3-(4-Acetylphenyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one | 1262802-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-Acetylphenyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one
• 英文别名: 3-(4-acetylphenyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one
• CAS: 1262802-49-2
• 化学式: C₁₅H₂₀NO₆P
• 分子量: 341.301
• InChiKey: YGWWZADLUIZWSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  epoxy-1,2 ethyl phosphonate de diethyle 、 4-乙酰苯基异氰酸酯 在 ytterbium(III) chloride hexahydrate 、 2,6-二[(4R)-4-苯基-2-恶唑啉基]吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-(4-Acetylphenyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one 、 diethyl N-(4-acetylphenyl)-2-oxo-oxazolidin-5-ylphosphonate 、 diethyl N-(4-acetylphenyl)-2-oxo-oxazolidin-5-ylphosphonate
  参考文献：
  名称：

  The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates

  摘要：

  A [3+2] cycloaddition of diethyl 1 2-oxiranephosphonate to aryl isocyanates catalyzed by lanthanide cations is described The reaction is highly regioselective and 5-substituted 2-oxazolidinone phosphonates are obtained with a regioselectivity greater than 95 5 with respect to the 4-substituted regioisomer and in up to 84% yield When 20 mol % of Pybox-Yb3+ is used as a catalyst enantiomerically enriched products are obtained in up to 75% ee depending on the reaction conditions and the nature of the isocyanate Low temperatures benefit asymmetric induction but have an adverse effect on the regioselectivity for para-substituted aryl isocyanates (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.028

文献信息

• The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates
  作者：Maria Teresa Barros、Ana Maria Faísca Phillips

  DOI：10.1016/j.tetasy.2010.10.028

  日期：2010.11

  A [3+2] cycloaddition of diethyl 1 2-oxiranephosphonate to aryl isocyanates catalyzed by lanthanide cations is described The reaction is highly regioselective and 5-substituted 2-oxazolidinone phosphonates are obtained with a regioselectivity greater than 95 5 with respect to the 4-substituted regioisomer and in up to 84% yield When 20 mol % of Pybox-Yb3+ is used as a catalyst enantiomerically enriched products are obtained in up to 75% ee depending on the reaction conditions and the nature of the isocyanate Low temperatures benefit asymmetric induction but have an adverse effect on the regioselectivity for para-substituted aryl isocyanates (C) 2010 Elsevier Ltd All rights reserved