Z 3-oxazolidinecarboxylic acid, 2-(3-methoxy-1-methyl-3-oxo-1-propenyl)-4-methyl-5-phenyl methyl ester | 138921-41-2

• 分子结构分类: 有机化合物
• 英文名称: Z 3-oxazolidinecarboxylic acid, 2-(3-methoxy-1-methyl-3-oxo-1-propenyl)-4-methyl-5-phenyl methyl ester
• CAS: 138921-41-2
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: ZAPZVXGIEUSDKK-DNESWEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z 3-oxazolidinecarboxylic acid, 2-(3-methoxy-1-methyl-3-oxo-1-propenyl)-4-methyl-5-phenyl methyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 、 水 为溶剂， 以33%的产率得到(2S,4S,5R)-2-((R)-2-Methoxycarbonyl-1-methyl-ethyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric hydrogenation of 3-methyl-fumaric and maleic ester monoaldehydes protected as neph-derived oxazolidines

  摘要：

  The hydrogenation of 3-methyl-fumaric and maleic ester mono aldehydes protected as oxazolidines of nor-ephedrine (NEPH) derivation has been studied. This transformation takes place with moderate to good pi-face stereodifferentiation and allows the preparation of non-racemic 3-methyl-succinaldehydic acid methyl ester (1, R = Me). The factors dictating the diastereocontrol are discussed.

  DOI：

  10.1016/s0040-4020(01)89738-6
• 作为产物：
  描述：

  t-butyl 4,4-dimethoxy-3-methyl-2-butenoate 在 氢氧化钾 、 三氟化硼乙醚 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.17h， 生成 Z 3-oxazolidinecarboxylic acid, 2-(3-methoxy-1-methyl-3-oxo-1-propenyl)-4-methyl-5-phenyl methyl ester
  参考文献：
  名称：

  Asymmetric hydrogenation of 3-methyl-fumaric and maleic ester monoaldehydes protected as neph-derived oxazolidines

  摘要：

  The hydrogenation of 3-methyl-fumaric and maleic ester mono aldehydes protected as oxazolidines of nor-ephedrine (NEPH) derivation has been studied. This transformation takes place with moderate to good pi-face stereodifferentiation and allows the preparation of non-racemic 3-methyl-succinaldehydic acid methyl ester (1, R = Me). The factors dictating the diastereocontrol are discussed.

  DOI：

  10.1016/s0040-4020(01)89738-6