4-((10-bromoanthracen-9-yl)ethynyl)-N-methylaniline | 1374418-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-((10-bromoanthracen-9-yl)ethynyl)-N-methylaniline
• CAS: 1374418-19-5
• 化学式: C₂₃H₁₆BrN
• 分子量: 386.291
• InChiKey: ZSTKRWHBDIFEIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-((10-bromoanthracen-9-yl)ethynyl)-N-methylaniline 、 5-乙炔-2-脱氧尿苷 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以54%的产率得到1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[2-[10-[2-[4-(methylamino)phenyl]ethynyl]anthracen-9-yl]ethynyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Fluorescent nucleosides with ‘on–off’ switching function, pH-responsive fluorescent uridine derivatives

  摘要：

  We synthesized various pH-responsive fluorescent deoxyuridine derivatives (1a-g). These fluorescent nucleosides exhibited distinctive fluorescence at 470-600 nm in aqueous solvents containing methanol only at acidic to neutral pH values. In particular, 1f exhibited strong fluorescence only at pH range of 3.1-7.2 with a pK(a) of 6.1. Such pH-sensitive fluorescent nucleosides can be used as 'on-off' fluorescence switch for monitoring pH change in biological systems, particularly for cancer cell detection. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.092
• 作为产物：
  描述：

  4-碘-N-甲基苯胺 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.33h， 生成 4-((10-bromoanthracen-9-yl)ethynyl)-N-methylaniline
  参考文献：
  名称：

  Fluorescent nucleosides with ‘on–off’ switching function, pH-responsive fluorescent uridine derivatives

  摘要：

  We synthesized various pH-responsive fluorescent deoxyuridine derivatives (1a-g). These fluorescent nucleosides exhibited distinctive fluorescence at 470-600 nm in aqueous solvents containing methanol only at acidic to neutral pH values. In particular, 1f exhibited strong fluorescence only at pH range of 3.1-7.2 with a pK(a) of 6.1. Such pH-sensitive fluorescent nucleosides can be used as 'on-off' fluorescence switch for monitoring pH change in biological systems, particularly for cancer cell detection. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.092