(2S)-3,3-diphenyloxiran-2-carbaldehyde

• 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: (2S)-3,3-diphenyloxiran-2-carbaldehyde
• 英文别名: (S)-3,3-diphenyloxirane-2-carbaldehyde；(2S)-3,3-diphenyloxirane-2-carbaldehyde
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: LRCOJUJUDZXWJO-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2R,4'S,5'R)-(-)-2-chloro-1,1-diphenyl-2-(4-methyl-5-phenyl-2-oxazolin-2-yl)ethan-1-ol 在 sodium hydroxide 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 12.5h， 生成 (2S)-3,3-diphenyloxiran-2-carbaldehyde
  参考文献：
  名称：

  On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds

  摘要：

  Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00611-1

文献信息

• Fluorinated Organocatalysts for the Enantioselective Epoxidation of Enals: Molecular Preorganisation by the Fluorine-Iminium Ion Gauche Effect
  作者：Eva-Maria Tanzer、Lucie E. Zimmer、W. Bernd Schweizer、Ryan Gilmour

  DOI：10.1002/chem.201201316

  日期：2012.9.3

  The fluorine‐iminium ion gauche effect is triggered upon union of a secondary β‐fluoroamine and an α,β‐unsaturated aldehyde, providing a useful strategy for controlling the molecular topology of intermediates that are central to organocatalytic processes. The β‐fluoroamine (S)‐2‐(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β‐unsaturated aldehydes

  当仲β-氟胺和α，β-不饱和醛结合后会触发氟亚胺离子的网状效应，为控制有机催化过程中重要的中间体的分子拓扑提供了有用的策略。β-氟胺（S）-2-（氟二苯基甲基）吡咯烷（1）是α，β-不饱和醛对映选择性环氧化的有效催化剂。结构编辑的过程表明，该催化剂的效率归因于嵌入在β-氟亚胺基序中的（氟二苯基）甲基。1催化具有挑战性的环状α，β-二取代，β，β-二取代和α，β，β-三取代的烯醛继续进行优异的对映体控制（高达98％  ee）。
• Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes
  作者：Saverio Florio、Vito Capriati、Renzo Luisi、Alessandro Abbotto

  DOI：10.1016/s0040-4039(99)01480-x

  日期：1999.10

  Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Science Ltd. All rights reserved.
• On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds
  作者：Saverio Florio、Vito Capriati、Renzo Luisi、Alessandro Abbotto、Daniel J Pippel

  DOI：10.1016/s0040-4020(01)00611-1

  日期：2001.7

  Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.