2-methoxy-6-(phenylethynyl)naphthalene | 957768-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-6-(phenylethynyl)naphthalene
• 英文别名: 2-Methoxy-6-(2-phenylethynyl)naphthalene；2-methoxy-6-(2-phenylethynyl)naphthalene
• CAS: 957768-41-1
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: LOYLAMNTFNWDHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-(phenylethynyl)naphthalene 在 potassium permanganate 、 ammonium acetate 、 氧气 作用下， 以 丙酮 、 正丁醇 为溶剂， 反应 8.0h， 生成 2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-5-phenyl-1H-imidazole
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氧气 作用下， 以 二乙胺 、 乙腈 为溶剂， 反应 0.5h， 生成 2-methoxy-6-(phenylethynyl)naphthalene
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h

文献信息

• Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
  作者：Gabriel Charles Edwin Raja、Francis Mariaraj Irudayanathan、Han-Sung Kim、Jimin Kim、Sunwoo Lee

  DOI：10.1021/acs.joc.6b00883

  日期：2016.6.17

  the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes

  开发了一种Ni催化体系，用于炔基羧酸与有机硅烷的脱羧偶联反应。Ni（acac）2和1,10-菲咯啉在120°C下存在CsF和CuF 2时显示出最佳结果。该体系容许存在烷基，烷氧基，卤素，硝基，氰基，酮和酯官能团。此外，与丁-2-炔二酸和有机硅烷的反应提供了相应的对称二芳基炔烃。
• Oxidation of alkynes using PdCl2/CuCl2 in PEG as a recyclable catalytic system: one-pot synthesis of quinoxalines
  作者：S. Chandrasekhar、N. Kesava Reddy、V. Praveen Kumar

  DOI：10.1016/j.tetlet.2010.05.006

  日期：2010.7

  Alkynes were oxidized efficiently using the catalytic amount of PdCl2 and CuCl2 in PEG-400 in the presence of water, providing excellent yields of the corresponding 1,2-diketones. A variety of alkynes were well-suited substrates for the oxidation under the described conditions. Further, the optimized conditions were successfully utilized for the one-pot synthesis of 2,3-disubstituted quinoxaline derivatives

  在水存在下，使用PEG-400中的催化量的PdCl 2和CuCl 2催化有效地氧化炔烃，从而提供了极佳的相应1,2-二酮收率。多种炔烃是在所述条件下用于氧化的非常合适的底物。此外，优化的条件已成功用于一锅合成2，3-二取代的喹喔啉衍生物。
• Iron Pincer Complex Catalyzed, Environmentally Benign,<i>E</i>-Selective Semi-Hydrogenation of Alkynes
  作者：Dipankar Srimani、Yael Diskin-Posner、Yehoshoa Ben-David、David Milstein

  DOI：10.1002/anie.201306629

  日期：2013.12.23

  Ironing out hydrogenation: For the first time, an iron catalyst provided chemo‐ and stereo‐selective semi‐hydrogenation of alkynes to E‐alkenes. This efficient, atom‐economical reaction is catalyzed by a novel acridine‐based PNP iron pincer catalyst and exhibits excellent functional group tolerance under mild, neutral, environmentally benign reaction conditions.

  消除氢化：第一次，铁催化剂提供了炔烃化学和立体选择性半加氢成E烯烃的能力。这种新型的a啶基PNP铁钳催化剂可有效地进行这种原子经济的反应，在温和，中性，环境友好的反应条件下表现出优异的官能团耐受性。
• Copper-Catalyzed 2:1 Coupling Reaction of Arynes with Alkynes
  作者：Hiroto Yoshida、Takami Morishita、Hiromi Nakata、Joji Ohshita

  DOI：10.1021/ol802609j

  日期：2009.1.15

  A formal insertion reaction of two molar amounts of arynes into a C−H bond of terminal alkynes is efficaciously catalyzed by copper(I) chloride, giving 2-alkynylbiaryls in one step.

  氯化铜（I）有效地催化了两个摩尔量的芳烃在末端炔烃的CH键中的正式插入反应，一步即可得到2-炔基联芳基。
• Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive- and Amine-Free Reaction Conditions
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/adsc.200900112

  日期：2009.4

  Abstractmagnified imageSequential addition of 1,1′,1′′‐phosphinetriyltripiperidine and 1,3‐diaminobenzene or resorcinol to toluene solutions of (cyclooctadiene)palladium dichloride [Pd(cod)(Cl)2] under nitrogen in “one pot” almost quantitatively yielded the aminophosphine‐based pincer complexes [C6H3‐2,6‐(XPpiperidinyl}2)2]Pd(Cl)} (X=NH 1; X=O 2). Complex 1 (and to a minor extent 2) proved to be efficient Sonogashira catalysts, which allow the quantitative coupling of various electronically deactivated and/or sterically hindered and functionalized aryl iodides and aryl bromides with several alkynes as coupling partners within very short reaction times and low catalyst loadings. Importantly, in contrast to most of the Sonogashira catalysts, which either are both air‐ and moisture‐sensitive and/or require the addition of co‐catalysts, such as copper(I) iodide [CuI], for example, or a large excess of an amine, the coupling reactions were carried out without the use of amines, co‐catalysts or other aditives and without exclusion of air and moisture. Moreover, the desired products were exclusively formed (no side‐products were detected) without employing an excess of one of the substrates. Ethylene glycol and potassium phosphate (K3PO4) were found to be the ideal solvent and base for this transformation. Experimental observations strongly indicate that palladium nanoparticles are not the catalytically active form of 1 and 2. On the other hand, their transformation into another homogeneous catalytically active species cannot be excluded.