(S)-3,4-dihydro-5-methylthio-2-pivaloyloxymethyl-2H-pyrrole | 172879-77-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚氨硫酯类
• 英文名称: (S)-3,4-dihydro-5-methylthio-2-pivaloyloxymethyl-2H-pyrrole
• 英文别名: [(2S)-5-methylsulfanyl-3,4-dihydro-2H-pyrrol-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 172879-77-5
• 化学式: C₁₁H₁₉NO₂S
• 分子量: 229.343
• InChiKey: RIISZQXNWNPBLQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3,4-dihydro-5-methylthio-2-pivaloyloxymethyl-2H-pyrrole 在 W-2 Raney-Ni 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 (3S,5aS)-3-pivaloyloxymethyltetrahydropyrrolo[1,2-b]oxaziridine
  参考文献：
  名称：

  Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

  摘要：

  A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable alpha-methoxy-N-carboxylate ion. Which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00110-6
• 作为产物：
  描述：

  乙基5-硫代-L-脯氨酸酯 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 42.0h， 生成 (S)-3,4-dihydro-5-methylthio-2-pivaloyloxymethyl-2H-pyrrole
  参考文献：
  名称：

  Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

  摘要：

  A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable alpha-methoxy-N-carboxylate ion. Which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00110-6

文献信息

• Synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide
  作者：Pedro de March、Marta Figueredo、Josep Font、Timothy Gallagher、Sergio Milán

  DOI：10.1039/c39950002097

  日期：——

  The synthesis of a series of new enantiopure 3,4-dihydro-2H-pyrrole derivatives including the title nitrone and its cycloaddition product to dimethyl acetylenedicarboxylate is described.
• Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Timothy Gallagher、Sergio Milán

  DOI：10.1016/s0957-4166(02)00110-6

  日期：2002.3

  A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable alpha-methoxy-N-carboxylate ion. Which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.