(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one | 193214-03-8

• 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: (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one
• 英文别名: (1S,5S,8S,9R)-9-(4-nitrophenyl)-5-phenyl-3,10,11-trioxa-6-azatricyclo[6.2.1.01,6]undecan-7-one
• CAS: 193214-03-8
• 化学式: C₁₉H₁₆N₂O₆
• 分子量: 368.346
• InChiKey: ASYLRALSQHUGNY-VXNCWWDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one 在 lithium hydroxide 、 三甲基氯硅烷 、 水 、 双氧水 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 ethyl (2S,3R)-2,3-dihydroxy-3-(4-nitrophenyl)propanoate
  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：

  对硝基苯甲醛 、 (S)-4-(2-Diazo-acetyl)-5-phenyl-morpholin-3-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以21%的产率得到(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-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

文献信息

• Highly selective chirally templated isomünchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-dihydroxyacid
  作者：Michael G.B Drew、Marion Fengler-Veith、Laurence M Harwood、Archie W Jahans

  DOI：10.1016/s0040-4039(97)00919-2

  日期：1997.6

  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.