1,2-bis(2-thienylethynyl)benzene

• 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-bis(2-thienylethynyl)benzene
• 英文别名: 1,2-bis(thiophen-2-ylethynyl)benzene；2-[2-[2-(2-thiophen-2-ylethynyl)phenyl]ethynyl]thiophene
• 化学式: C₁₈H₁₀S₂
• 分子量: 290.409
• InChiKey: IPUNNLBAQDLOML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(2-thienylethynyl)benzene 在 四(三苯基膦)钯 、 碘 、 sodium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 60.0h， 生成 1-[di(thiophen-2-yl)methylene]-2,3-di(thiopen-2-yl)-1H-indene
  参考文献：
  名称：

  Synthesis and Structure of Conjugated Molecules with the Benzofulvene Core

  摘要：

  A general method to synthesize conjugated molecules with a benzofulvene core is reported. Up to four conjugated substituents have been introduced via a three-step sequence including (1) synthesis of 1,2-bis(arylethynyl)benzenes; (2) exo-dig electrophilic cyclization promoted by iodine; and (3) cross-coupling reaction of the resulting bis-iodobenzofulvenes with organoboron, organotin, or ethynyl derivatives under Pd catalysis. Structural aspects of the new compounds are discussed.

  DOI：

  10.1021/ol5015366
• 作为产物：
  描述：

  1,2-二碘苯 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 1,2-bis(2-thienylethynyl)benzene
  参考文献：
  名称：

  Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives

  摘要：

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.062
• 作为试剂：
  描述：

  2-溴吡啶 在 1,2-bis(2-thienylethynyl)benzene 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 19.0h， 生成 2-乙炔基吡啶
  参考文献：
  名称：

  使用atrans-Spanning 1,2-双(2-噻吩基乙炔基)苯配体的无铜Sonogashira偶联反应

  摘要：

  芳基卤化物与末端乙炔的新型无铜 Sonogashira 偶联反应在 1,2-双（2-噻吩基乙炔基）苯 (1) 作为可反式双齿配体的存在下进行。

  DOI：

  10.1246/cl.2011.925

文献信息

• Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene
  作者：Shingo Atobe、Motohiro Sonoda、Yuki Suzuki、Takuya Yamamoto、Haruna Masuno、Hiroyuki Shinohara、Akiya Ogawa

  DOI：10.1007/s11164-012-0654-2

  日期：2013.1

  Palladium-catalyzed oxidative homocoupling of terminal acetylenes, in air, occurred in the presence of 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene as ligand, affording the corresponding conjugated diynes.

  在存在1-（2-吡啶基乙炔基）-2-（2-噻吩基乙炔基）苯作为配体的情况下，钯催化的末端乙炔在空气中的氧化均偶联发生，得到相应的共轭二炔。
• Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives
  作者：Chi-Fong Lin、Yu-Hsiang Lo、Ming-Chu Hsieh、Yi-Hua Chen、Jeh-Jeng Wang、Ming-Jung Wu

  DOI：10.1016/j.bmc.2005.02.062

  日期：2005.5

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of Trifluoromethanesulfanylbenzofulvenes<i>via</i>a Cascade Electrophilic Cyclization under Mild Conditions
  作者：Qing Xiao、Hui Zhu、Guangming Li、Zhiyuan Chen

  DOI：10.1002/adsc.201400561

  日期：2014.12.15

  AbstractThe introduction of the (trifluoromethyl)thio moiety into organic molecules has aroused comprehensive interest recently. We describe herein an efficient and chemoselective synthesis of trifluoromethanesulfanylbenzofulvenes through BiCl3‐ or TsOH‐promoted cascade electrophilic cyclization reactions. The presence of the trifluoromethanesulfanyl cation (CF3S+) would facilitate the electrophilic ring closure and nucleophilic attack of chloride or TsOH. This reaction provides a concise method for the synthesis of chlorine‐ or tosyloxy‐substituted trifluoromethanesulfanylbenzofulvenes in good to excellent yields.magnified image
• Copper-free Sonogashira Coupling Reaction Using a<i>trans</i>-Spanning 1,2-Bis(2-thienylethynyl)benzene Ligand
  作者：Shingo Atobe、Motohiro Sonoda、Yuki Suzuki、Hiroyuki Shinohara、Takuya Yamamoto、Akiya Ogawa

  DOI：10.1246/cl.2011.925

  日期：2011.9.5

  Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl)benzene (1) as a trans-bidentatable ligand.

  芳基卤化物与末端乙炔的新型无铜 Sonogashira 偶联反应在 1,2-双（2-噻吩基乙炔基）苯 (1) 作为可反式双齿配体的存在下进行。
• Synthesis and Structure of Conjugated Molecules with the Benzofulvene Core
  作者：Carmela Martinelli、Antonio Cardone、Vita Pinto、Maurizio Mastropasqua Talamo、Maria Luisa D’arienzo、Ernesto Mesto、Emanuela Schingaro、Fernando Scordari、Francesco Naso、Roberta Musio、Gianluca M. Farinola

  DOI：10.1021/ol5015366

  日期：2014.7.3

  A general method to synthesize conjugated molecules with a benzofulvene core is reported. Up to four conjugated substituents have been introduced via a three-step sequence including (1) synthesis of 1,2-bis(arylethynyl)benzenes; (2) exo-dig electrophilic cyclization promoted by iodine; and (3) cross-coupling reaction of the resulting bis-iodobenzofulvenes with organoboron, organotin, or ethynyl derivatives under Pd catalysis. Structural aspects of the new compounds are discussed.