trans-2-ethyl-2,3-diphenyloxirane

• 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: trans-2-ethyl-2,3-diphenyloxirane
• 英文别名: (2S,3S)-2-ethyl-2,3-diphenyloxirane
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: WTVDAZOYXCCQFU-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  o-bromo-trans-stilbene oxide 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 trans-2-ethyl-2,3-diphenyloxirane
  参考文献：
  名称：

  Lithiation and Reactions of Stilbene Oxides:  Synthetic Utility

  摘要：

  The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

  DOI：

  10.1021/ol0485013

文献信息

• Epoxide Formation by Indirect Electroreductive Coupling between Aldehydes or Ketones and Activated<i>gem</i>-Dichloro Compounds
  作者：J. P. Paugam、S. Oudeyer、E. Léonel、J.-Y. Nédélec

  DOI：10.1055/s-2004-815915

  日期：——

  Epoxides are prepared by indirect electroreductive coupling of carbonyl compounds (aldehydes or ketones) and activated gem-dichloro compounds. This process is more efficient with aryl ketones than with aryl aldehydes. Though yields are only moderate, this method offers the valuable advantage of avoiding the use of strong bases or peroxides.

  环氧化物是通过羰基化合物（醛或酮）和活化的偕二氯化合物的间接电还原偶联制备的。这个过程使用芳基酮比使用芳基醛更有效。虽然收率适中，但这种方法提供了避免使用强碱或过氧化物的宝贵优势。
• Lithiation and Reactions of Stilbene Oxides:  Synthetic Utility
  作者：Saverio Florio、Varinder Aggarwal、Antonio Salomone

  DOI：10.1021/ol0485013

  日期：2004.11.1

  The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.