(2R,4'S,5'R)-(-)-2-(3,3-diphenyloxiranyl)-4-methyl-5-phenyl-2-oxazoline | 252880-57-2

• 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: (2R,4'S,5'R)-(-)-2-(3,3-diphenyloxiranyl)-4-methyl-5-phenyl-2-oxazoline
• 英文别名: (4S,5R)-2-[(2R)-3,3-diphenyloxiran-2-yl]-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 252880-57-2
• 化学式: C₂₄H₂₁NO₂
• 分子量: 355.436
• InChiKey: LCNVTDXVWPCEOF-HSQYWUDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4'S,5'R)-(-)-2-(3,3-diphenyloxiranyl)-4-methyl-5-phenyl-2-oxazoline 在 三氟甲烷磺酸甲酯 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到(2R)-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
• 作为产物：
  描述：

  去甲麻黄碱 在 sodium hydroxide 、 次氯酸叔丁酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 异丙醇 为溶剂， 反应 3.75h， 生成 (2R,4'S,5'R)-(-)-2-(3,3-diphenyloxiranyl)-4-methyl-5-phenyl-2-oxazoline
  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

• 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.