3,3′,4,4′-tetramethoxy-2,2′-bipyrrole-5,5′-dicarbaldehyde | 1501969-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3′,4,4′-tetramethoxy-2,2′-bipyrrole-5,5′-dicarbaldehyde
• 英文别名: 3,3',4,4'-tetramethoxy-[2,2'-bipyrrole]-5,5'-dialdehyde；5-(5-formyl-3,4-dimethoxy-1H-pyrrol-2-yl)-3,4-dimethoxy-1H-pyrrole-2-carbaldehyde
• CAS: 1501969-49-8
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: DQMARQDBKHYSOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3′,4,4′-tetramethoxy-2,2′-bipyrrole-5,5′-dicarbaldehyde 在 四氯化钛 、 copper(l) chloride 、 锌 作用下， 以 四氢呋喃 、 邻二甲苯 为溶剂， 反应 5.0h， 生成 Ni(II)-2,3,6,7,12,13,16,17-octamethoxyporphycne
  参考文献：
  名称：

  β-Octamethoxyporphycenes

  摘要：

  Porphycene with eight methoxy substituents at its beta-positions was synthesized for the first time in three steps from 3,4-dimethoxypyrrole. The presence of methoxy groups increases its hydrophilicity as evident from their increased solubility in methanol. Among its metallo-derivatives, the Pd(II)-complex displays efficient singlet oxygen quantum yield (73%) and hence can be a potentially good photosensitizer for photo-oxidation, DNA cleavage, and photodynamic therapy (PDT).

  DOI：

  10.1021/ol403068j
• 作为产物：
  描述：

  3,4-二甲氧基吡咯 在 三甲基溴硅烷 、 [双(三氟乙酰氧基)碘]苯 、 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 3,3′,4,4′-tetramethoxy-2,2′-bipyrrole-5,5′-dicarbaldehyde
  参考文献：
  名称：

  β-Octamethoxyporphycenes

  摘要：

  Porphycene with eight methoxy substituents at its beta-positions was synthesized for the first time in three steps from 3,4-dimethoxypyrrole. The presence of methoxy groups increases its hydrophilicity as evident from their increased solubility in methanol. Among its metallo-derivatives, the Pd(II)-complex displays efficient singlet oxygen quantum yield (73%) and hence can be a potentially good photosensitizer for photo-oxidation, DNA cleavage, and photodynamic therapy (PDT).

  DOI：

  10.1021/ol403068j

文献信息

• β-Decamethoxysapphyrin and Its <i>N</i>-Benzyl Analogue
  作者：Anup Rana、B. Sathish Kumar、Pradeepta K. Panda

  DOI：10.1021/acs.orglett.5b01306

  日期：2015.6.19

  The synthesis of a highly electron-rich decamethoxysapphyrin and its 27-N-benzyl analogue is reported for the first time. The effects of beta-methoxy and 27-N-benzyl substitution on structure, anion binding, absorption, and electrochemical properties were explored in detail. Upon 27-N-benzyl substitution, counteranion-induced structural deformation arises in the diprotonated state, which could be clearly noticed both in solution H-1 NMR study and solid-state structural analysis. This type of anion-induced structural deformation is noted for the first time in beta-substituted sapphyrins. Further, the free base sapphyrins generate singlet oxygen with moderate efficiency (similar to 42%); hence, they may act as good photosensitizers.