2-(2,2-二苯基环丙基)环氧乙烷 | 188774-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,2-二苯基环丙基)环氧乙烷
• 英文名称: 1-(2,2-Diphenylcyclopropyl)-1,2-epoxyethane
• 英文别名: 2-(2,2-Diphenylcyclopropyl)oxirane；2-(2,2-diphenylcyclopropyl)oxirane
• CAS: 188774-77-8
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: LJONMYSJFBDGNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,1-Diphenyl-2-vinylcyclopropane 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 2-(2,2-二苯基环丙基)环氧乙烷
  参考文献：
  名称：

  Epoxidation and Oxygen Insertion Into Alkane Ch Bonds by Dioxirane Do Not Involve Detectable Radical Pathways

  摘要：

  AbstractThe dimethyldioxirane oxidation of α‐methylstyrene, trans‐cyclo‐octene, and 1‐vinyl‐2,2‐diphenylcyclopropane gave, under all reaction conditions employed, the corresponding epoxides in high yields. No radical products from allylic oxidation, from trans/cis isomerization, or from cyclopropylcarbinyl rearrangement (radical clock) were observed. Even for these alkenes, which are prone to radical reactions, the previously established electrophilic concerted mechanism applies, rather than the recently proposed radical mechanism. The selective hydroxylation of (–)‐2–phenylbutane by dimethyldioxirane gave only (– )‐2–phenylbutan‐2‐ol with complete retention of configuration and no loss of optical purity. Thus, a radical‐chain oxidation is also discounted in the oxygen insertion into hydrocarbon C‐H bonds for dioxiranes.

  DOI：

  10.1002/chem.19970030117

文献信息

• Epoxidation and Oxygen Insertion Into Alkane Ch Bonds by Dioxirane Do Not Involve Detectable Radical Pathways
  作者：Waldemar Adam、Ruggero Curci、Lucia D'Accolti、Anna Dinoi、Caterina Fusco、Francesco Gasparrini、Ralph Kluge、Rodrigo Paredes、Manfred Schulz、Alexander K. Smerz、L. Angela Veloza、Stephan Weinkötz、Roland Winde

  DOI：10.1002/chem.19970030117

  日期：1997.1

  AbstractThe dimethyldioxirane oxidation of α‐methylstyrene, trans‐cyclo‐octene, and 1‐vinyl‐2,2‐diphenylcyclopropane gave, under all reaction conditions employed, the corresponding epoxides in high yields. No radical products from allylic oxidation, from trans/cis isomerization, or from cyclopropylcarbinyl rearrangement (radical clock) were observed. Even for these alkenes, which are prone to radical reactions, the previously established electrophilic concerted mechanism applies, rather than the recently proposed radical mechanism. The selective hydroxylation of (–)‐2–phenylbutane by dimethyldioxirane gave only (– )‐2–phenylbutan‐2‐ol with complete retention of configuration and no loss of optical purity. Thus, a radical‐chain oxidation is also discounted in the oxygen insertion into hydrocarbon C‐H bonds for dioxiranes.