1,3,5-trimethyl-2-((E)-2-(1-methylpyrrol-2-yl)vinyl)pyrrole | 1010696-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3,5-trimethyl-2-((E)-2-(1-methylpyrrol-2-yl)vinyl)pyrrole
• CAS: 1010696-41-9
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: BHGPIZLUKVLKSO-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,3,5-trimethyl-2-((E)-2-(1-methylpyrrol-2-yl)vinyl)pyrrole 、 方酸 以 甲苯 、 正丁醇 为溶剂， 反应 6.0h， 以50%的产率得到
  参考文献：
  名称：

  Assessment of Water-Soluble π-Extended Squaraines as One- and Two-Photon Singlet Oxygen Photosensitizers:  Design, Synthesis, and Characterization

  摘要：

  Singlet oxygen sensitization by organic molecules is a topic of major interest in the development of both efficient photodynamic therapy (PDT) and aerobic oxidations under complete green chemistry conditions. We report on the design, synthesis, biology, and complete spectroscopic characterization (vis-NIR linear and two-photon absorption spectroscopy, singlet oxygen generation efficiencies for both one-and two-photon excitation, electrochemistry, intrinsic dark toxicity, cellular uptake, and subcellular localization) of three classes of innovative singlet oxygen sensitizers pertaining to the family of symmetric squaraine derivatives originating from pi-excessive heterocycles. The main advantage of pi-extended squaraine photosensitizers over the large number of other known photosensitizers is their exceedingly strong two-photon absorption enabling, together with sizable singlet oxygen sensitization capabilities, for their use at the clinical application relevant wavelength of 806 nm. We finally show encouraging results about the dark toxicity and cellular uptake capabilities of water-soluble squaraine photosensitizers, opening the way for clinical small animal PDT trials.

  DOI：

  10.1021/ja075933a
• 作为产物：
  描述：

  1,3,5-Trimethylpyrrole-2-carboxaldehyde 、 <(1-methyl-1H-pyrrol-2-yl)methyl>triphenylphosphonium iodide 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到1,3,5-trimethyl-2-((E)-2-(1-methylpyrrol-2-yl)vinyl)pyrrole
  参考文献：
  名称：

  Assessment of Water-Soluble π-Extended Squaraines as One- and Two-Photon Singlet Oxygen Photosensitizers:  Design, Synthesis, and Characterization

  摘要：

  Singlet oxygen sensitization by organic molecules is a topic of major interest in the development of both efficient photodynamic therapy (PDT) and aerobic oxidations under complete green chemistry conditions. We report on the design, synthesis, biology, and complete spectroscopic characterization (vis-NIR linear and two-photon absorption spectroscopy, singlet oxygen generation efficiencies for both one-and two-photon excitation, electrochemistry, intrinsic dark toxicity, cellular uptake, and subcellular localization) of three classes of innovative singlet oxygen sensitizers pertaining to the family of symmetric squaraine derivatives originating from pi-excessive heterocycles. The main advantage of pi-extended squaraine photosensitizers over the large number of other known photosensitizers is their exceedingly strong two-photon absorption enabling, together with sizable singlet oxygen sensitization capabilities, for their use at the clinical application relevant wavelength of 806 nm. We finally show encouraging results about the dark toxicity and cellular uptake capabilities of water-soluble squaraine photosensitizers, opening the way for clinical small animal PDT trials.

  DOI：

  10.1021/ja075933a