trans-4,5-diphenyl-2-methyl-Δ²-oxazoline | 70369-11-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4,5-diphenyl-2-methyl-Δ²-oxazoline
• 英文别名: 2-methyl-4,5-diphenyl-4,5-dihydrooxazole；trans-4,5-diphenyl-2-methyl-2-oxazoline；2-methyl-4,5-diphenyloxazoline；(+/-)-2-methyl-4r,5t-diphenyl-4,5-dihydro-oxazole；(+/-)-2-Methyl-4r,5t-diphenyl-4,5-dihydro-oxazol；(4R,5R)-2-methyl-4,5-diphenyl-4,5-dihydro-1,3-oxazole
• CAS: 70369-11-8；78974-56-8；133649-09-9
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: JTPIBZBMQLKGEE-HZPDHXFCSA-N

物化性质

• 沸点：
  350.4±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  trans-4,5-diphenyl-2-methyl-Δ²-oxazoline 以 氯仿 为溶剂， 生成 threo-2-Acetamino-1.2-diphenyl-aethan-1-ol
  参考文献：
  名称：

  Bromination of alkenes in acetonitrile. A rate and product study

  摘要：

  The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols. These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts. These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes. The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3- with the alkene. The incorporation of MeCN was Markovnikov and stereospecifically anti. The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations. A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

  DOI：

  10.1021/jo00009a027
• 作为产物：
  描述：

  threo-2-Acetamino-1.2-diphenyl-aethan-1-ol 生成 trans-4,5-diphenyl-2-methyl-Δ²-oxazoline
  参考文献：
  名称：

  KOPCZYNSKI T.; VOELKEL A., ZESZ. NAUK. PPOZN., 1980, NO 15, 81-88

  摘要：

  DOI：

文献信息

• Svoboda et al., Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 1426,1437
  作者：Svoboda et al.

  DOI：——

  日期：——
• Stereoselective One-Pot Synthesis of Oxazolines
  作者：Saumen Hajra、Sukanta Bar、Debarshi Sinha、Biswajit Maji

  DOI：10.1021/jo8003937

  日期：2008.6.1

  Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)(2) or Zn(OTf)(2) is reported to furnish oxazolines in one pot and good yields. The reaction is equally applicable to chalcones.
• Kopczynski; Voelkel, Polish Journal of Chemistry, 2001, vol. 75, # 9, p. 1317 - 1325
  作者：Kopczynski、Voelkel

  DOI：——

  日期：——
• KOPCZYNSKI, T.;VELKEL, A., POL. J. CHEM., 1983, 57, N 1-3, 107-111
  作者：KOPCZYNSKI, T.、VELKEL, A.

  DOI：——

  日期：——