3,3'-bis(10-methoxycarbonyldecyl)-4,4'-dimethylpyrromethane-5,5'-dicarboxylylic acid | 887499-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,3'-bis(10-methoxycarbonyldecyl)-4,4'-dimethylpyrromethane-5,5'-dicarboxylylic acid
• 英文别名: 5-[[5-carboxy-3-(11-methoxy-11-oxoundecyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-(11-methoxy-11-oxoundecyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 887499-12-9
• 化学式: C₃₇H₅₈N₂O₈
• 分子量: 658.876
• InChiKey: AQARKFRTNNQMMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  47
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carbaldehyde 、 3,3'-bis(10-methoxycarbonyldecyl)-4,4'-dimethylpyrromethane-5,5'-dicarboxylylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到11-[18-(10-methoxycarbonyl-decyl)-3,7,8,13,13,17-hexamethyl-12,13,22,24-tetrahydro-porphin-2-yl]-undecanoic acid methyl ester
  参考文献：
  名称：

  Studies in Chlorin Chemistry. 3. A Practical Synthesis of C,D-Ring Symmetric Chlorins of Potential Utility in Photodynamic Therapy

  摘要：

  C,D-ring symmetric chlorins 8 were prepared in 47-85% yield, on scales up to several hundred milligrams, by condensation of appropriately substituted bis-formyldihydrodipyrrins 6 and dipyrromethane biscarboxylic acids 7 in 5% TFA/CH2Cl2 (25 examples). Target chlorins were chosen to systematically probe the effect of lipophilic and hydrophilic substituents on tissue partitioning and cellular membrane penetration in photodynamic therapy (PDT).

  DOI：

  10.1021/jo060041z
• 作为产物：
  描述：

  4-methoxycarbonyldecyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 3,3'-bis(10-methoxycarbonyldecyl)-4,4'-dimethylpyrromethane-5,5'-dicarboxylylic acid
  参考文献：
  名称：

  Studies in Chlorin Chemistry. 3. A Practical Synthesis of C,D-Ring Symmetric Chlorins of Potential Utility in Photodynamic Therapy

  摘要：

  C,D-ring symmetric chlorins 8 were prepared in 47-85% yield, on scales up to several hundred milligrams, by condensation of appropriately substituted bis-formyldihydrodipyrrins 6 and dipyrromethane biscarboxylic acids 7 in 5% TFA/CH2Cl2 (25 examples). Target chlorins were chosen to systematically probe the effect of lipophilic and hydrophilic substituents on tissue partitioning and cellular membrane penetration in photodynamic therapy (PDT).

  DOI：

  10.1021/jo060041z