2,3-二乙炔基苯并[b]噻吩 | 198693-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2,3-二乙炔基苯并[b]噻吩
• 英文名称: 2,3-diethynylbenzo[b]thiophene
• 英文别名: 2,3-Diethynyl-1-benzothiophene
• CAS: 198693-61-7
• 化学式: C₁₂H₆S
• 分子量: 182.246
• InChiKey: MOVXTQWXFWJCER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 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：

  2,3-二乙炔基苯并[b]噻吩 在 氢碘酸 、 platinum(II) chloride 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到4-碘二苯并噻吩
  参考文献：
  名称：

  Regioselective Haloaromatization of 1,2-Bis(ethynyl)benzene via Halogen Acids and PtCl₂. Platinum-Catalyzed 6-π Electrocyclization of 1,2-Bis(1‘-haloethenyl)benzene Intermediates

  摘要：

  Treatment of 1,2-bis(ethynyl)benzene (1) with aqueous HX (X = Br, I) in hot 3-pentanone (100105 degrees C, 2 h) afforded 1,2-bis(1'-baloethenyl)benzene species 2-Br and 2-I in 98% and 95% yields, respectively. The hydrochlorination of endiyne 1 failed to proceed at elevated temperature but was implemented efficiently by PtCl2 (5 mol %) in hot 3-pentanone (100 degrees C, 2 h) to give 1,2-bis(1'-chloroethenyl)benzene 2-Cl in 80% yield. In the presence of PtCl2 (5 mol %), these halides 2-Cl, 2-Br, and 2-I were subsequently converted to 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in the mother solution via sequential 6-pi electrocyclization and dehalogenation reactions. PtCl2 (5 mol %) also effected direct haloaromatization of endiyne 1 with HX (X = Cl, Br, 1) and gave 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in 64-71% yields. This investigation reports the scope and the regioselectivity of haloaromatization of various enediynes catalyzed by PtCl2.

  DOI：

  10.1021/jo0518295
• 作为产物：
  描述：

  2,3-二溴苯并[b]噻吩 在 potassium carbonate 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 72.0h， 生成 2,3-二乙炔基苯并[b]噻吩
  参考文献：
  名称：

  烯炔和二炔基芳烃单体的热解合成聚苯衍生物

  摘要：

  描述了使用Pd-或交叉偶联方法的取代烯二炔和二炔炔衍生物的合成。然后将产物加热，得到相应的聚（对苯撑），聚（1,4-萘），聚（苯并[ c]]噻吩和聚（二苯并噻吩）。提供了十五个实例，其基于取代基图案和环化部分显示了聚合过程的范围。使用热重分析法证明了新衍生的聚合物具有极好的热回弹性。通常使用与聚合物重复单元结构相似的小分子的红外数据相关性来确定聚合物的结构。由GCMS分析的二聚中间体的自由基捕获进一步证实了所提出的机理路线。通过监测单体消耗程度相对于聚合物分子量来确定逐步增长的聚合方式。

