2-isopropyl-2-phenyloxirane | 403501-36-0

• 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: 2-isopropyl-2-phenyloxirane
• 英文别名: (2S)-2-phenyl-2-propan-2-yloxirane
• CAS: 403501-36-0
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: VJOWUFINYRBNJV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  3-methyl-2-phenyl-1-butene 在 Oxone 、 乙二胺四乙酸 、 (3aR,6S,7aR)-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3',7-dione 、 四丁基硫酸氢铵 、 edetate disodium 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 2-isopropyl-2-phenyloxirane 、 2-isopropyl-2-phenyloxirane
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States

  摘要：

  Asymmetric epoxidation of olefins by using an alpha,alpha-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The alpha,alpha-dimethyl group has significant impact oil spiro and planar transition states.

  DOI：

  10.1021/jo900739q

文献信息

• Isomerization of Terminal Epoxides by a [Pd–H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study
  作者：Devendra J. Vyas、Evgeny Larionov、Céline Besnard、Laure Guénée、Clément Mazet

  DOI：10.1021/ja400325w

  日期：2013.4.24

  An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.