2-甲巯基-5-频那醇酯噻吩 | 1172999-13-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-甲巯基-5-频那醇酯噻吩
• 英文名称: 4,4,5,5-tetramethyl-2-(5-(methylthio)thiophen-2-yl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-(5-methylsulfanylthiophen-2-yl)-1,3,2-dioxaborolane
• CAS: 1172999-13-1
• 化学式: C₁₁H₁₇BO₂S₂
• 分子量: 256.198
• InChiKey: ADUWWMSFVTWLQY-UHFFFAOYSA-N

物化性质

• 沸点：
  354.8±27.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲巯基-5-频那醇酯噻吩 、 5,6-二氯-2,3-二氰基吡嗪 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以25%的产率得到5,6-bis(5-(methylthio)thiophen-2-yl)pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  双氰基吡嗪的结构设计：朝向具有定制光氧化还原活性的推拉分子†

  摘要：

  作为成功的二氰基吡嗪光氧化还原催化剂的延伸，设计并轻松合成了一系列具有系统改变结构的X形推挽分子；它们的结构-性质关系通过以下方式详细阐明实验和理论计算。双氰基吡嗪被证明是一种强大的光氧化还原催化剂，具有推挽式排列，可以通过互换 D-π-A 系统的特定部分来轻松调整性能。改变氰基受体与甲氧基、甲硫基和噻吩基供体的相互位置以及修饰连接基可以广泛调整催化剂的基本性质。与目前可用的有机光氧化还原催化剂相反，我们提供了一系列基于吡嗪杂环支架的催化剂，具有易于合成和进一步改性、多种光氧化还原特性和在现代光氧化还原转化中的广泛应用潜力。

  DOI：

  10.1039/c9ra04731j
• 作为产物：
  描述：

  2-(甲硫基)噻吩 、 异丙醇频哪醇硼酸酯 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 2-甲巯基-5-频那醇酯噻吩
  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

文献信息

• Structural elaboration of dicyanopyrazine: towards push–pull molecules with tailored photoredox activity
  作者：Zuzana Hloušková、Milan Klikar、Oldřich Pytela、Numan Almonasy、Aleš Růžička、Veronika Jandová、Filip Bureš

  DOI：10.1039/c9ra04731j

  日期：——

  provided a series of catalysts based on a pyrazine heterocyclic scaffold with easy synthesis and further modification, diverse photoredox characteristics and wide application potential across modern photoredox transformations. The photoredox catalytic activities of the target catalysts were examined in a benchmark cross-dehydrogenative coupling and novel and challenging annulation reactions.

  作为成功的二氰基吡嗪光氧化还原催化剂的延伸，设计并轻松合成了一系列具有系统改变结构的X形推挽分子；它们的结构-性质关系通过以下方式详细阐明实验和理论计算。双氰基吡嗪被证明是一种强大的光氧化还原催化剂，具有推挽式排列，可以通过互换 D-π-A 系统的特定部分来轻松调整性能。改变氰基受体与甲氧基、甲硫基和噻吩基供体的相互位置以及修饰连接基可以广泛调整催化剂的基本性质。与目前可用的有机光氧化还原催化剂相反，我们提供了一系列基于吡嗪杂环支架的催化剂，具有易于合成和进一步改性、多种光氧化还原特性和在现代光氧化还原转化中的广泛应用潜力。
• Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells
  作者：Massimo Zambianchi、Francesca Di Maria、Antonella Cazzato、Giuseppe Gigli、Manuel Piacenza、Fabio Della Sala、Giovanna Barbarella

  DOI：10.1021/ja902416s

  日期：2009.8.12

  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.