2-isopropyl-2-phenyloxirane | 1177357-67-3

• 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: (2R)-2-phenyl-2-propan-2-yloxirane
• CAS: 1177357-67-3
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: VJOWUFINYRBNJV-LLVKDONJSA-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 (2S,3S)-2-(1,3-dioxobenzo[de]isoquinolin-2-yl)-3-methylpentanoic acid 、 C₂₆H₃₆F₆FeN₆O₆S₂ 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到2-isopropyl-2-phenyloxirane
  参考文献：
  名称：

  非血红素铁催化剂和氨基酸配体在H2O2活化中对α-烷基取代苯乙烯的不对称环氧化的协同作用

  摘要：

  通过使用手性铁络合物作为催化剂，使用N-保护的氨基酸（AAs）作为大分子配体，描述了使用水为H 2 O 2的α-取代的苯乙烯的高度对映选择性环氧化。氨基酸与铁中心协同作用，以促进H 2 O 2的有效活化，从而在较短的反应时间内以良好的收率和立体选择性（高达97％ee）催化这种具有挑战性的底物的环氧化 。

  DOI：

  10.1002/anie.201410557

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.
• Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States
  作者：O. Andrea Wong、Bin Wang、Mei-Xin Zhao、Yian Shi

  DOI：10.1021/jo900739q

  日期：2009.8.21

  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.
• Synergistic Interplay of a Non-Heme Iron Catalyst and Amino Acid Coligands in H₂O₂Activation for Asymmetric Epoxidation of α-Alkyl-Substituted Styrenes
  作者：Olaf Cussó、Xavi Ribas、Julio Lloret-Fillol、Miquel Costas

  DOI：10.1002/anie.201410557

  日期：2015.2.23

  Highly enantioselective epoxidation of α‐substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N‐protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities

  通过使用手性铁络合物作为催化剂，使用N-保护的氨基酸（AAs）作为大分子配体，描述了使用水为H 2 O 2的α-取代的苯乙烯的高度对映选择性环氧化。氨基酸与铁中心协同作用，以促进H 2 O 2的有效活化，从而在较短的反应时间内以良好的收率和立体选择性（高达97％ee）催化这种具有挑战性的底物的环氧化 。