4-methoxy-4-[2-(trimethylsilyl)ethynyl]benzonitrile | 914106-30-2

• 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: 4-methoxy-4-[2-(trimethylsilyl)ethynyl]benzonitrile
• 英文别名: 4-methoxy-3-[(trimethylsilyl)ethynyl]benzonitrile；4-Methoxy-3-(2-trimethylsilylethynyl)benzonitrile
• CAS: 914106-30-2
• 化学式: C₁₃H₁₅NOSi
• 分子量: 229.354
• InChiKey: ZAWIAIFUHNTRPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-4-[2-(trimethylsilyl)ethynyl]benzonitrile 在 盐酸 、 caesium carbonate 、 三丁基氧化锡 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 、 苯 为溶剂， 反应 120.0h， 生成 3,5-bis[5-(N-isopropylamidino)-2-methoxyphenyl]isoxazole
  参考文献：
  名称：

  Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

  摘要：

  3,5-Bis(4-amidinophenyl)isoxazole (3)an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazoleand 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43 were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

  DOI：

  10.1021/jm0612867
• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲腈 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 反应 3.0h， 以80%的产率得到4-methoxy-4-[2-(trimethylsilyl)ethynyl]benzonitrile
  参考文献：
  名称：

  Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

  摘要：

  3,5-Bis(4-amidinophenyl)isoxazole (3)an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazoleand 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43 were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

  DOI：

  10.1021/jm0612867

文献信息

• Practical, Modular, and General Synthesis of 3-Coumaranones through Gold-Catalyzed Intermolecular Alkyne Oxidation Strategy
  作者：Chao Shu、Rongfu Liu、Shuang Liu、Jian-Qiao Li、Yong-Fei Yu、Qiao He、Xin Lu、Long-Wu Ye

  DOI：10.1002/asia.201403032

  日期：2015.1

  A gold‐catalyzed intermolecular alkyne oxidation for the preparation of 3‐coumaranones has been developed. Using 8‐isopropylquinoline N‐oxides as oxidants, the reactions of o‐ethynylanisoles afford versatile 3‐coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

  已经开发了一种金催化的分子间炔烃氧化方法，用于制备3-香豆素。使用8-异丙基喹啉N-氧化物作为氧化剂，邻乙炔基苯甲醚的反应可提供中等至良好的分离产率的多功能3-香豆醛酮。该化学方法的合成效用还通过天然产物硫酸脂的合成来表明。
• Synthesis of C-linked immobilized analogs of aloisine A by ‘click’ chemistry
  作者：Rose Haddoub、David Gueyrard、Peter G. Goekjian

  DOI：10.1016/j.tetlet.2008.11.051

  日期：2009.2

  An efficient approach for the immobilization of a series of analogs of aloisine A, an in vitro inhibitor of protein kinases, to polymeric supports via a [3+2] cycloaddition reaction is reported. (C) 2008 Elsevier Ltd. All rights reserved.