2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)acetic acid | 1291090-40-8

• 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)acetic acid
• CAS: 1291090-40-8
• 化学式: C₁₄H₁₀BrNO₄
• 分子量: 336.142
• InChiKey: PKHUMZNBXLNUTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.3
• 氢给体数：
  2.0
• 氢受体数：
  3.0

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)acetic acid 在 四(三苯基膦)钯 、 氯化亚砜 、 水 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.5h， 生成 N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-2-[8-(4-dimethylamino-phenyl)-2-methyl-7-oxo-3,7-dihydro-pyrano[3,2-e]indol-1-yl]-acetamide
  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 、 乙酰丙酸 在 盐酸 、 sodium nitrite 、 tin(II) chloride dihdyrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.5h， 以35%的产率得到2-(8-bromo-2-methyl-7-oxo-3,7-dihydropyrano[3,2-e]indol-1-yl)acetic acid
  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