5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-undecyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde | 887499-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-undecyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• 英文别名: 5-[(1Z)-1-(5-formyl-4,4-dimethyl-3H-pyrrol-2-ylidene)undecyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 887499-10-7
• 化学式: C₂₅H₃₈N₂O₂
• 分子量: 398.589
• InChiKey: VKBZHSRFOIPAKR-MRCUWXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-undecyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde 、 3,3',4,4'-tetramethyldipyrromethane-5,5'-dicarboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以38%的产率得到5-decyl-2,2,7,8,12,13,17,18-octamethyl-2,3,22,24-tetrahydro-porphine
  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：

  3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydro-pyrrol-2-ylidene)-undecyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester 在 吡啶 、 selenium(IV) oxide 、 氢溴酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.58h， 生成 5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-undecyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
  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

文献信息

• Studies in Chlorin Chemistry. 3. A Practical Synthesis of C,D-Ring Symmetric Chlorins of Potential Utility in Photodynamic Therapy
  作者：William G. O'Neal、William P. Roberts、Indranath Ghosh、Hui Wang、Peter A. Jacobi

  DOI：10.1021/jo060041z

  日期：2006.4.1

  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).