z-stereochemistry of psi-DES.

  DOI：

  10.1016/0039-128x(81)90057-x