methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate | 149095-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate
• 英文别名: methyl (2R,4R)-2-tert-butyl-4-formyl-1,3-oxazolidine-3-carboxylate
• CAS: 149095-56-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: SYOZBVZWKQXQEC-JGVFFNPUSA-N

物化性质

• 沸点：
  299.0±40.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  一氧化碳 、 methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate 在 di-μ-chlorobis(norbornadiene)dirhodium(I) 、 氢气 、 三苯基膦 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、8.0 MPa 条件下， 反应 12.0h， 生成 methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate 、 methyl (2R,5R)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate 、 methyl (2R,4S)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Highly stereoselective hydroformylation of a (2R)-2-tert-butyl-Δ4-1,3-oxazoline derivative

  摘要：

  Methyl (2R)-2-tert-butyl-DELTA4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.

  DOI：

  10.1016/0022-328x(93)80213-u
• 作为产物：
  描述：

  2-t-butyl-3-methoxycarbonyl-2,3-dihydrooxazole 在 dichloro[bis(diphenylphosphino)butane]palladium 氢气 、 tin(ll) chloride 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、8.0 MPa 条件下， 反应 15.0h， 以22%的产率得到
  参考文献：
  名称：

  Highly stereoselective hydroformylation of a (2R)-2-tert-butyl-Δ4-1,3-oxazoline derivative

  摘要：

  Methyl (2R)-2-tert-butyl-DELTA4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.

  DOI：

  10.1016/0022-328x(93)80213-u

文献信息

• Highly stereoselective hydroformylation of a (2R)-2-tert-butyl-Δ4-1,3-oxazoline derivative
  作者：László Kollár、Pétér Sándor

  DOI：10.1016/0022-328x(93)80213-u

  日期：1993.2

  Methyl (2R)-2-tert-butyl-DELTA4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyl-oxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.