(S_C)-N-phthaloylmethionine sulfoxide | 147059-17-4

• 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: (S_C)-N-phthaloylmethionine sulfoxide
• 英文别名: N-phthaloyl methionine sulfoxide；(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylsulfinylbutanoic acid
• CAS: 147059-17-4
• 化学式: C₁₃H₁₃NO₅S
• 分子量: 295.316
• InChiKey: QYXFLPXRIFFGJI-SMNKDYLDSA-N

物化性质

• 沸点：
  594.3±45.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S_C)-N-phthaloylmethionine sulfoxide 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 methyl 7-oxo-4,5-dihydro-3H,7H-[1,4]thiazepino[3,4-a]isoindole-5-carboxylate
  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， 以 丙酮 为溶剂， 生成 (S_C)-N-phthaloylmethionine sulfoxide
  参考文献：
  名称：

  Griesbeck, Axel G., Chimia, 1998, vol. 52, # 6, p. 272 - 283

  摘要：

  DOI：

文献信息

• Biocatalytic and chemical routes to all the stereoisomers of methionine and ethionine sulfoxides
  作者：Herbert L Holland、Peter R Andreana、Frances M Brown

  DOI：10.1016/s0957-4166(99)00271-2

  日期：1999.7

  Biotransformations of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine by Beauveria bassiana ATCC 7159 or Beauveria caledonica ATCC 64970 produce the corresponding (S-S) sulfoxides in good yield and diastereomeric excess. Pure (SSSC) diastereomers can be obtained from L-series substrates by crystallisation of the biotransformation extract, and the corresponding (SSRC) products obtained from D-series substrates by chromatography of the biotransformation extract. Hydrogen peroxide-catalysed oxidation of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine gives diastereomeric mixtures from which the (SSSC) and (RSRC) diastereomers can be obtained by crystallisation, and the (SSRC) and (RSSC) diastereomers obtained by chromatography. N-Cbz- and N-t-Boc methionines are also converted to sulfoxides with predominant (S-S) configuration by both B, bassiana and B. caledonica, but the isolated yields and d.e. of products were generally lower than those obtained from the N-phthaloyl substrates.Removal of the N-phthaloyl group from diastereomerically pure methionine and ethionine sulfoxides gave the corresponding amino acid sulfoxides in high yield; removal of N-Cbz and N-t-Boc groups from protected methionine sulfoxides was also achieved without loss of configuration at sulfur. (C) 1994 Elsevier Science Ltd. All rights reserved.
• Griesbeck, Axel G.; Hirt, Joachim, Liebigs Annalen, 1995, # 11, p. 1957 - 1962
  作者：Griesbeck, Axel G.、Hirt, Joachim

  DOI：——

  日期：——
• Griesbeck, Axel G., Chimia, 1998, vol. 52, # 6, p. 272 - 283
  作者：Griesbeck, Axel G.

  DOI：——

  日期：——
• 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.