4-methoxycarbonyldecyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl ester | 887499-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxycarbonyldecyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl ester
• CAS: 887499-27-6
• 化学式: C₂₆H₃₇NO₄
• 分子量: 427.584
• InChiKey: FQWCILLINOAGPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 11-[10-decyl-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：

  乙酰丙酮苄酯 、 methyl 12-acetyl-13-oxo-tetradecanoate 在 溶剂黄146 、 sodium nitrite 、 锌 作用下， 以 水 为溶剂， 反应 12.0h， 以48%的产率得到4-methoxycarbonyldecyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl 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