5-[1-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidene)ethyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde | 887498-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[1-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidene)ethyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• 英文别名: 5-[(1E)-1-(4,4-dimethyl-5-oxooxolan-2-ylidene)ethyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 887498-84-2
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: BMJZIDSCCCIISJ-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[1-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidene)ethyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde 在 吡啶 、 aluminum oxide 、 selenium(IV) oxide 、 碳酸氢铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.58h， 生成 3-[18-(2-methoxycarbonyl-ethyl)-3,7,8,10,13,13,17-heptamethyl-12,13,22,24-tetrahydro-porphin-2-yl]-propionic 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：

  5-{1-[4,4-Dimethyl-5-oxo-dihydro-furan-(2E)-ylidene]-ethyl}-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 、 原甲酸三乙酯 在 三氟乙酸 作用下， 反应 0.5h， 以89%的产率得到5-[1-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidene)ethyl]-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