1,1-bis(5-(ethoxycarbonyl)-3,4-dimethyl-2-pyrrolyl)ethene | 156726-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,1-bis(5-(ethoxycarbonyl)-3,4-dimethyl-2-pyrrolyl)ethene
• 英文别名: ethyl 5-[1-(5-ethoxycarbonyl-3,4-dimethyl-1H-pyrrol-2-yl)ethenyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 156726-85-1
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: YWOOLYZTGHFDMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1-bis(5-(ethoxycarbonyl)-3,4-dimethyl-2-pyrrolyl)ethene 生成 13,17-bis(2-(methoxycarbonyl)ethyl)-2,3,5,7,8,12,18-heptamethylporphyrin
  参考文献：
  名称：

  Syntheses, structure, properties and chemistry of 1,1-di(pyrrolyl)ethenes

  摘要：

  2-未取代的吡咯与乙酸酐和氯化锡的反应意外地促进了自缩合，产生对称的二(吡咯基)乙烯作为副产物，产率为 6-10%，但这些 1,1-二(吡咯基)的总产率)使用合理的替代路线可将乙烯含量提高至66%；讨论了 1,1-二(吡咯基)乙烯 2 的结构和化学。

  DOI：

  10.1039/c39940000791
• 作为产物：
  描述：

  3,4-二甲基-1H-吡咯-2-羧酸乙酯 、 乙酸酐 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以12%的产率得到1,1-bis(5-(ethoxycarbonyl)-3,4-dimethyl-2-pyrrolyl)ethene
  参考文献：
  名称：

  Syntheses and Some Chemistry of 1,2- and 1,1-Bis(2-pyrrolyl)ethenes

  摘要：

  trans-1,2-Bis(2-pyrrolyl)ethenes (e.g. 18-20) are prepared by McMurry-type reductive coupling of the corresponding 2-formylpyrroles. The isomeric 1,1-bis(2-pyrrolyl)ethenes (e.g. 24) are prepared as a minor byproduct in the reaction of 2-unsubstituted pyrroles (e.g. 22) with acetic anhydride under Friedel-Crafts conditions; the major product, as expected is the 2-acetylpyrrole 23. However, 5-(chloromethyl)dipyrromethanes (e.g. 35) can be obtained in high yield by reaction of 2-unsubstituted pyrroles 22 with chloroacetaldehyde diethyl acetal, Base-catalyzed elimination of HCl from 35 affords the 1,1-bis(2-pyrrolyl)ethene 24 along with the trans- and cis-1,2-bis(2-pyrrolyl)-ethenes 18 and 36, respectively. Conditions are optimized to afford a 66% yield of the 1,1-bis(2-pyrrolyl)ethene 24. In neutral organic solvents, 1,1-bis(2-pyrrolyl)ethenes exist in the ethene tautomeric form 2, rather than as the corresponding 5-methyldipyrromethene isomer 3; however, under acidic conditions, the 5-methyldipyrromethene salt 38 is observed, and the 5-methyl group undergoes acid-catalyzed exchange in deuterated solvents. 1,1-Bis(2-pyrrolyl)ethenes (e.g. 24) undergo standard chemistry, such as catalytic hydrogenation (Adams catalyst) of the alkene bond (to give 5-methyldipyrromethane 44), Vilsmeier formylation [to give 2-formyl-1,1-bis(2-pyrrolyl)ethene 57], and reaction with Eschenmoser's salt (N,N-dimethyl(methylene)ammonium iodide) [to give 2-((N,N-dimethylamino)methyl)-1,1-bis(2-pyrrolyl)ethene 59]. Both the 5-methyldipyrromethane-1,9-dicarboxylic acid 45 and the 1,1-bis(5-carboxy-3,4-dimethyl-2-pyrrolyl)ethene 53 react with the 1,9-diformyldipyrromethane 46, under standard MacDonald conditions, to give 3,5,8-trimethyl-deuteroporphyrin IX dimethyl ester 47.

  DOI：

  10.1021/jo961582z