Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carbaldehyde | 334474-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carbaldehyde
• 英文别名: Z-3,4-dimethyl-5-[phenyl-(4,5,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-methyl]-1H-pyrrole；3,4-dimethyl-5-[(Z)-phenyl-(4,4,5-trimethyl-3H-pyrrol-2-ylidene)methyl]-1H-pyrrole-2-carbaldehyde
• CAS: 334474-33-8
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: VMLNMOCJSQDEBY-ZPHPHTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carbaldehyde 在 吡啶 、 selenium(IV) oxide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 29.25h， 生成 5-[18-(4-methoxycarbonyl-butyl)-3,7,8,13,13,17-hexamethyl-10-phenyl-12,13,22,24-tetrahydro-porphin-2-yl]-pentanoic 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-(4,4-dimethyl-2,5-dioxo-1-phenyl-hexyl)-3,4-dimethyl-1H-pyrrole-2-carbaldehyde 在 aluminum oxide 、 碳酸氢铵 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以37%的产率得到Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-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

文献信息

• A New Synthesis of Chlorins
  作者：Peter A. Jacobi、Sandra Lanz、Indranath Ghosh、Sam H. Leung、Franziska Löwer、Douglas Pippin

  DOI：10.1021/ol006983m

  日期：2001.3.1

  A new synthesis of chlorins has been developed, based upon the acid-catalyzed condensation of dialdehydes AB with dipyrromethanes CD.

  基于二醛AB与二吡咯甲烷CD的酸催化缩合反应，开发了一种新的二氢卟酚合成方法。
• 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).