1,2-phenylenebis(thiophen-2-ylmethanol) | 146474-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-phenylenebis(thiophen-2-ylmethanol)
• 英文别名: 1,2-phenylenebis(2-thienylmethanol)；[2-[Hydroxy(thiophen-2-yl)methyl]phenyl]-thiophen-2-ylmethanol；[2-[hydroxy(thiophen-2-yl)methyl]phenyl]-thiophen-2-ylmethanol
• CAS: 146474-87-5
• 化学式: C₁₆H₁₄O₂S₂
• 分子量: 302.418
• InChiKey: AXXYTTLJGXMGHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-phenylenebis(thiophen-2-ylmethanol) 在 哌啶 、 劳森试剂 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.5h， 生成 1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene
  参考文献：
  名称：

  Synthetic Approach to and Characterization of a Fullerene-DTBT-Fullerene Triad

  摘要：

  The synthesis of a new fullerene-dithienylbenzo[c]thiophene (DTBT)-fullerene triad is reported. The synthetic approach involves the synthesis of a DTBT unit, a Sonogashira reaction to introduce two acetylenic groups, and the coupling with fullerene. The product showed an absorption at lambda = 485 nm and a fluorescence band at lambda = 575 nm.

  DOI：

  10.1055/s-0032-1316902
• 作为产物：
  描述：

  magnesium,2H-thiophen-2-ide,bromide 、 邻苯二甲醛 以 四氢呋喃 为溶剂， 生成 1,2-phenylenebis(thiophen-2-ylmethanol)
  参考文献：
  名称：

  基于1,3-二（2-噻吩基）苯并[ c ]噻吩的导电聚合物的制备与表征

  摘要：

  由单体1，3-二（2-噻吩基）苯并[ c ]噻吩获得了带隙为1.7eV的电活性聚合物。

  DOI：

  10.1039/c39930000172

文献信息

• Regioselective Annulation of Unsymmetrical 1,2-Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[<i>b</i>]thiophene Analogues
  作者：Ramakrishnan Sivasakthikumaran、Settu Muhammad Rafiq、Elumalai Sankar、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201501087

  日期：2015.12

  A systematic study on the regioselective cyclization of benzene- and naphthalene-based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulation products. By using this method, synthesis of a wide variety of anthracene, tetracene and naphtho[b]thiophene analogues was achieved in good to excellent yields. By employing HBr (33 %) in acetic acid as a catalyst

  一项关于苯和萘基不对称二醇与 HBr (33%) 在室温下在乙酸中的区域选择性环化的系统研究导致形成环化产物。通过使用这种方法，合成了多种蒽、并四苯和萘并[b]噻吩类似物，收率良好至极好。通过在乙酸中使用 HBr (33 %) 作为不对称二醇区域选择性环化的催化剂，非常容易并且避免了常见的二氢异苯并呋喃形成。
• Improved Synthesis of Aryl-Substituted Anthracenes and Heteroacenes
  作者：Guijie Li、Shaolin Zhou、Guowei Su、Yuanhong Liu、Peng George Wang

  DOI：10.1021/jo7017334

  日期：2007.12.1

  [Graphics]A Bronsted acid-catalyzed highly efficient construction,of substituted arylanthracenes and heteroacenes is described, which is assumed to be initiated through the facile formation of a benzylic cation intermediate. This method offers several advantages in comparison with known aromatic cyclodehydration reactions such as high selectivities, mild reaction conditions, and easily accessible starting materials.
• Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.3987/com-14-13145

  日期：——

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.
• Preparation and characterization of conducting polymers based on 1,3-di(2-thienyl)benzo [c]thiophene
  作者：S. Musmanni、J. P. Ferraris

  DOI：10.1039/c39930000172

  日期：——

  An electroactive polymer with a bandgap of 1.7 eV has been obtained from the monomer 1,3-di(2-thienyl)benzo[c]thiophene.

  由单体1，3-二（2-噻吩基）苯并[ c ]噻吩获得了带隙为1.7eV的电活性聚合物。
• Synthetic Approach to and Characterization of a Fullerene-DTBT-Fullerene Triad
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.1055/s-0032-1316902

  日期：——

  The synthesis of a new fullerene-dithienylbenzo[c]thiophene (DTBT)-fullerene triad is reported. The synthetic approach involves the synthesis of a DTBT unit, a Sonogashira reaction to introduce two acetylenic groups, and the coupling with fullerene. The product showed an absorption at lambda = 485 nm and a fluorescence band at lambda = 575 nm.