3,4-dimethyl-2-hydroxymethyl-pyrrole-5-carboxylic acid | 168066-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-dimethyl-2-hydroxymethyl-pyrrole-5-carboxylic acid
• 英文别名: 5-hydroxymethyl-3,4-dimethylpyrrole-2-carboxylic acid；5-hydroxymethyl-3,4-dimethyl-pyrrole-2-carboxylic acid；5-Hydroxymethyl-3,4-dimethyl-pyrrol-2-carbonsaeure；3,4-Dimethyl-5-hydroxymethyl-pyrrol-2-carbonsaeure；5-(hydroxymethyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid
• CAS: 168066-32-8
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: KOTOXKFTPGLMRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-2-hydroxymethyl-pyrrole-5-carboxylic acid 在 potassium hexacyanoferrate(III) 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以17%的产率得到2,3,7,8,12,13,17,18-octamethyl-porphyrin
  参考文献：
  名称：

  Rhodium Complex-Catalyzed Reaction of Isonitriles with Carbonyl Compounds:  Catalytic Synthesis of Pyrroles

  摘要：

  [GRAPHICS]Low-valent rhodium complexes are efficient catalysts for the activation of alpha -C-H bond of isonitriles. Addition of isonitriles to carbonyl compounds proceeds under mild and neutral conditions to give the corresponding alpha,beta -unsaturated formamides. Catalytic synthesis of pyrroles can be performed by cyclocondensation of isonitriles with 1,3-dicarbonyl compounds.

  DOI：

  10.1021/ol0069296
• 作为产物：
  描述：

  3,4,5-三甲基吡咯-2-甲基乙酯 在 lead(IV) acetate 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3,4-dimethyl-2-hydroxymethyl-pyrrole-5-carboxylic acid
  参考文献：
  名称：

  Rhodium Complex-Catalyzed Reaction of Isonitriles with Carbonyl Compounds:  Catalytic Synthesis of Pyrroles

  摘要：

  [GRAPHICS]Low-valent rhodium complexes are efficient catalysts for the activation of alpha -C-H bond of isonitriles. Addition of isonitriles to carbonyl compounds proceeds under mild and neutral conditions to give the corresponding alpha,beta -unsaturated formamides. Catalytic synthesis of pyrroles can be performed by cyclocondensation of isonitriles with 1,3-dicarbonyl compounds.

  DOI：

  10.1021/ol0069296

文献信息

• Siedel; Winkler, Justus Liebigs Annalen der Chemie, 1943, vol. 554, p. 162,185
  作者：Siedel、Winkler

  DOI：——

  日期：——
• Bullock et al., Journal of the Chemical Society, 1958, p. 1430,1438
  作者：Bullock et al.

  DOI：——

  日期：——
• The effect of steric hindrance in the synthesis of corrolates via the cobalt catalyzed cyclization of 2-(α-hydroxyalkyl)pyrroles
  作者：Silvia Licoccia、Emanuela Tassoni、Roberto Paolesse、Tristano Boschi

  DOI：10.1016/0020-1693(95)90040-d

  日期：1995.7

  2-(alpha-Hydroxyalkyl)pyrroles react in the presence of cobalt ions leading to the formation of corrolates or porphyrinates as a function of the 2-substituents. The nature of the cyclic tetrapyrrole obtained can be related to the steric hindrance of the substituent present in the starting pyrrole, The presence of cobalt ions is essential to drive the reaction towards the formation of the contracted corrole macroring. When 3-ethyl-4-methyl-2-(alpha-hydroxybenzyl)pyr acid is used as starting material an etio-like cobalt correlate, i.e. with alternate methyl and ethyl groups on the beta-pyrrolic positions, has been obtained as demonstrated by detailed analysis of the NMR spectrum of the complex, A possible reaction pathway explaining the formation of such a species is reported.