2-({2-[(trimethylsilyl)ethynyl]phenyl}ethynyl)aniline | 852619-15-9

• 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: 2-({2-[(trimethylsilyl)ethynyl]phenyl}ethynyl)aniline
• 英文别名: 2-[2-[2-(2-trimethylsilylethynyl)phenyl]ethynyl]aniline
• CAS: 852619-15-9
• 化学式: C₁₉H₁₉NSi
• 分子量: 289.452
• InChiKey: ZLYBHNIKQKQWII-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-({2-[(trimethylsilyl)ethynyl]phenyl}ethynyl)aniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三叔丁基膦 、 四丁基氟化铵 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 2-{[2-({2-[(4-methoxyphenyl)ethynyl]phenyl}ethynyl)phenyl]ethynyl}aniline
  参考文献：
  名称：

  Gold(I)-Catalyzed Polycyclizations of Polyenyne-Type Anilines Based on Hydroamination and Consecutive Hydroarylation Cascade

  摘要：

  A hydroamination-double hydroarylation cascade using aniline derivatives bearing a trienyne moiety as the substrate was efficiently promoted by a gold(I) catalyst to produce benzo[a]naphtho [2,1-c]carbazole derivatives in good yields. This reaction is applicable to various substituted trienyne-type anilines, including 2,3-diethynylthiophene derivatives. The reaction of anilines bearing a tetraenyne and pentaenyne moiety allows direct construction of highly fused carbazoles by tetra- and pentacyclization, respectively, through hydroamination and consecutive hydroarylation without producing any theoretical waste products from the substrates.

  DOI：

  10.1021/jo2018119
• 作为产物：
  描述：

  2-[(三甲基硅基)乙炔基]苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 三乙胺 为溶剂， 反应 18.0h， 生成 2-({2-[(trimethylsilyl)ethynyl]phenyl}ethynyl)aniline
  参考文献：
  名称：

  均相金催化中的CO挤出：通过水与金亚乙烯基的加成反应生成的金酰基物种的反应性

  摘要：

  在这里，我们描述了一种新的金催化的脱羰茚合成。二炔底物的协同σ，π-活化作用可生成亚乙烯基金中间体，该中间体在加水后可转化为酰基金，这是迄今为止几乎没有报道的一种有机金化合物。后者被证明经历了CO的挤出，这是均相金催化完全未知的基本步骤。通过调节起始二炔系统的电子和位阻性质，可以利用这种新的反应性以高收率合成茚衍生物。

  DOI：

  10.1002/anie.201409859

文献信息

• Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[<i>a</i>]carbazoles from Aniline-Substituted Diethynylarenes
  作者：Kimio Hirano、Yusuke Inaba、Toshiaki Watanabe、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1002/adsc.200900880

  日期：2010.2.15

  Aniline-substituted diethynylarenes, which are readily synthesized through Sonogashira coupling reactions from commercially available 1,2-dihaloarenes, directly produce aryl- and heteroaryl-annulated[a]carbazoles by the gold-catalyzed intramolecular cascade hydroamination/cycloisomerization without producing theoretical by-products. This new atom-economical route is easily applicable to various ar

  苯胺取代的二乙炔基很容易通过Sonogashira偶联反应由市售的1,2-二卤代芳烃合成，通过金催化的分子内级联加氢胺化/环异构化反应直接生成芳基和杂芳基环化的[ a ]咔唑，而不会产生理论副产物。 。这种新的原子经济的路线是容易地应用于各种芳基-环[一]咔唑含有烷基，芳基或酯取代基。
• 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.