2-硼-5-(二甲基氨基)-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯 | 945493-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-硼-5-(二甲基氨基)-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯
• 英文名称: N-Boc-5-(dimethylamino)indol-2-ylboronic acid
• 英文别名: (1-(tert-butoxycarbonyl)-5-(dimethylamino)-1H-indol-2-yl)boronic acid；[5-(dimethylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid
• CAS: 945493-49-2
• 化学式: C₁₅H₂₁BN₂O₄
• 分子量: 304.154
• InChiKey: KQJRUICWEPXFIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  488.7±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-硼-5-(二甲基氨基)-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯 在 palladium diacetate sodium carbonate 、 tppts 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 N,N,N-trimethyl-10-(2-deoxy-β-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dion-3-ammonium iodide
  参考文献：
  名称：

  Fluorescent Pyrimidopyrimidoindole Nucleosides:  Control of Photophysical Characterizations by Substituent Effects

  摘要：

  10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC(PPI)) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dC(PPI) derivatives tested, the trimethylammonium derivative of dC(PPI) was found to emit the brightest fluorescent light. The solvatochromism of dC(PPI) and its derivatives was also studied. Some of the dC(PPI) derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.

  DOI：

  10.1021/jo070206j
• 作为产物：
  描述：

  N,N-二甲基-1H-吲哚-5-胺 在 4-二甲氨基吡啶 、 硼酸三异丙酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-硼-5-(二甲基氨基)-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯
  参考文献：
  名称：

  Fluorescent Pyrimidopyrimidoindole Nucleosides:  Control of Photophysical Characterizations by Substituent Effects

  摘要：

  10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC(PPI)) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dC(PPI) derivatives tested, the trimethylammonium derivative of dC(PPI) was found to emit the brightest fluorescent light. The solvatochromism of dC(PPI) and its derivatives was also studied. Some of the dC(PPI) derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.

  DOI：

  10.1021/jo070206j

文献信息

• Fluorescent Pyrimidopyrimidoindole Nucleosides:  Control of Photophysical Characterizations by Substituent Effects
  作者：Masahiro Mizuta、Kohji Seio、Kenichi Miyata、Mitsuo Sekine

  DOI：10.1021/jo070206j

  日期：2007.7.1

  10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC(PPI)) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dC(PPI) derivatives tested, the trimethylammonium derivative of dC(PPI) was found to emit the brightest fluorescent light. The solvatochromism of dC(PPI) and its derivatives was also studied. Some of the dC(PPI) derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.