[8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-yl]-acetic acid | 1291090-36-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: [8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-yl]-acetic acid
• CAS: 1291090-36-2
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: JBEZRYXCMLPZTC-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  671.2±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-yl]-acetic acid 、 6-((4-(氨基甲基)苄基)氧基)-7H-嘌呤-2-胺 在 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 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-2-[8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-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：

  8-[4-(dimethylamino)phenyl]-1,2-dimethylpyrano[3,2-e]indol-7(3H)-one 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 生成 [8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-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