2-(3-carboxypropanoyl)-3,4,5-trimethylpyrrole | 99986-59-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-(3-carboxypropanoyl)-3,4,5-trimethylpyrrole
• 英文别名: 4-oxo-4-(3,4,5-trimethyl-pyrrol-2-yl)-butyric acid；4-Oxo-4-(3,4,5-trimethyl-pyrrol-2-yl)-buttersaeure；4-oxo-4-(3,4,5-trimethyl-1H-pyrrol-2-yl)butanoic acid
• CAS: 99986-59-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: IRUKKODSQVSMCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,4-三甲基-1H-吡咯 在 氢氧化钾 、 乙醚 、 乙基溴化镁 作用下， 生成 2-(3-carboxypropanoyl)-3,4,5-trimethylpyrrole
  参考文献：
  名称：

  Chierici; Serventi, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1278,1280, 1282

  摘要：

  DOI：

文献信息

• Reaction of some diketones with 5-aminolevulinic acid in acid solution
  作者：Anthony R Butler、Sharon D George

  DOI：10.1016/s0040-4020(01)87976-x

  日期：1993.8

  Some 2,4-diketones react with 5-aminolevulinic acid in acid solution to form pyrroles. There are two modes of cyclisation, one leading to the Knorr and the other to the Fischer-Fink product. By a consideration of the products obtained from pentane-, hexane-, 3-methylpentane-, 3-isopropylpentane-, 3,3-dimethylpentane-, 1,1,1-trifluoropentane- 1,1,1,5,5,5-hexafluoro- pentane-2,4-dione and ethyl acetoacetate

  一些2,4-二酮与5-氨基乙酰丙酸在酸性溶液中反应形成吡咯。环化有两种模式，一种通向克诺尔，另一种通向费歇尔·芬克产品。考虑到从戊烷-，己烷-，3-甲基戊烷-，3-异丙基戊烷-，3,3-二甲基戊烷-，1,1,1-三氟戊烷-1,1,1,5,5,5获得的产物-六氟戊烷-2,4-二酮和乙酰乙酸乙酯已对Knorr和Fischer-Fink产品的形成作了一些概括。还研究了5-甲基-5-氨基乙酰丙酸与戊烷和3-甲基戊烷-2,4-二酮的反应。简要讨论了这些研究与5-氨基乙酰丙酸的环状二聚化的相关性。
• Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants
  作者：Jonathan S. Lindsey、Vanampally Chandrashaker、Masahiko Taniguchi、Marcin Ptaszek

  DOI：10.1039/c0nj00716a

  日期：——

  Tetrapyrrole macrocycles (e.g., porphyrins) have long been proposed as key ingredients in the emergence of life, yet plausible routes for forming their essential pyrrole precursor have previously not been identified. Here, the anaerobic reaction of δ-aminolevulinic acid (ALA, 5–240 mM) with 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH, 5–240 mM) in water (pH 5–7) at 25–85 °C for a few hours to a few days affords uroporphyrinogen, which upon chemical oxidation gives uroporphyrin in overall yield of up to 10%. The key intermediate is the α-methoxymethyl-substituted analogue of the pyrrole porphobilinogen (PBG). Reaction of ALA and the decarboxy analogue of 1-AcOH (1-Me) gave coproporphyrinogen (without its biosynthetic precursor uroporphyrinogen as an intermediate); oxidation gave the corresponding coproporphyrin in yields comparable to those for uroporphyrin. In each case a mixture of porphyrin isomers was obtained, consistent with reversible oligopyrromethane formation. The route investigated here differs from the universal extant biosynthetic pathway to tetrapyrrole macrocycles, where uroporphyrinogen (isomer III) – nature's last common precursor to corrins, heme, and chlorophylls – is derived from eight molecules of ALA (via four molecules of PBG). The demonstration of the spontaneous self-organization of eight acyclic molecules to form the porphyrinogen under simple conditions may open the door to the development of a chemical model for the prebiogenesis of tetrapyrrole macrocycles.

  长期以来，四吡咯大环（如卟啉）一直被认为是生命出现的关键因素，但形成其重要吡咯前体的合理途径以前尚未发现。在这里，δ-氨基乙酰丙酸（ALA，5-240 mM）与 5-甲氧基-3-（甲氧基乙酰基）乙酰丙酸（1-AcOH，5-240 mM）在 25-85 °C 的水中（pH 5-7）经过几小时到几天的厌氧反应生成卟啉原。关键的中间体是吡咯卟啉原（PBG）的α-甲氧基甲基取代类似物。ALA 与 1-AcOH 的癸羧类似物（1-Me）反应产生共卟啉原（没有其生物合成前体尿卟啉原作为中间体）；氧化产生相应的共卟啉，其产量与尿卟啉相当。在每种情况下都能得到卟啉异构体的混合物，这与低聚吡咯烷的可逆形成是一致的。这里研究的途径不同于四吡咯大环的普遍现存生物合成途径，在这种途径中，尿卟啉原（异构体 III）--自然界中卟啉、血红素和叶绿素的最后一种常见前体--来自八分子 ALA（通过四分子 PBG）。证明八个无环分子在简单条件下自发自组织形成卟啉原，可能为开发四吡咯大环的前生物生成化学模型打开了大门。