(2RS)-2-(2-formyl-1H-pyrrol-1-yl)propionic acid | 60026-30-4

• 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: (2RS)-2-(2-formyl-1H-pyrrol-1-yl)propionic acid
• 英文别名: 2-(2-formyl-1H-pyrrole-1-yl)propanoic acid；N-(1'-carboxyethyl)-2-formylpyrrole；2-(2-formyl-1H-pyrrol-1-yl)propanoic acid；2-(2-formylpyrrol-1-yl)propanoic acid
• CAS: 60026-30-4
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: UCFYTGMADQFCTL-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: water (7732-18-5))
• 沸点：
  342.9±22.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苄胺 、 (2RS)-2-(2-formyl-1H-pyrrol-1-yl)propionic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到2-{2-[(3,4-dimethoxybenzyl)aminomethyl]-1H-pyrrol-1-yl}propionic acid
  参考文献：
  名称：

  Azacycloalkanes: XXXIX. New Syntheses of 1H-Pyrrole-1-carboxylic acid and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-one derivatives

  摘要：

  New procedures have been developed for the synthesis of alpha-(2-formyl-1H-pyrrol-1-yl)-substituted carboxylic acids, alpha-(2-R-aminomethyl-1H-pyrrol-1-yl)-substituted carboxylic acids, and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-ones on the basis of furfurol and alpha-amino acids.

  DOI：

  10.1134/s1070428009120136
• 作为产物：
  描述：

  ethyl 2-(2'-formylpyrrol-1-yl)propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以56%的产率得到(2RS)-2-(2-formyl-1H-pyrrol-1-yl)propionic acid
  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

• <scp>d</scp>-Galacturonic Acid: A Highly Reactive Compound in Nonenzymatic Browning. 2. Formation of Amino-Specific Degradation Products
  作者：Steffen Wegener、Maria-Anna Bornik、Lothar W. Kroh

  DOI：10.1021/acs.jafc.5b01121

  日期：2015.7.22

  as typical products of nonenzymatic uronic acid browning reactions. 2-(2-Formyl-1H-pyrrole-1-yl)propanoic acid (FPA) and 1-(1-carboxyethyl)-3-hydroxypyridin-1-ium (HPA) were identified as specific reaction products of uronic acids with amine participation like l-alanine. In contrast, the structurally related d-galacturonic acid methyl ester showed less browning activity and degradation under equal

  与其他糖醛酸的类似溶液相比，对d-半乳糖醛酸和1-丙氨酸的水溶液进行pH 3、5和8的热处理导致快速，更强烈的非酶褐变反应，以及还原糖的美拉德反应。糖醛酸的半缩醛环结构对褐变行为和反应途径有很大的影响。除了还原酸（1,2-二羟基-2-环戊烯-1-酮），4,5-二羟基-2-环戊烯-1-酮（DHCP），呋喃-2-甲醛和正丁烷醇（4-羟基-5） -甲基-3-（2 H）-呋喃酮）可以检测为非酶性糖醛酸褐变反应的典型产物。2-（2-甲酰基-1 H-吡咯-1-基）丙酸（FPA）和1-（1-羧乙基）-3-羟基吡啶-1-鎓（HPA）被确定为具有胺参与的糖醛酸的特异性反应产物，如1-丙氨酸。相反，在相同的反应条件下，与结构相关的d-半乳糖醛酸甲酯显示较少的褐变活性和降解。发现了果胶特异性降解产物，例如5-甲酰基-2-呋喃甲酸和2-呋喃甲酸，但不能单独对d-半乳糖醛酸单体进行验证。
• US3996940A
  申请人：——

  公开号：US3996940A

  公开（公告）日：1976-12-14
• US4122260A
  申请人：——

  公开号：US4122260A

  公开（公告）日：1978-10-24
• US4180660A
  申请人：——

  公开号：US4180660A

  公开（公告）日：1979-12-25
• Azacycloalkanes: XXXIX. New Syntheses of 1H-Pyrrole-1-carboxylic acid and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-one derivatives
  作者：G. V. Mokrov、A. M. Likhosherstov、V. S. Troitskaya、T. A. Gudasheva

  DOI：10.1134/s1070428009120136

  日期：2009.12

  New procedures have been developed for the synthesis of alpha-(2-formyl-1H-pyrrol-1-yl)-substituted carboxylic acids, alpha-(2-R-aminomethyl-1H-pyrrol-1-yl)-substituted carboxylic acids, and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-ones on the basis of furfurol and alpha-amino acids.