5'-(4-phenylcyclohex-1-en-1-yl)-2,2'-bithiophene-5-carbonitrile

• 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: 5'-(4-phenylcyclohex-1-en-1-yl)-2,2'-bithiophene-5-carbonitrile
• 化学式: C₂₁H₁₇NS₂
• 分子量: 347.505
• InChiKey: AXXKPTXIWFDLNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-iodo-2,2'-bithiophene 在 吡啶 、 盐酸羟胺 、 magnesium 、 三氯氧磷 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 5'-(4-phenylcyclohex-1-en-1-yl)-2,2'-bithiophene-5-carbonitrile
  参考文献：
  名称：

  Photophysical properties of thiophenes and 2,2′-bithiophenes containing alicyclic moieties

  摘要：

  A series of novel 1-hydroxycycloalkyl- and cycloalkenylthiophenes (4a-4c, 4e, 6b, 6d, 6e) and bithiophenes (5a-5e, 7b-7e) were synthesized via Grignard reaction. The conditions control in the Grignard reaction allowed to obtain tertiary alcohols or cycloalkenes selectively. The Vilsmeier-Haack formylation of thiophenes and 2,2'-bithiophenes with alicyclic fragment C-4-C-5 results formation of unsaturated aldehydes whereas cycloalkenes C-6 form 5'-formylbithiophenes as the main isomers. The photophysical properties such as absorption and fluorescence spectra were recorded in different solvents, and relative quantum yields of aldehydes (9a, 9b, 11c-11e) and corresponding carbonitriles (13a, 13b, 15c-15e) were measured. The synthesized compounds showed an intense fluorescence in the 400-520 nm range, moderate quantum yields and large Stokes' shifts values. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.09.013

文献信息

• Photophysical properties of thiophenes and 2,2′-bithiophenes containing alicyclic moieties
  作者：Violetta V. Meshkovaya、Alexander V. Yudashkin、Yuri N. Klimochkin

  DOI：10.1016/j.dyepig.2014.09.013

  日期：2015.2

  A series of novel 1-hydroxycycloalkyl- and cycloalkenylthiophenes (4a-4c, 4e, 6b, 6d, 6e) and bithiophenes (5a-5e, 7b-7e) were synthesized via Grignard reaction. The conditions control in the Grignard reaction allowed to obtain tertiary alcohols or cycloalkenes selectively. The Vilsmeier-Haack formylation of thiophenes and 2,2'-bithiophenes with alicyclic fragment C-4-C-5 results formation of unsaturated aldehydes whereas cycloalkenes C-6 form 5'-formylbithiophenes as the main isomers. The photophysical properties such as absorption and fluorescence spectra were recorded in different solvents, and relative quantum yields of aldehydes (9a, 9b, 11c-11e) and corresponding carbonitriles (13a, 13b, 15c-15e) were measured. The synthesized compounds showed an intense fluorescence in the 400-520 nm range, moderate quantum yields and large Stokes' shifts values. (C) 2014 Elsevier Ltd. All rights reserved.