5-[(5-carboxy-3-methyl-1H-pyrrol-2-yl)-phenylmethyl]-4-methyl-1H-pyrrole-2-carboxylic acid | 202057-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[(5-carboxy-3-methyl-1H-pyrrol-2-yl)-phenylmethyl]-4-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 202057-86-1
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: IIIFWERXWQZRLP-UHFFFAOYSA-N

物化性质

• 沸点：
  637.8±55.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(5-carboxy-3-methyl-1H-pyrrol-2-yl)-phenylmethyl]-4-methyl-1H-pyrrole-2-carboxylic acid 在 碘 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以11.8 g的产率得到3,3'-dimethyl-5-phenyl-1,2,8,9-tetraiododipyrrylmethane
  参考文献：
  名称：

  Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin

  摘要：

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.

  DOI：

  10.1021/jo971807l
• 作为产物：
  描述：

  diethyl 3,7-dimethyl-5-phenyl-1,9-dipyrrylmethanedicarboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-[(5-carboxy-3-methyl-1H-pyrrol-2-yl)-phenylmethyl]-4-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin

  摘要：

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.

  DOI：

  10.1021/jo971807l

文献信息

• Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin
  作者：Aldonia Valasinas、Jorge Hurst、Benjamin Frydman

  DOI：10.1021/jo971807l

  日期：1998.2.1

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.