3,3'-dimethyl-5-phenyl-1,2,8,9-tetraiododipyrrylmethane | 202057-87-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3,3'-dimethyl-5-phenyl-1,2,8,9-tetraiododipyrrylmethane
• 英文别名: 2-[(4,5-diiodo-3-methyl-1H-pyrrol-2-yl)-phenylmethyl]-4,5-diiodo-3-methyl-1H-pyrrole
• CAS: 202057-87-2
• 化学式: C₁₇H₁₄I₄N₂
• 分子量: 753.93
• InChiKey: OBGFLDKCQITOTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,3'-dimethyl-5-phenyl-1,2,8,9-tetraiododipyrrylmethane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到3,3'-dimethyl-5-phenyl-dipyrrylmethane
  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 、 碘 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 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