甲基(2S)-2-(2-甲基-1H-吡咯-1-基)丙酸酯 | 189231-36-5

• 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: 甲基(2S)-2-(2-甲基-1H-吡咯-1-基)丙酸酯
• 中文别名: 2H-吡喃-2-酮,四氢-4-羟基-6-(1-甲基乙基)-,顺-(9CI)
• 英文名称: (-)-Methyl (2S)-2-(2-methyl-1H-pyrrol-1-yl)propanoate
• 英文别名: methyl (2S)-(2-methyl-1H-pyrrol-1-yl)propanoate；(S)-Methyl 2-(2-methyl-1H-pyrrol-1-yl)propanoate；methyl (2S)-2-(2-methylpyrrol-1-yl)propanoate
• CAS: 189231-36-5
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: BRBQAHGYKACIQL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基(2S)-2-(2-甲基-1H-吡咯-1-基)丙酸酯 在 氧气 、 焦磷酸硫胺素 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到(S)-methyl 2-(2-methylene-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate
  参考文献：
  名称：

  The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives

  摘要：

  Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amines, amino alcohols and amino acid esters. The photooxygenation of these pyrrole derivatives in the presence of a photosensitiser furnishes the corresponding alpha,beta,gamma,delta-unsaturated gamma-lactams as the major products in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00140-4
• 作为产物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 5-chloro-3-penten-2-one 在 三乙胺 作用下， 以 水 、 苯 为溶剂， 反应 3.0h， 以80%的产率得到甲基(2S)-2-(2-甲基-1H-吡咯-1-基)丙酸酯
  参考文献：
  名称：

  Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives

  摘要：

  5-Chloro-3-penten-2-one reacts with the amino group of homochiral amines, amino alcohols, amino acid esters to form corresponding 2-pyrrole derivatives in good yield and without racemization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00035-9

文献信息

• Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives
  作者：Ayhan S. Demir、Idris M. Akhmedov、Özge Şeşenoglu、Onur Alptürk、Sinem Apaydın、Zuhal Gerçek、Nezire Ibrahimzade

  DOI：10.1039/b008317h

  日期：——

  The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters.

  介绍了将手性胺、氨基醇、氨基酸及其酯的氨基基团转化为具有各种卤代烯酮的手性2-取代吡咯衍生物的方法。该转化在良好产率下进行，且不会发生消旋化。氨基醇能够合成2-苯基吡咯衍生物，而氨基酸或其酯则不能。
• Clean and efficient microwave-solvent-free conversion of homochiral amines, α-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives
  作者：Feray Aydogan、Ayhan S. Demir

  DOI：10.1016/j.tet.2005.01.120

  日期：2005.3

  Efficient synthesis of 1,2-disubstituted homochiral pyrroles has been achieved by a two-component coupling of chloroenones and amine compounds on the surface of silica gel without any solvent under microwave irradiation.

  通过在微波辐射下在没有任何溶剂的情况下硅胶表面上的氯烯酮和胺化合物的两组分偶联，已经实现了1,2-二取代的高手性吡咯的有效合成。
• Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives
  作者：Ayhan S. Demir、Idris M. Akhmedov、Cihangir Tanyeli、Zuhal Gerçek、Raik A. Gadzhili

  DOI：10.1016/s0957-4166(97)00035-9

  日期：1997.3

  5-Chloro-3-penten-2-one reacts with the amino group of homochiral amines, amino alcohols, amino acid esters to form corresponding 2-pyrrole derivatives in good yield and without racemization. (C) 1997 Elsevier Science Ltd.
• The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives
  作者：Ayhan S. Demir、Feray Aydogan、Idris M. Akhmedov

  DOI：10.1016/s0957-4166(02)00140-4

  日期：2002.4

  Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amines, amino alcohols and amino acid esters. The photooxygenation of these pyrrole derivatives in the presence of a photosensitiser furnishes the corresponding alpha,beta,gamma,delta-unsaturated gamma-lactams as the major products in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.