N-phthaloyl methionine sulfone | 146983-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-phthaloyl methionine sulfone
• 英文别名: (2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylsulfonylbutanoic acid
• CAS: 146983-83-7
• 化学式: C₁₃H₁₃NO₆S
• 分子量: 311.315
• InChiKey: LHFMZTWTJXSQGK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-phthaloyl methionine sulfone 以 丙酮 为溶剂， 生成 2-<(3-Methylsulfonyl)propyl>-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Photochemistry of N-phthaloyl derivatives of methionine

  摘要：

  Photodecarboxylation of N-phthaloyl derivatives of methionine sulfoxide 1b and methionine sulfone 1c was observed in acetone as the major reaction. For 1a a fast electron transfer initiated cyclization which leads to the bicyclization product 3 (X-ray structure) was observed in the sensitized photolysis. Direct photolysis of 1a leads preferentially to the tricyclic product 4 and the decarboxylation product 5. The methionine methyl esters 6a-c showed electon transfer initiated cyclization (for 6a) and disproportionation (for 6b), whereas 6c proved to be photostable.

  DOI：

  10.1016/0040-4039(93)85100-b
• 作为产物：
  描述：

  (alphaS)-1,3-二氢-alpha-[2-(甲硫基)乙基]-1,3-二氧代-2H-异吲哚-2-乙酸 在 双氧水 作用下， 反应 24.0h， 以31%的产率得到N-phthaloyl methionine sulfone
  参考文献：
  名称：

  Photochemistry of N-phthaloyl derivatives of methionine

  摘要：

  Photodecarboxylation of N-phthaloyl derivatives of methionine sulfoxide 1b and methionine sulfone 1c was observed in acetone as the major reaction. For 1a a fast electron transfer initiated cyclization which leads to the bicyclization product 3 (X-ray structure) was observed in the sensitized photolysis. Direct photolysis of 1a leads preferentially to the tricyclic product 4 and the decarboxylation product 5. The methionine methyl esters 6a-c showed electon transfer initiated cyclization (for 6a) and disproportionation (for 6b), whereas 6c proved to be photostable.

  DOI：

  10.1016/0040-4039(93)85100-b

文献信息

• Photochemistry of N-phthaloyl derivatives of methionine
  作者：Axel G. Griesbeck、Harald Mauder、Ingrid Müller、Eva-Maria Peters、Karl Peters、Hans Georg von Schnering

  DOI：10.1016/0040-4039(93)85100-b

  日期：1993.1

  Photodecarboxylation of N-phthaloyl derivatives of methionine sulfoxide 1b and methionine sulfone 1c was observed in acetone as the major reaction. For 1a a fast electron transfer initiated cyclization which leads to the bicyclization product 3 (X-ray structure) was observed in the sensitized photolysis. Direct photolysis of 1a leads preferentially to the tricyclic product 4 and the decarboxylation product 5. The methionine methyl esters 6a-c showed electon transfer initiated cyclization (for 6a) and disproportionation (for 6b), whereas 6c proved to be photostable.