5-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carbaldehyde | 887499-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• 英文别名: 5-[(E)-(4,4-dimethyl-5-oxooxolan-2-ylidene)methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 887499-20-9
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: QPPZOJPZYHZGCA-BJMVGYQFSA-N

物化性质

• 熔点：
  166.8-167.5 °C
• 沸点：
  443.5±45.0 °C(predicted)
• 密度：
  1.206±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carbaldehyde 在 aluminum oxide 、 碳酸氢铵 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 1.33h， 生成 Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-methyl]-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
• 作为产物：
  描述：

  原甲酸三乙酯 、 tert-butyl 5-[(E)-(4,4-dimethyl-5-oxooxolan-2-ylidene)methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate 在 三氟乙酸 作用下， 反应 0.5h， 以95%的产率得到5-(4,4-dimethyl-5-oxo-dihydro-furan-2-ylidenemethyl)-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).