5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-1,9-dicarboxydipyrromethane | 881900-81-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-1,9-dicarboxydipyrromethane
• 英文别名: 5-[(5-carboxy-3-ethyl-4-methyl-1H-pyrrol-2-yl)-(4-methoxycarbonylphenyl)methyl]-4-ethyl-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 881900-81-8
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: VTAITIZNMLTQHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-1,9-dicarboxydipyrromethane 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 3,7,13,17-tetraethyl-5-(4-hydroxymethylphenyl)-2,8,12,18-tetramethylporphyrin
  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：

  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