4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid | 90923-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid
• 英文别名: 3-(2-carboxy-ethyl)-4-methyl-pyrrole-2,5-dicarboxylic acid；3-(2-Carboxy-aethyl)-4-methyl-pyrrol-2,5-dicarbonsaeure；3-(2-carboxyethyl)-4-methyl-1H-pyrrole-2,5-dicarboxylic acid
• CAS: 90923-49-2
• 化学式: C₁₀H₁₁NO₆
• 分子量: 241.2
• InChiKey: IVBCKSVZRVUBNV-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  573.1±50.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid 在 氢溴酸 作用下， 生成 [4-(2-carboxy-ethyl)-3-methyl-pyrrol-2-yl]-[4-(2-carboxy-ethyl)-3-methyl-pyrrol-2-ylidene]-methane
  参考文献：
  名称：

  Fischer; Lamatsch, Justus Liebigs Annalen der Chemie, 1928, vol. 462, p. 240,243,250

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲基-5-乙氧羰基-3-吡咯丙酸乙酯 在 sodium hydroxide 、 磺酰氯 作用下， 生成 4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid
  参考文献：
  名称：

  Synthesis and unusual properties of expanded bilirubin analogs

  摘要：

  DOI：

  10.1016/s0040-4020(01)85333-3

文献信息

• Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs
  作者：Meiqiang Xie、David A. Lightner

  DOI：10.1016/s0040-4020(01)80362-8

  日期：1993.3

  The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene. These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid beta-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones. Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, H-1-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained. The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.
• Nicolaus et al., Annali di Chimica, 1956, vol. 46, p. 793,800
  作者：Nicolaus et al.

  DOI：——

  日期：——
• Nicolaus; Nicoletti, Annali di Chimica, 1957, vol. 47, p. 87,96
  作者：Nicolaus、Nicoletti

  DOI：——

  日期：——
• Synthesis and unusual properties of expanded bilirubin analogs
  作者：Daniel F. Nogales、D. Timothy Anstine、David A. Lightner

  DOI：10.1016/s0040-4020(01)85333-3

  日期：1994.1
• Fischer; Lamatsch, Justus Liebigs Annalen der Chemie, 1928, vol. 462, p. 240,243,250
  作者：Fischer、Lamatsch

  DOI：——

  日期：——