4-[2-(4-甲氧基苯基)乙炔基]吡啶 | 13295-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[2-(4-甲氧基苯基)乙炔基]吡啶
• 英文名称: 4-[2-(4-methoxyphenyl)ethynyl]pyridine
• 英文别名: (4-Methoxyphenyl)(4-pyridyl)acetylene；4-[(4-methoxyphenyl)ethynyl]pyridine；4-(p-anisyl)ethynylpyridine；4-(4-methoxy-phenylethynyl)-pyridine；4-(4-Methoxy-phenylaethinyl)-pyridin；4-(2-(4-methoxyphenyl)ethynyl)pyridine
• CAS: 13295-95-9
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: YLGABGCTQMOWDL-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  361.2±22.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

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：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(4-甲氧基苯基)乙炔基]吡啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以54%的产率得到(4-Methoxyphenyl)(4-pyridyl)acetylene N-Oxide
  参考文献：
  名称：

  Synthesis of optically quadratic nonlinear phenylpyridylacetylenes

  摘要：

  DOI：

  10.1021/jo00031a060
• 作为产物：
  描述：

  (4-甲氧基苯乙炔基)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.0h， 生成 4-[2-(4-甲氧基苯基)乙炔基]吡啶
  参考文献：
  名称：

  Sonogashira Coupling Reaction with Diminished Homocoupling

  摘要：

  The side product from homocoupling reaction of two terminal acetylenes in the Sonogashira reaction can be reduced to about 2% using an atmosphere of hydrogen gas diluted with nitrogen or argon. Terminal arylethynes, diarylethynes, and a few new arylpyridylethynes with donor substituents have been synthesized in very good yields. Comparative control experiments suggest that the homocoupling yield is determined by concentration of both catalyst and oxygen.

  DOI：

  10.1021/ol034320+

文献信息

• Heteroaromatic quinoline compounds
  申请人：Verhoest R. Patrick

  公开号：US20060154931A1

  公开（公告）日：2006-07-13

  The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

  该发明涉及异芳香化合物，其作为有效的磷酸二酯酶（PDE）抑制剂。具体而言，该发明涉及选择性抑制PDE10的这些化合物。该发明还涉及用于制备这些化合物的中间体；包含这些化合物的药物组合物；以及利用这些化合物治疗某些中枢神经系统（CNS）或其他疾病的方法。
• Bicyclic Pyridinylpyrazoles
  申请人：MATTES Amos

  公开号：US20110251178A1

  公开（公告）日：2011-10-13

  Bicyclic pyridinylpyrazoles of the formula (I) in which the symbols have the meanings given in the description and agrochemically active salts thereof and their use for controlling unwanted microorganisms in crop protection and the protection of materials and for reducing mycotoxins in plants and plant parts, and also processes for preparing compounds of the formula (I).

  公式(I)的双环吡啶基吡唑化合物，其中符号的含义如描述中所示，以及其在农作物保护中控制不受欢迎微生物和保护材料以及减少植物和植物部分中霉菌毒素的用途，以及制备公式(I)化合物的方法。
• Synthesis of crown-containing and related hetarylphenylacetylenes and acetylenyl dyes
  作者：A. I. Vedernikov、N. A. Lobova、L. G. Kuz’mina、N. A. Aleksandrova、S. K. Sazonov、J. A. K. Howard、S. P. Gromov

  DOI：10.1007/s11172-012-0021-x

  日期：2012.1

  New 15(18)-crown-5(6)-containing and model methoxy-substituted 1-hetaryl-2-phenylacetylenes of the 4-pyridine and 2-benzothiazole series were synthesized using the addition of bromine to the ethylene fragment of the corresponding styrylheterocycles followed by dehydrobromination under the action of potassium tert-butoxide. The quaternization of the pyridylphenylacetylenes afforded new acetylenyl dyes. The structures of five synthesized compounds were determined by X-ray diffraction analysis.

  在叔丁醇钾的作用下，将溴加到相应苯乙烯杂环的乙烯片段上，然后进行脱氢溴化，合成了 4-吡啶和 2-苯并噻唑系列的新的含 15(18)-冠-5(6)和模型甲氧基取代的 1-芳基-2-苯乙炔。将吡啶苯乙炔季铵化后可得到新的乙炔染料。通过 X 射线衍射分析确定了五种合成化合物的结构。
• 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。
• New Donor–Acceptor 2-Aryl-3-(4-pyridyl)-2,5-norbornadienes as Thermally Reversible Photochromic Systems
  作者：Arumugasamy Elangovan、Chieh-Ju Wang、Tong-Ing Ho

  DOI：10.1246/cl.2003.1180

  日期：2003.12

  New donor–acceptor 2,3-diarylnorbornadienes (1N–4N) showing high quantum yields for the blue light induced valence isomerization from the norbornadienes into quadricyclanes and the latters’ thermal reversion are studied in comparison with their protonated counterparts.

  新的供体-受体 2,3-二芳基降冰片二烯 (1N-4N) 显示出蓝光诱导的从降冰片二烯到四环烷的价异构化的高量子产率，并与质子化对应物进行了比较研究了后者的热逆转。