  DOI：

  10.1016/s0040-4020(97)00977-0

文献信息

• [EN] ETHYNYLBENZOTHIOPHENE PESTICIDES
  申请人：FMC CORPORATION

  公开号：WO1992000672A1

  公开（公告）日：1992-01-23

  (EN) Ethynylbenzothiophene compounds of formula (I) are effective as pesticides, wherein R is selected from (a), (b), (c), (d), (e); R1 is selected from hydrogen, halogen, lower alkyl, lower haloalkyl, and phenylethynyl; R2 is selected from hydrogen, halogen, lower alkyl, lower alkylthio, lower haloalkenyl, haloalkenylthio, phenyl lower alkenyl, formyl, lower alkoxycarbonyl, carboxy lower alkenyl, lower alkoxycarbonyl lower alkenyl, phenyl, 2-thienyl, and methylthien-2-yl; R3 is selected from alkyl, lower trialkylsilyl, lower haloalkyl, hydroxyalkyl, alkylcarbonyl, methylthien-2-yl, 2-thienyl, and benzothien-2-yl; R4 is selected from hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkylthio, lower alkoxycarbonyl, amino, and alkylcarbonylamino; and R5 is selected from hydrogen, lower alkyl and lower haloalkyl.(FR) Composés d'éthynylbenzothiophène de la formule (I), efficaces comme pesticides, dans laquelle R est choisi parmi (a), (b), (c), (d), (e); R1 est choisi parmi hydrogène, halogène, alkyle inférieur, haloalkyle inférieur et phényléthynyle; R2 est choisi parmi hydrogène, halogène, alkyle inférieur, alkylthio inférieur, haloalkylkényle inférieur, haloalkénylthio, alkényle inférieur de phényle, formyle, alkoxycarbonyle inférieur, alkényle inférieur de carboxy, alkényle inférieur d'alkoxycarbonyle inférieur, phényle, 2-thiényle, et méthylthién-2-yle; R3 est choisi parmi alkyle, trialkylsilyle inférieur, haloalkyle inférieur, hydroxyalkyle, alkylarbonyle, méthylthién-2-yle, 2-thiényle et benzothién-2-yle; R4 est choisi parmi hydrogène, halogène, alkyle inférieur, haloalkyle inférieur, alkoxy inférieur, haloalkylthio inférieur, alkoxycarbonyle inférieur, amino et alkylcarbonylamino et R5 est choisi parmi hydrogène, alkyle inférieur et haloalkyle inférieur.
• Synthesis of polyphenylene derivatives by thermolysis of enediynes and dialkynylaromatic monomers
  作者：Jens A John、James M Tour

  DOI：10.1016/s0040-4020(97)00977-0

  日期：1997.11

  Described are the syntheses of substituted enediynes and dialkynylaromatics using Pd- or cross coupling procedures. The products were then thermalized to afford the corresponding poly(p-phenylene)s, poly(1,4-naphthalene)s, poly(benzo[c]thiophene)s, and poly(dibenzothiophene)s. Fifteen examples are provided that show the scope of the polymerization process based upon substituent patterns and cyclization

  描述了使用Pd-或交叉偶联方法的取代烯二炔和二炔炔衍生物的合成。然后将产物加热，得到相应的聚（对苯撑），聚（1,4-萘），聚（苯并[ c]]噻吩和聚（二苯并噻吩）。提供了十五个实例，其基于取代基图案和环化部分显示了聚合过程的范围。使用热重分析法证明了新衍生的聚合物具有极好的热回弹性。通常使用与聚合物重复单元结构相似的小分子的红外数据相关性来确定聚合物的结构。由GCMS分析的二聚中间体的自由基捕获进一步证实了所提出的机理路线。通过监测单体消耗程度相对于聚合物分子量来确定逐步增长的聚合方式。
• Regioselective Haloaromatization of 1,2-Bis(ethynyl)benzene via Halogen Acids and PtCl₂. Platinum-Catalyzed 6-π Electrocyclization of 1,2-Bis(1‘-haloethenyl)benzene Intermediates
  作者：Ching-Yu Lo、Manyam Praveen Kumar、Hsu-Kai Chang、Shie-Fu Lush、Rai-Shung Liu

  DOI：10.1021/jo0518295

  日期：2005.12.1

  Treatment of 1,2-bis(ethynyl)benzene (1) with aqueous HX (X = Br, I) in hot 3-pentanone (100105 degrees C, 2 h) afforded 1,2-bis(1'-baloethenyl)benzene species 2-Br and 2-I in 98% and 95% yields, respectively. The hydrochlorination of endiyne 1 failed to proceed at elevated temperature but was implemented efficiently by PtCl2 (5 mol %) in hot 3-pentanone (100 degrees C, 2 h) to give 1,2-bis(1'-chloroethenyl)benzene 2-Cl in 80% yield. In the presence of PtCl2 (5 mol %), these halides 2-Cl, 2-Br, and 2-I were subsequently converted to 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in the mother solution via sequential 6-pi electrocyclization and dehalogenation reactions. PtCl2 (5 mol %) also effected direct haloaromatization of endiyne 1 with HX (X = Cl, Br, 1) and gave 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in 64-71% yields. This investigation reports the scope and the regioselectivity of haloaromatization of various enediynes catalyzed by PtCl2.