乙基(2S)-3,4-二氢-2H-吡咯-2-羧酸酯 | 172879-74-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙基(2S)-3,4-二氢-2H-吡咯-2-羧酸酯
• 英文名称: ethyl (S)-3,4-dihydro-2H-pyrrole-2-carboxylate
• 英文别名: (S)-ethyl 3,4-dihydro-2H-pyrrole-2-carboxylate；ethyl (2S)-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS: 172879-74-2
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: GIBYAWAMDZXFJS-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基(2S)-3,4-二氢-2H-吡咯-2-羧酸酯 在 间氯过氧苯甲酸 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 生成 吡咯-2-羧酸乙酯
  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：

  L-焦谷氨酸乙酯 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以47%的产率得到乙基(2S)-3,4-二氢-2H-吡咯-2-羧酸酯
  参考文献：
  名称：

  An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones

  摘要：

  Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Delta(1)-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00097-7

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.
• An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones
  作者：Qian Xia、Bruce Ganem

  DOI：10.1016/s0040-4039(02)00097-7

  日期：2002.2

  Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Delta(1)-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported. (C) 2002 Elsevier Science Ltd. All rights reserved.