(E)-1-(2'-thienyl)-2-(p-ethynylphenyl)ethene | 743436-38-6

• 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: (E)-1-(2'-thienyl)-2-(p-ethynylphenyl)ethene
• 英文别名: 2-[(E)-2-(4-ethynylphenyl)ethenyl]thiophene
• CAS: 743436-38-6
• 化学式: C₁₄H₁₀S
• 分子量: 210.299
• InChiKey: RYGNZZHLQMHOFO-MDZDMXLPSA-N

物化性质

• 熔点：
  117-119 °C(Solv: hexane (110-54-3))
• 沸点：
  334.1±21.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(2'-thienyl)-2-(p-ethynylphenyl)ethene 在 次溴酸钾 、 盐酸羟胺 、 乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (E,E)-1,4-di(4-(2-(2-thienyl)ethenyl)phenyl)-1,3-butadiyne
  参考文献：
  名称：

  Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties

  摘要：

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.032
• 作为产物：
  描述：

  (4-iodobenzyl)triphenylphosphonium bromide 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 potassium tert-butylate 、 碘 、 二乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 104.5h， 生成 (E)-1-(2'-thienyl)-2-(p-ethynylphenyl)ethene
  参考文献：
  名称：

  Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties

  摘要：

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.032

文献信息

• Synthesis and optical properties of conjugated N,N-dimethyl and thienyl end-capped 2,5-(arylethynyl)thiophene oligomer structures
  作者：J. Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio、Jorge Esquivias

  DOI：10.1016/j.tetlet.2004.07.123

  日期：2004.9

  by the Cl2Pd(PPh3)2/CuI system, in good to excellent yields. The 2,5-di[(3′,5′-di(trimethylsilylethynyl)phenyl]x-1-ethynyl]thiophene oligomers were prepared by heterocoupling between 3′,5′-di[(trimethylsilylethynyl)phenyl]x-1-ethyne (n = 0–2) terminal acetylenes and 2,5-diiodothiophene, in excellent yields. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology

  通过在末端乙炔之间进行杂偶合，合成对位封端的（N，N-二甲基氨基苯基）和2'-噻吩基乙炔基2,5-噻吩低聚物结构：p-（N，N-二甲基氨基苯基）乙炔（3）[或1- （p-（N，N-二甲基氨基苯基）-2- p-（乙炔基苯基）乙炔，4]；p-（β-乙烯基-2'-噻吩基）苯基乙炔（E -9）[或p-（β-乙炔基- Cl 2 Pd（PPh 3）2催化的2'-噻吩基）苯基乙炔11]和2,5-二碘噻吩/ CuI系统，良率至良率。通过3，，5'-二[（三甲基甲硅烷基乙炔基）苯基] x -1-之间的杂合制备2,5-二[（3'，5'-二（三甲基甲硅烷基乙炔基）苯基] x -1-乙炔基]噻吩低聚物乙炔（n  = 0–2）末端乙炔和2,5-二碘噻吩，收率很好。通过特定的保护-脱保护方法有效地制备了末端乙炔。所有获得的乙炔基苯基化合物均显示出荧光辐射发射，红移为随着链共轭增加的波长。
• Synthesis of conjugated 2-arylethynyl and 2-arylethenyl thiophene structures with optical properties
  作者：J.Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tetlet.2004.05.104

  日期：2004.7

  Conjugated mono(arylethynyl)oligothiophene structures have been obtained starting with (E)-[1-(2'-thienyl)-2-(p-phenyl)]ethyne (E)-7 and 2-[p-(iodophenyl)ethynyl]thiophene 8. Conjugated nanostructures were synthesized by oxidative coupling between the terminal acetylenes (E)-7 and 8 to give, respectively, 1,4-di[(2-p-(iodophenyl)ethynyl)thienyl]-1,3-butadiyne and 1,4-di[(2-p-iodophenylethynyl)thienyl]-1,3-butadiyne. All the thiophene derivatives synthesized show an important fluorescence radiation emission, with a bathochromic shift, which increases with the conjugation of the chain. (C) 2004 Elsevier Ltd. All rights reserved.