2,8-bis(2-hydroxyethyl)-3,7-dimethyl-5-phenyl-1,9-diformyldipyrrylmethane | 202058-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,8-bis(2-hydroxyethyl)-3,7-dimethyl-5-phenyl-1,9-diformyldipyrrylmethane
• 英文别名: 5-[[5-formyl-4-(2-hydroxyethyl)-3-methyl-1H-pyrrol-2-yl]-phenylmethyl]-3-(2-hydroxyethyl)-4-methyl-1H-pyrrole-2-carbaldehyde
• CAS: 202058-01-3
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: NKSGPUCWEUDRCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2,8-bis(2-hydroxyethyl)-3,7-dimethyl-5-phenyl-1,9-diformyldipyrrylmethane 在 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 76.0h， 生成
  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：

  dimethyl 2,8-bis(methoxycarbonylmethyl)-3,7-dimethyl-5-phenyl-1,9-dipyrrylmethanedicarboxylate 在 氢氧化钾 、 diborane(6) 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 三氟乙酸 为溶剂， 反应 28.25h， 生成 2,8-bis(2-hydroxyethyl)-3,7-dimethyl-5-phenyl-1,9-diformyldipyrrylmethane
  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.