2-(1-hydroxypropan-2-yl)-9-phenyl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one | 1053216-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(1-hydroxypropan-2-yl)-9-phenyl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one
• 英文别名: 2-(1-hydroxypropan-2-yl)-4-phenyl-3H-pyrrolo[3,4-b]indolizin-1-one
• CAS: 1053216-76-4
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: IELXDGUCZOVVOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxypropan-2-yl)-9-phenyl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-(3-oxo-9-phenyl-1H-pyrrolo[3,4-β]indolizin-2(3H)-yl)propyl methanesulfonate
  参考文献：
  名称：

  Combinatorial Discovery of Full-Color-Tunable Emissive Fluorescent Probes Using a Single Core Skeleton, 1,2-Dihydropyrrolo[3,4-β]indolizin-3-one

  摘要：

  We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.

  DOI：

  10.1021/ja8020268
• 作为产物：
  描述：

  2-(1-(tert-butyldimethylsilyloxy)propan-2-yl)-9-phenyl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one 在 氟化氢吡啶 、 甲氧基三甲基硅烷 作用下， 以 四氢呋喃 为溶剂， 生成 2-(1-hydroxypropan-2-yl)-9-phenyl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one
  参考文献：
  名称：

  Combinatorial Discovery of Full-Color-Tunable Emissive Fluorescent Probes Using a Single Core Skeleton, 1,2-Dihydropyrrolo[3,4-β]indolizin-3-one

  摘要：

  We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.

  DOI：

  10.1021/ja8020268