(4S,5R)-(-)-2,4-dimethyl-5-phenyl-2-oxazoline | 205178-46-7

• 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: (4S,5R)-(-)-2,4-dimethyl-5-phenyl-2-oxazoline
• 英文别名: (4S,5R)-2,4-dimethyl-5-phenyl-2-oxazoline；cis-2,4-Dimethyl-5-phenyl-Δ²-oxazolin；(4S,5R)-2,4-dimethyl-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 205178-46-7
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: MMMAYBWIULJYOK-KWQFWETISA-N

物化性质

• 沸点：
  258.6±29.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-(-)-2,4-dimethyl-5-phenyl-2-oxazoline 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
• 作为产物：
  描述：

  原乙酸三甲酯 、 去甲麻黄碱 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以91%的产率得到(4S,5R)-(-)-2,4-dimethyl-5-phenyl-2-oxazoline
  参考文献：
  名称：

  An Efficient and Versatile Method for the Synthesis of Optically Active 2-Oxazolines: An Acid-catalyzed Condensation of Ortho Esters with Amino Alcohols

  摘要：

  DOI：

  10.1021/jo971161x

文献信息

• An Efficient and Versatile Method for the Synthesis of Optically Active 2-Oxazolines: An Acid-catalyzed Condensation of Ortho Esters with Amino Alcohols
  作者：Kazuyuki Kamata、Isao Agata、A. I. Meyers

  DOI：10.1021/jo971161x

  日期：1998.5.1
• 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.