(S)-4-(2-Diazo-acetyl)-5-phenyl-morpholine-2,3-dione | 190582-13-9

• 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-(2-Diazo-acetyl)-5-phenyl-morpholine-2,3-dione
• 英文别名: 2-Diazonio-1-[(5S)-2,3-dioxo-5-phenylmorpholin-4-yl]ethen-1-olate；(5S)-4-(2-diazoacetyl)-5-phenylmorpholine-2,3-dione
• CAS: 190582-13-9
• 化学式: C₁₂H₉N₃O₄
• 分子量: 259.221
• InChiKey: OGRPUCMSHFLYFB-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对硝基苯甲醛 、 (S)-4-(2-Diazo-acetyl)-5-phenyl-morpholine-2,3-dione 在 tetrakis(trifluoroacetato)rhodium(II) 作用下， 以 二氯甲烷 为溶剂， 以45%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]undecane-2,7-dione
  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：

  succinimidyl diazoacetate 、 (S)-5-Phenyl-morpholine-2,3-dione 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以32%的产率得到(S)-4-(2-Diazo-acetyl)-5-phenyl-morpholine-2,3-dione
  参考文献：
  名称：

  Novel Chiral Templates for 1,3-Oxazolium-4-olate (Isomünchnone) Cycloadditions: (5 R)- and (5 S)-Phenyloxazin-2,3-dione

  摘要：

  Cycloadducts (4-10) were synthesised From isomunchnone derivatives of (5R)- and (SS)-phenyloxazin-2,3-dione by rhodium(II)-catalysed decomposition. High endo/exo-selectivities for additions to carbon-carbon dipolarophiles were observed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00557-1

文献信息

• Novel Chiral Templates for 1,3-Oxazolium-4-olate (Isomünchnone) Cycloadditions: (5 R)- and (5 S)-Phenyloxazin-2,3-dione
  作者：Richard Angell、Michael G.B. Drew、Marion Fengler-Veith、Harry Finch、Laurence M. Harwood*、Archie W. Jahans、Toby T. Tucker

  DOI：10.1016/s0040-4039(97)00557-1

  日期：1997.4

  Cycloadducts (4-10) were synthesised From isomunchnone derivatives of (5R)- and (SS)-phenyloxazin-2,3-dione by rhodium(II)-catalysed decomposition. High endo/exo-selectivities for additions to carbon-carbon dipolarophiles were observed. (C) 1997 Elsevier Science Ltd.
• 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.