ethyl 2-(2'-formylpyrrol-1-yl)propanoate | 214478-40-7

• 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
• 英文名称: ethyl 2-(2'-formylpyrrol-1-yl)propanoate
• 英文别名: (S)-Ethyl 2-(2-formyl-1H-pyrrol-1-yl)propanoate；ethyl 2-(2-formylpyrrol-1-yl)propanoate
• CAS: 214478-40-7
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: CTNICYZNJBUCOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  296.7±20.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2'-formylpyrrol-1-yl)propanoate 在 sodium hydroxide 、 phosphate buffer 7.0 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 4-hydroxy-5-methyl-2-<(E)-N-(1'-carboxyethyl)pyrrolyl-2-methylidene>-2H-furan-3-one
  参考文献：
  名称：

  Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids

  摘要：

  Heating of pentoses with alanine in a ratio of 10:1 in aqueous solution at pH 7.0 generated the yellow 2-[(2-furyl)methylidene]-4-hydroxy-5-methyl-2H-furan-3-one (1), being well in line with data reported in the literature. Decreasing the relative concentrations of the pentose produced further colored nitrogen-containing compounds, among which (S)-4-hydroxy-5-methyl-2-[N-(1'-carboxyethyl)-pyrrolyl-2-methyldiene]-2H-furan-3-one (2) could be identified by spectroscopic and synthetic experiments. On the other hand, thermal treatment of an aqueous solution of pentose and L-alanine in the presence of furan-2-carboxaldehyde led to the formation of the novel red (2R)-4-oxo-3,5-bis-[(2-furyl)methylidene] tetrahydropyrrolo[1,2-c]-5(S)-(2-furyl)oxazolidine and its 5(R)-(2-furyl)oxazolidine diasteromer (3a/3b), which were characterized by several 1D- and 2D-NMR techniques, LC/MS, and UV-vis spectroscopy as well as by synthesis of the chromophoric substructure. In addition, the red compounds (S)-4-[(E)-1-formyl-2-(2-furyl)ethenyl]-5-(2-furyl)-2-[(E)-(2-furyl)methylidene]-2,3-dihydo-alpha-amino-3-oxo-1H-pyrrole-1-acetic acid (4b) and the corresponding 2-[(Z)-(2-furyl)-methylidene] isomer (4b) were identified in this Maillard mixture. Quantitative studies on the formation of these colorants clearly demonstrates the key role of 3-deoxypentos-2-ulose as an intermediate in the formation of 4a/4b. Reaction pathways leading to the colorants 2, 3a/3b, and 4a/4b from pentoses and alanine are discussed.

  DOI：

  10.1021/jf980477i
• 作为产物：
  描述：

  2-吡咯甲醛 、 2-碘丙酸乙酯 在 thallium (I) ethoxide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以72%的产率得到ethyl 2-(2'-formylpyrrol-1-yl)propanoate
  参考文献：
  名称：

  Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids

  摘要：

  Heating of pentoses with alanine in a ratio of 10:1 in aqueous solution at pH 7.0 generated the yellow 2-[(2-furyl)methylidene]-4-hydroxy-5-methyl-2H-furan-3-one (1), being well in line with data reported in the literature. Decreasing the relative concentrations of the pentose produced further colored nitrogen-containing compounds, among which (S)-4-hydroxy-5-methyl-2-[N-(1'-carboxyethyl)-pyrrolyl-2-methyldiene]-2H-furan-3-one (2) could be identified by spectroscopic and synthetic experiments. On the other hand, thermal treatment of an aqueous solution of pentose and L-alanine in the presence of furan-2-carboxaldehyde led to the formation of the novel red (2R)-4-oxo-3,5-bis-[(2-furyl)methylidene] tetrahydropyrrolo[1,2-c]-5(S)-(2-furyl)oxazolidine and its 5(R)-(2-furyl)oxazolidine diasteromer (3a/3b), which were characterized by several 1D- and 2D-NMR techniques, LC/MS, and UV-vis spectroscopy as well as by synthesis of the chromophoric substructure. In addition, the red compounds (S)-4-[(E)-1-formyl-2-(2-furyl)ethenyl]-5-(2-furyl)-2-[(E)-(2-furyl)methylidene]-2,3-dihydo-alpha-amino-3-oxo-1H-pyrrole-1-acetic acid (4b) and the corresponding 2-[(Z)-(2-furyl)-methylidene] isomer (4b) were identified in this Maillard mixture. Quantitative studies on the formation of these colorants clearly demonstrates the key role of 3-deoxypentos-2-ulose as an intermediate in the formation of 4a/4b. Reaction pathways leading to the colorants 2, 3a/3b, and 4a/4b from pentoses and alanine are discussed.

  DOI：

  10.1021/jf980477i

文献信息

• Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids
  作者：Thomas Hofmann

  DOI：10.1021/jf980477i

  日期：1998.10.1

  Heating of pentoses with alanine in a ratio of 10:1 in aqueous solution at pH 7.0 generated the yellow 2-[(2-furyl)methylidene]-4-hydroxy-5-methyl-2H-furan-3-one (1), being well in line with data reported in the literature. Decreasing the relative concentrations of the pentose produced further colored nitrogen-containing compounds, among which (S)-4-hydroxy-5-methyl-2-[N-(1'-carboxyethyl)-pyrrolyl-2-methyldiene]-2H-furan-3-one (2) could be identified by spectroscopic and synthetic experiments. On the other hand, thermal treatment of an aqueous solution of pentose and L-alanine in the presence of furan-2-carboxaldehyde led to the formation of the novel red (2R)-4-oxo-3,5-bis-[(2-furyl)methylidene] tetrahydropyrrolo[1,2-c]-5(S)-(2-furyl)oxazolidine and its 5(R)-(2-furyl)oxazolidine diasteromer (3a/3b), which were characterized by several 1D- and 2D-NMR techniques, LC/MS, and UV-vis spectroscopy as well as by synthesis of the chromophoric substructure. In addition, the red compounds (S)-4-[(E)-1-formyl-2-(2-furyl)ethenyl]-5-(2-furyl)-2-[(E)-(2-furyl)methylidene]-2,3-dihydo-alpha-amino-3-oxo-1H-pyrrole-1-acetic acid (4b) and the corresponding 2-[(Z)-(2-furyl)-methylidene] isomer (4b) were identified in this Maillard mixture. Quantitative studies on the formation of these colorants clearly demonstrates the key role of 3-deoxypentos-2-ulose as an intermediate in the formation of 4a/4b. Reaction pathways leading to the colorants 2, 3a/3b, and 4a/4b from pentoses and alanine are discussed.