4,4,5,5-tetramethyl-2-[5'-(methylthio)-2,2'-bithiophen-5-yl]-1,3,2-dioxaborolane | 1172999-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,4,5,5-tetramethyl-2-[5'-(methylthio)-2,2'-bithiophen-5-yl]-1,3,2-dioxaborolane
• CAS: 1172999-14-2
• 化学式: C₁₅H₁₉BO₂S₃
• 分子量: 338.324
• InChiKey: VLRRDOJLSIGWQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-2-[5'-(methylthio)-2,2'-bithiophen-5-yl]-1,3,2-dioxaborolane 、 5-bromothiophene-2-carboxylic acid 4-sulfo-2,3,5,6-tetrafluorophenyl ester, sodium salt 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以76%的产率得到5''-(methylthio)-2,2':5',2''-terthiophene-5-carboxylic acid 4-sulfo-2,3,5,6-tetrafluorophenyl ester, sodium salt
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells

  摘要：

  We report the expedient microwave-assisted synthesis of thiophene based 4-sulfo-2,3,5,6,tetrafluorophenyl esters whose molecular structure was engineered to achieve blue to red bright fluorescence. The reactivity toward monoclonal antibodies of the newly synthesized fluorophores was analyzed in comparison with that of the corresponding A succinimidyl esters. Single-fluorophore and multiple-fluorophore labeled antibodies were easily prepared with both types of esters. Multiple-fluorophore labeling with blue and orange emitting fluorophores resulted in white fluorescent antibodies. Thiophene based fluorophores displayed unprecedented fluorescence stability in immunostaining experiments. First-principles TD-DFT theoretical calculations helped us to interpret the behavior of fluorescence emission in different environments.

  DOI：

  10.1021/ja902416s
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 5-(methylthio)-2,2'-bithiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 4,4,5,5-tetramethyl-2-[5'-(methylthio)-2,2'-bithiophen-5-yl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells

  摘要：

  We report the expedient microwave-assisted synthesis of thiophene based 4-sulfo-2,3,5,6,tetrafluorophenyl esters whose molecular structure was engineered to achieve blue to red bright fluorescence. The reactivity toward monoclonal antibodies of the newly synthesized fluorophores was analyzed in comparison with that of the corresponding A succinimidyl esters. Single-fluorophore and multiple-fluorophore labeled antibodies were easily prepared with both types of esters. Multiple-fluorophore labeling with blue and orange emitting fluorophores resulted in white fluorescent antibodies. Thiophene based fluorophores displayed unprecedented fluorescence stability in immunostaining experiments. First-principles TD-DFT theoretical calculations helped us to interpret the behavior of fluorescence emission in different environments.

  DOI：

  10.1021/ja902416s