4-乙基-5-(羟基甲基)-3-甲基-1H-吡咯-2-羧酸 | 31840-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-乙基-5-(羟基甲基)-3-甲基-1H-吡咯-2-羧酸
• 英文名称: 4-Ethyl-5-hydroxymethyl-3-methyl-pyrrol-2-carbonsaeure
• 英文别名: 4-ethyl-5-(hydroxymethyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 31840-13-8
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: KUQBWVKJYBNIQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  三苯基膦 、 cobalt(II) acetate 、 4-乙基-5-(羟基甲基)-3-甲基-1H-吡咯-2-羧酸 在 sodium acetate 作用下， 以 乙醇 、 三氟乙酸 为溶剂， 以21%的产率得到[(triphenylphosphine)(2,7,12,17-tetramethyl-3,8,13,18-tetraethylcorrolato)cobalt(III)]
  参考文献：
  名称：

  The effect of steric hindrance in the synthesis of corrolates via the cobalt catalyzed cyclization of 2-(α-hydroxyalkyl)pyrroles

  摘要：

  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.

  DOI：

  10.1016/0020-1693(95)90040-d
• 作为产物：
  描述：

  4-乙基-3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 lead(IV) acetate 、 氢氧化钾 、 溶剂黄146 作用下， 生成 4-乙基-5-(羟基甲基)-3-甲基-1H-吡咯-2-羧酸
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Jeandon, C.; Callot, H. J., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 625 - 629
  作者：Jeandon, C.、Callot, H. J.

  DOI：——

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

  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.