3-(((allyloxy)carbonyl)methyl)-4,5-diphenyl-1-oxazolin-2-one | 135875-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(((allyloxy)carbonyl)methyl)-4,5-diphenyl-1-oxazolin-2-one
• 英文别名: Prop-2-enyl 2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetate
• CAS: 135875-40-0
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: UIUXJGNWKFOOAE-UHFFFAOYSA-N

物化性质

• 沸点：
  483.6±55.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(((allyloxy)carbonyl)methyl)-4,5-diphenyl-1-oxazolin-2-one 在 四(三苯基膦)钯 O-苄基羟胺 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (+/-)-anti-N-((tert-butoxycarbonyl)(diethylphosphono)methyl)-2-(2-oxo-4,5-diphenyl-1-oxazolinyl)-3-hydroxy-7-heptenamide
  参考文献：
  名称：

  Diastereoselective synthesis of the carbacephem framework

  摘要：

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.

  DOI：

  10.1021/jo00055a013
• 作为产物：
  描述：

  3-溴丙烯 、 3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以94%的产率得到3-(((allyloxy)carbonyl)methyl)-4,5-diphenyl-1-oxazolin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of the carbacephem framework

  摘要：

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.

  DOI：

  10.1021/jo00055a013

文献信息

• Facile syntheses and rearrangements of peptide derived β-lactams
  作者：Francine Farouz、Marvin J. Miller

  DOI：10.1016/s0040-4039(00)92692-3

  日期：1991.7

  Stereoselective aldol condensation of a 4,5-diphenyl-oxazolin-2-one (Ox) glycine provided alpha-amino-beta-hydroxy acid 4, which, after coupling with phenylglycine derivatives, was directly cyclized to beta-lactams. Ozonolysis cleaved both the Ox and isopropylidene groups and initiated a Chapman rearrangement to the corresponding alpha-benzamido-beta-acyl-2-azetidinone 8. Subsequent reduction induced a diastereoselective rearrangement to the corresponding gamma-lactone 13.
• Diastereoselective synthesis of the carbacephem framework
  作者：Bruce T. Lotz、Marvin J. Miller

  DOI：10.1021/jo00055a013

  日期：1993.1

  A short, versatile, and diastereoselective method of preparing carbacephems has been developed. The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde. In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final bicyclic beta-lactam are set. This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.