N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-3-{2-[2-(2-{2-[8-(4-dimethylamino-phenyl)-2-methyl-7-oxo-3,7-dihydro-pyrano[3,2-e]indol-1-yl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionamide | 1291090-30-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-3-{2-[2-(2-{2-[8-(4-dimethylamino-phenyl)-2-methyl-7-oxo-3,7-dihydro-pyrano[3,2-e]indol-1-yl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionamide
• 英文别名: N-[[4-[(2-amino-7H-purin-6-yl)oxymethyl]phenyl]methyl]-3-[2-[2-[2-[2-[8-[4-(dimethylamino)phenyl]-2-methyl-7-oxo-3H-pyrano[3,2-e]indol-1-yl]ethoxy]ethoxy]ethoxy]ethoxy]propanamide
• CAS: 1291090-30-6
• 化学式: C₄₄H₅₀N₈O₈
• 分子量: 818.93
• InChiKey: QEUDIYRROZVGEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  5-羟基-2-戊酮 在 盐酸 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium tert-butylate 、 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 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.08h， 生成 N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-3-{2-[2-(2-{2-[8-(4-dimethylamino-phenyl)-2-methyl-7-oxo-3,7-dihydro-pyrano[3,2-e]indol-1-yl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionamide
  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