5,5'-dibromo-3-methoxy-2,2'-bithiophene | 1404166-44-4

• 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: 5,5'-dibromo-3-methoxy-2,2'-bithiophene
• 英文别名: 5-Bromo-2-(5-bromothiophen-2-yl)-3-methoxythiophene；5-bromo-2-(5-bromothiophen-2-yl)-3-methoxythiophene
• CAS: 1404166-44-4
• 化学式: C₉H₆Br₂OS₂
• 分子量: 354.086
• InChiKey: HQBUQNXCRMSBAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-3-methoxy-2,2'-bithiophene 在 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成
  参考文献：
  名称：

  Outside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones

  摘要：

  硫代噻吩基杂苯醌的基态特性取决于分子骨架上取代基的性质和位置。

  DOI：

  10.1039/c4cp05748a
• 作为产物：
  描述：

  2-bromo-3-methoxythiophene 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 magnesium 作用下， 生成 5,5'-dibromo-3-methoxy-2,2'-bithiophene
  参考文献：
  名称：

  Outside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones

  摘要：

  硫代噻吩基杂苯醌的基态特性取决于分子骨架上取代基的性质和位置。

  DOI：

  10.1039/c4cp05748a

文献信息

• Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups
  作者：Eleonora V. Canesi、Daniele Fazzi、Letizia Colella、Chiara Bertarelli、Chiara Castiglioni

  DOI：10.1021/ja3072385

  日期：2012.11.21

  A series of quinoidal bithiophenes (QBTs) with controlled variations in steric hindrance and electron activity of the substituents has been synthesized. Evidence of their quinoidal versus biradicaloid ground state electronic character has been experimentally detected and coherently identified as fingerprints by spectroscopic methods such as NMR, UV-vis, multiwavelength Raman. From this analysis, alkoxy groups have been shown to strongly affect the electronic structure and the ground-state energy and stability of QBTs. Quantum-chemical calculations correctly predict the experimental spectroscopic response, even while changing the alkyl on phenone from a tertiary carbon atom to secondary to primary toward an unsubstituted phenone, further confirming the validity of the approach proposed. A control of the electronic structure accompanied by negligible variations of the optical gap of the molecules has thus been demonstrated, extending the potential use of quinoidal species in fields ranging from photon harvesting to magnetic applications.
• Outside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones
  作者：L. Colella、L. Brambilla、V. Nardone、E. Parisini、C. Castiglioni、C. Bertarelli

  DOI：10.1039/c4cp05748a

  日期：——

  The character of the ground state of thiophene-based heterophenoquinones depends on the nature and position of substituents on the molecular skeleton.

  硫代噻吩基杂苯醌的基态特性取决于分子骨架上取代基的性质和位置。