2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)ethyl acetate | 1291090-51-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)ethyl acetate
• CAS: 1291090-51-1
• 化学式: C₁₆H₁₄BrNO₄
• 分子量: 364.195
• InChiKey: RGONNUOXXJTVAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.3
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)ethyl acetate 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 6.08h， 生成 tert-butyl 1-(2-acetoxyethyl)-8-(4-(dimethylamino)phenyl)-2-methyl-7-oxopyrano[3,2-e]indole-3(7H)-carboxylate
  参考文献：
  名称：

  Syntheses and characterizations of novel pyrrolocoumarin probes for SNAP-tag labeling technology

  摘要：

  SNAP-tag technology is a revolutionary protein labeling technology employing in various biological studies. Since low signal/noise ratio and severe overlap between the FRET donors/acceptors often occurred in applying present fluorescent probes and thus limited the further applications, development of new fluorescent probes with excellent fluorescent properties is still of request by today's SNAP-tag technology. In this paper, a number of SNAP-tag protein probes have been developed by incorporating a novel pyrrolocoumarin fluorophore recently developed by our group. Examination of these novel synthetic compounds shows all these materials possess satisfactory fluorescent properties. Among these, probe 7 exhibits the most excellent characters, and its quantum yield, maximum emission wavelength and Stocks shift reach to 0.44, 534 nm and 112 nm, respectively. Further analysis of structure-property relationship indicates that the probes with a longer C3-substituted alkyl (such as pentyl) give stronger fluorescence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.075
• 作为产物：
  描述：

  6-amino-3-bromo-2H-chromen-2-one 、 5-羟基-2-戊酮 、 溶剂黄146 在 盐酸 、 sodium nitrite 、 tin(II) chloride dihdyrate 作用下， 以 水 为溶剂， 反应 9.5h， 以20%的产率得到2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)ethyl acetate
  参考文献：
  名称：

  Syntheses and characterizations of novel pyrrolocoumarin probes for SNAP-tag labeling technology

  摘要：

  SNAP-tag technology is a revolutionary protein labeling technology employing in various biological studies. Since low signal/noise ratio and severe overlap between the FRET donors/acceptors often occurred in applying present fluorescent probes and thus limited the further applications, development of new fluorescent probes with excellent fluorescent properties is still of request by today's SNAP-tag technology. In this paper, a number of SNAP-tag protein probes have been developed by incorporating a novel pyrrolocoumarin fluorophore recently developed by our group. Examination of these novel synthetic compounds shows all these materials possess satisfactory fluorescent properties. Among these, probe 7 exhibits the most excellent characters, and its quantum yield, maximum emission wavelength and Stocks shift reach to 0.44, 534 nm and 112 nm, respectively. Further analysis of structure-property relationship indicates that the probes with a longer C3-substituted alkyl (such as pentyl) give stronger fluorescence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.075