4-(m-tolylethynyl)pyridine | 1435769-89-3

• 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-(m-tolylethynyl)pyridine
• CAS: 1435769-89-3
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: NRTPSMOCKVQHQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(m-tolylethynyl)pyridine 在 potassium permanganate 、 ammonium acetate 、 copper(II) acetate monohydrate 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 生成 4-(2-(2-Fluorophenyl)-4-(m-tolyl)-1H-imidazol-5-yl)pyridine
  参考文献：
  名称：

  Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells

  摘要：

  The p38 alpha mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers for cardiomyogenesis of hESCs, and if there is a correlation between p38 alpha MAPK inhibition and cardiomyogenesis, we designed and synthesized a series of novel tri-substituted imidazoles with a range of p38 alpha MAPK inhibitory activities. Our studies demonstrated that suitably designed analogues of SB203580 can also be inducers of cardiomyogenesis in hESCs and that cell growth is affected by changes in the imidazole structures. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.103
• 作为产物：
  描述：

  3-溴甲基苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 240.0h， 生成 4-(m-tolylethynyl)pyridine
  参考文献：
  名称：

  Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells

  摘要：

  The p38 alpha mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers for cardiomyogenesis of hESCs, and if there is a correlation between p38 alpha MAPK inhibition and cardiomyogenesis, we designed and synthesized a series of novel tri-substituted imidazoles with a range of p38 alpha MAPK inhibitory activities. Our studies demonstrated that suitably designed analogues of SB203580 can also be inducers of cardiomyogenesis in hESCs and that cell growth is affected by changes in the imidazole structures. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.103

文献信息

• A carrier-free and recyclable protocol for the cross-coupling of terminal alkynes with arylboronic acids in H2O/TBAB
  作者：Bo-Xiao Tang、Ren-Yun Kuang、Ji-Wu Wen、Xiang Huang、Zhen-Xing Zhang、Yu-Jun Shen、Jia-Ping Chen、Wen-Ying Wu

  DOI：10.1016/j.tetlet.2019.06.047

  日期：2019.7

  A new and recyclable protocol was developed for Pd(OAc)2-catalyzed the cross-coupling reaction of terminal alkynes with arylboronic acids using environmentally friendly H2O/TBAB as reaction medium. A series of cross-coupling products containing internal acetylenic bond can be obtained with good selectivity and yield. The Pd(OAc)2/H2O/TBAB system was stable in the Sonogashira-type cross-coupling reaction

  开发了一种新的可回收的Pd（OAc）2协议，使用环境友好的H 2 O / TBAB作为反应介质，催化末端炔烃与芳基硼酸的交叉偶联反应。可以获得具有良好选择性和产率的一系列包含内部炔键的交叉偶联产物。Pd（OAc）2 / H 2 O / TBAB体系在Sonogashira型交叉偶联反应中稳定，可以使用至少三个循环，而催化性能却没有显着下降。结果表明，在合成有机化学中，不受支持和可循环使用的系统可以扩展到C C键形成的其他领域。
• Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne
  作者：Qing-Dong Wang、Si-Xuan Zhang、Zhuo-Wen Zhang、Ying Wang、Mengtao Ma、Xue-Qiang Chu、Zhi-Liang Shen

  DOI：10.1021/acs.orglett.2c01800

  日期：2022.7.15

  An efficient Sonogashira coupling of a heterocyclic phosphonium salt with a terminal alkyne via C–P bond cleavage was developed. The reactions proceeded smoothly in the presence of palladium catalyst, copper(I) iodide, and N,N-diisopropylethylamine (DIPEA) in N-methyl-2-pyrrolidone (NMP) at 100 °C for 12 h, producing the corresponding alkynyl-substituted pyridine, quinoline, pyrazine, and quinoxaline

  开发了一种通过 C-P 键断裂将杂环鏻盐与末端炔烃有效的 Sonogashira 偶联。反应在钯催化剂、碘化铜 (I) 和N- , N-二异丙基乙胺 (DIPEA) 的存在下在N-甲基-2-吡咯烷酮 (NMP) 中在 100 °C 下顺利进行 12 h，生成相应的炔基-取代吡啶、喹啉、吡嗪和喹喔啉，产率中等至良好，底物范围广，官能团耐受性广。此外，还可以实现克级合成，该反应可应用于糖类、药物和天然产物（如雌酮、d-吡喃半乳糖、薄荷醇和布洛芬）。