(S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one | 193214-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one
• CAS: 193214-06-1
• 化学式: C₁₉H₁₈N₂O₇
• 分子量: 386.361
• InChiKey: IFPXWVWCYFXKKA-NXHRZFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130.21
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以74%的产率得到(2S,3R)-3-(4-cyanophenyl)-2,3-dihydroxypropanoic acid
  参考文献：
  名称：

  Highly selective chirally templated isomünchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-dihydroxyacid

  摘要：

  Additions of p-nitro- and p-methoxybenzaldehyde to isomunchnone derivatives of (5S)-phenyloxazin-3-one and -2,3-dione led to corresponding adducts (3,4,6) with excellent diastereofacial and exo-selectivity, Hydrolysis and subsequent cleavage of adduct 3 permitted recovery of the original template and furnished dihydroxyacid 9 that was transformed into the known ethyl ester 10. Comparison of its optical rotation with the literature value confirmed its high optical purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00919-2
• 作为产物：
  描述：

  (S)-4-(2-Diazo-acetyl)-5-phenyl-morpholin-3-one 在 dirhodium tetraacetate 水 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one
  参考文献：
  名称：

  Highly selective chirally templated isomünchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-dihydroxyacid

  摘要：

  Additions of p-nitro- and p-methoxybenzaldehyde to isomunchnone derivatives of (5S)-phenyloxazin-3-one and -2,3-dione led to corresponding adducts (3,4,6) with excellent diastereofacial and exo-selectivity, Hydrolysis and subsequent cleavage of adduct 3 permitted recovery of the original template and furnished dihydroxyacid 9 that was transformed into the known ethyl ester 10. Comparison of its optical rotation with the literature value confirmed its high optical purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00919-2