ethyl 5-formyl-4-methylpyrrole-3-propionate | 36852-28-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 5-formyl-4-methylpyrrole-3-propionate
• 英文别名: ethyl 3-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoate
• CAS: 36852-28-5
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: TYNKCHSADCEWEH-UHFFFAOYSA-N

物化性质

• 沸点：
  339.7±42.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-formyl-4-methylpyrrole-3-propionate 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.58h， 生成 10,10-dimethylglaucorubin
  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-carboxy-5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-propionic acid ethyl ester 在 sodium hydroxide 、 三氟乙酸 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 25.0~180.0 ℃ 、266.64 Pa 条件下， 反应 56.0h， 生成 ethyl 5-formyl-4-methylpyrrole-3-propionate
  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

• The total synthesis of chlorophyll a
  作者：Robert Burns Woodward、William A. Ayer、John M. Beaton、Friedrich Bickelhaupt、Raymond Bonnett、Paul Buchschacher、Gerhard L. Closs、Hans Dutler、John Hannah、Fred P. Hauck、Shǒ Itǒ、Albert Langemann、Eugene Le Goff、Willy Leimgruber、Walter Lwowski、Jürgen Sauer、Zdenek Valenta、Heinrich Volz

  DOI：10.1016/0040-4020(90)80003-z

  日期：1990.1

  The total synthesis of chlorophyll a starting from Knorr's pyrrole (1) is described with full experimental detail. Forty six stages are involved to reach the target molecule, chlorin e6 trimethyl ester (46), from which the preparation of chlorophyll a has already been described.

  详细描述了从克诺尔吡咯（1）开始的叶绿素a的总合成。涉及到达到目标分子的四阶段是二氢卟酚e 6三甲基酯（46），从中已经描述了叶绿素a的制备。