5-Ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic acid | 53365-89-2

• 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-Ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic acid
• 英文别名: 5-carboxy-2-(ethoxycarbonyl)-4-ethyl-3-methylpyrrole；3-methyl-4-ethyl-5-carboxy-2-ethoxycarbonylpyrrole；2-carboxy-5-carbethoxy-3-ethyl-4-methylpyrrole；5-carbethoxy-2-carboxy-3-ethyl-4-methylpyrrole；3-ethyl-4-methyl-pyrrole-2,5-dicarboxylic acid 5-ethyl ester；3-Aethyl-4-methyl-pyrrol-2,5-dicarbonsaeure-5-aethylester；5-(Ethoxycarbonyl)-3-ethyl-4-methyl-1H-pyrrole-2-carboxylic acid；5-ethoxycarbonyl-3-ethyl-4-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 53365-89-2
• 化学式: C₁₁H₁₅NO₄
• mdl: MFCD00030412
• 分子量: 225.244
• InChiKey: MKNHWTOENPMOPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-Ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic acid 在 platinum(IV) oxide 、 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 碘 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 、 苯甲醇 为溶剂， 反应 67.75h， 生成 5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-1,9-dicarboxydipyrromethane
  参考文献：
  名称：

  Artificial photosynthetic reaction centers with carotenoid antennas

  摘要：

  Two reaction center-antenna models based on a purpurin macrocycle linked to a C-60 and to a carotenoid polyene have been synthesized. In these systems the C60 Moiety is the primary electron acceptor, the purpurin is the primary electron donor and the carotenoid moiety acts both as an antenna and secondary electron donor. Formation of the initial charge separated state, C-Pur(.+)-C-60(.-) following excitation with light absorbed by either the purpurin or C60 takes place on the 10 ps time scale. The final charge separated state, C.+-Pur-C-60(.-), is formed in one of the compounds with a quantum yield of 32% based upon light absorbed by the carotenoid. In order to function as an antenna, the carotenoid pigment must be electronically coupled to the purpurin. The purpurin C ring provides an excellent framework for locating a carotenoid polyene in partial conjugation with the macrocycle, leading to a relatively strong electronic communication between the chromophores; functionalization of a meso position of the purpurin provides a site for the covalent attachment of C-60 . (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.121
• 作为产物：
  描述：

  4-乙基-3-甲基-5-(三氯甲基)-1H-吡咯-2-甲酸乙酯 以 水 、 丙酮 为溶剂， 以80.2%的产率得到5-Ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  An improved approach to 5'-unsubstituted 5-formyldipyrromethanes

  摘要：

  DOI：

  10.1021/jo00220a030

文献信息

• A new convergent method for porphyrin synthesis based on a ‘3 + 1’ condensation
  作者：Arezki Boudif、Michel Momenteau

  DOI：10.1039/p19960001235

  日期：——

  porphyrins 30 and 31 including an analogue of the corallistin-A and vic-diacrylic ester porphyrins 32 and 34. For this purpose, synthesis of various tripyrranes and pyrrole-2,5-dicarbaldehydes have been reported and characterized. Studies by dynamic 1H NMR of sterically hindered tripyrranes show conformational exchange, in solution. Structures of the new porphyrins have been confirmed by 1H NMR spectrometry

  基于tripyrranes和吡咯-2,5-二甲醛的“3 + 1”的酸催化缩合的新方法已被使用，在第一次，对于两种类型的卟啉的合成：VIC -dipropionic卟啉酯30和31包括corallistin-A的类似物和VIC -diacrylic卟啉酯32和34为此目的，各种tripyrranes和吡咯-2,5- dicarbaldehydes的合成已有报道和表征。通过空间受阻三吡喃的动态1 H NMR研究显示溶液中的构象交换。新的卟啉的结构已被1证实。1 H NMR光谱法。在邻位引入二丙烯酸酯基团显着影响化合物32和34的电子光谱，它们呈现出氧杂多型吸收模式。
• Fischer et al., Justus Liebigs Annalen der Chemie, 1930, vol. 480, p. 109,122, 155
  作者：Fischer et al.

  DOI：——

  日期：——
• Mamardashvili, N. Zh.; Semeikin, A. S.; Golubchikov, O. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 6.2, p. 1007 - 1015
  作者：Mamardashvili, N. Zh.、Semeikin, A. S.、Golubchikov, O. A.

  DOI：——

  日期：——
• Siedel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 231, p. 167,184
  作者：Siedel

  DOI：——

  日期：——
• Fischer; Sturm; Friedrich, Justus Liebigs Annalen der Chemie, 1928, vol. 461, p. 250,263
  作者：Fischer、Sturm、Friedrich

  DOI：——

  日期：——