5''-Formyl-3,4,3',4',3'',4''-hexamethyl-1H,1'H,1''H-[2,2';5',2'']terpyrrole-5-carboxylic acid ethyl ester | 199274-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5''-Formyl-3,4,3',4',3'',4''-hexamethyl-1H,1'H,1''H-[2,2';5',2'']terpyrrole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 5-[5-(5-formyl-3,4-dimethyl-1H-pyrrol-2-yl)-3,4-dimethyl-1H-pyrrol-2-yl]-3,4-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 199274-08-3
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: DJHSSYMNPVDJFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4,3',4',3'',4''-hexamethyl-1H,1'H,1''H-[2,2';5',2'']tetrapyrrole-5-carboxylic acid ethyl ester 、 5''-Formyl-3,4,3',4',3'',4''-hexamethyl-1H,1'H,1''H-[2,2';5',2'']terpyrrole-5-carboxylic acid ethyl ester 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到bis(2-(ethoxycarbonyl)-3,4,3',4',3'',4''-hexamethyl-5,2':5',2''-terpyrrole-5'-yl)methene
  参考文献：
  名称：

  5,10,20,25,35,40-Hexanornonapyrrin:  The Largest Structurally Characterized Oligopyrrole Prepared to Date

  摘要：

  The synthesis and X-ray diffraction-based characterization of a nonapyrrolic oligomer 2 [5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole] is reported. It was prepared by condensing 2 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (9). A similar procedure, involving the condensation of 1 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrole (10) was found to give rise to the corresponding hexameric system 4 bis(2-(ethoxycarbonyl)-3,3,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)methene, a system that was likewise characterized by X-ray diffraction methods. It was also found that replacing the monoformyl terpyrrole 8 by the corresponding bipyrrole, namely 2-(ethoxycarbonyl)-2'-formyl-3,4,3',4'-tetramethyl-5,5'-bipyrrole (13), and condensing 2 equiv of it with 1 equiv of 9 gives rise to the heptapyrrole 5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4'-tetramethyl-5,2'-bipyrrol-5'-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (3).

  DOI：

  10.1021/jo971430j
• 作为产物：
  描述：

  3,4,3',4',3'',4''-Hexamethyl-1H,1'H,1''H-[2,2';5',2'']terpyrrole-5,5''-dicarboxylic acid diethyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 三氟乙酸 为溶剂， 反应 19.5h， 生成 5''-Formyl-3,4,3',4',3'',4''-hexamethyl-1H,1'H,1''H-[2,2';5',2'']terpyrrole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  5,10,20,25,35,40-Hexanornonapyrrin:  The Largest Structurally Characterized Oligopyrrole Prepared to Date

  摘要：

  The synthesis and X-ray diffraction-based characterization of a nonapyrrolic oligomer 2 [5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole] is reported. It was prepared by condensing 2 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (9). A similar procedure, involving the condensation of 1 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrole (10) was found to give rise to the corresponding hexameric system 4 bis(2-(ethoxycarbonyl)-3,3,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)methene, a system that was likewise characterized by X-ray diffraction methods. It was also found that replacing the monoformyl terpyrrole 8 by the corresponding bipyrrole, namely 2-(ethoxycarbonyl)-2'-formyl-3,4,3',4'-tetramethyl-5,5'-bipyrrole (13), and condensing 2 equiv of it with 1 equiv of 9 gives rise to the heptapyrrole 5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4'-tetramethyl-5,2'-bipyrrol-5'-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (3).

  DOI：

  10.1021/jo971430j

文献信息

• 5,10,20,25,35,40-Hexanornonapyrrin:  The Largest Structurally Characterized Oligopyrrole Prepared to Date
  作者：Pierfrancesco Morosini、Markus Scherer、Sylvie Meyer、Vincent Lynch、Jonathan L. Sessler

  DOI：10.1021/jo971430j

  日期：1997.12.1

  The synthesis and X-ray diffraction-based characterization of a nonapyrrolic oligomer 2 [5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole] is reported. It was prepared by condensing 2 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (9). A similar procedure, involving the condensation of 1 equiv of the 2-(ethoxycarbonyl)-2 ''-formyl-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',5 ''-terpyrrole (8) with 1 equiv of 2-(ethoxycarbonyl)-3,4,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrole (10) was found to give rise to the corresponding hexameric system 4 bis(2-(ethoxycarbonyl)-3,3,3',4',3 '',4 ''-hexamethyl-5,2':5',2 ''-terpyrrol-5 ''-yl)methene, a system that was likewise characterized by X-ray diffraction methods. It was also found that replacing the monoformyl terpyrrole 8 by the corresponding bipyrrole, namely 2-(ethoxycarbonyl)-2'-formyl-3,4,3',4'-tetramethyl-5,5'-bipyrrole (13), and condensing 2 equiv of it with 1 equiv of 9 gives rise to the heptapyrrole 5,5 ''-bis((2-(ethoxycarbonyl)-3,4,3',4'-tetramethyl-5,2'-bipyrrol-5'-yl)vinyl)-3,4,3',4',3 '',4 ''-hexamethyl-2,2':5',2 ''-terpyrrole (3).