2,5-dicarboxy-3-methyl-1H-pyrrole-4-propanoic acid ethyl ester | 148317-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-dicarboxy-3-methyl-1H-pyrrole-4-propanoic acid ethyl ester
• 英文别名: 3-(3-ethoxy-3-oxopropyl)-4-methyl-1H-pyrrole-2,5-dicarboxylic acid
• CAS: 148317-92-4
• 化学式: C₁₂H₁₅NO₆
• 分子量: 269.254
• InChiKey: LGCHDYCRSSNZOE-UHFFFAOYSA-N

物化性质

• 沸点：
  497.9±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-dicarboxy-3-methyl-1H-pyrrole-4-propanoic acid ethyl ester 在 氢氧化钾 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 25.0~180.0 ℃ 、266.64 Pa 条件下， 反应 5.5h， 生成 1H-吡咯-3-丙酸,5-[(Z)-(3,4-二乙基-1,5-二氢-5-羰基-2H-吡咯-2-亚基)甲基]-4-甲基-
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)80362-8
• 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 、 水 、 三氟乙酸 作用下， 反应 56.0h， 生成 2,5-dicarboxy-3-methyl-1H-pyrrole-4-propanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)80362-8

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.
• 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