(E)-2-(3-methoxystyryl)quinoline | 1289213-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-2-(3-methoxystyryl)quinoline
• 英文别名: 2-[(E)-2-(3-methoxyphenyl)ethenyl]quinoline
• CAS: 1289213-22-4
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: OWVUAWQYNRCLFF-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-2-(3-methoxystyryl)quinoline 在 氧气 、 高氯酸 作用下， 以 乙腈 为溶剂， 以52%的产率得到3-methoxyquinolino[1,2-a]quinolinium perchlorate
  参考文献：
  名称：

  Regiospecific C–N Photocyclization of 2-Styrylquinolines

  摘要：

  Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4)2.

  DOI：

  10.1021/jo500696n
• 作为产物：
  描述：

  C₁₈H₁₅NO 以 乙腈 为溶剂， 生成 (E)-2-(3-methoxystyryl)quinoline
  参考文献：
  名称：

  Regiospecific C–N Photocyclization of 2-Styrylquinolines

  摘要：

  Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4)2.

  DOI：

  10.1021/jo500696n

文献信息

• Nickel-Catalyzed Direct Alkenylation of Methyl Heteroarenes with Primary Alcohols
  作者：Bose Muthu Ramalingam、Isai Ramakrishna、Mahiuddin Baidya

  DOI：10.1021/acs.joc.9b01517

  日期：2019.8.2

  An efficient nickel-catalyzed acceptorless dehydrogenative coupling of methyl-substituted heteroarenes with primary alcohols is achieved using an in situ generated complex of inexpensive NiBr2 and readily available 8-aminoquinoline picolinic amide ligand. The protocol is operationally simple and scalable and furnishes a series of high-value 2-alkenylheteroarenes in good yields (up to 88%) with exclusive

  甲基取代的杂芳烃与伯醇的有效的镍催化的无受体脱氢偶联是通过使用廉价的NiBr 2和容易获得的8-氨基喹啉吡啶甲酸酰胺配体的原位生成的络合物实现的。该协议操作简单，可扩展，并提供了一系列具有高收率（高达88％）的高价值2-烯基杂芳烃，并且具有独特的E选择性。反应进行时会释放出水和氢分子，然后通过气相色谱进行分析以验证反应机理。
• Oxidative Olefination of Secondary Amines­ with Carbon Nucleophiles
  作者：Yong-Gang Zhang、Jing-Kun Xu、Xi-Ming Li、Shi-Kai Tian

  DOI：10.1002/ejoc.201300368

  日期：2013.6

  An unprecedented olefination reaction of secondary amines with carbon nucleophiles has been developed through C–N/C–H functionalization under metal-free oxidative conditions. In the presence of a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a range of secondary N-alkylanilines smoothly underwent oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile

  在无金属氧化条件下，通过 C-N/C-H 官能化开发了一种前所未有的仲胺与碳亲核试剂的烯化反应。在化学计量的 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 存在下，一系列仲 N-烷基苯胺与 2-烷基氮杂芳烃、苯乙酮和丙二腈顺利地进行氧化烯化，得到以中等至优异的产率和优异的 (E) 选择性提供结构多样的多取代烯烃。初步机理研究表明，氧化烯化反应通过胺氧化和亚胺烯化进行。
• NaCl as Catalyst and Water as Solvent: Highly <i>E</i>-Selective Olefination of Methyl Substituted <i>N</i>-Heteroarenes with Benzyl Amines and Alcohols
  作者：Susanta Hazra、Vikas Tiwari、Ashutosh Verma、Pritam Dolui、Anil J. Elias

  DOI：10.1021/acs.orglett.0c01851

  日期：2020.7.17

  Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that

  苄基胺和醇与甲基取代的N-杂芳烃如喹啉和喹喔啉的氧化偶联已使用氯化物实现，氯化物是一种富含海的阴离子，可作为催化剂在水性介质中实际合成各种E-二取代的烯烃。详述机理研究和控制实验进行推断，其表明反应机理原位形成CLO 2 -是该催化剂的活性形式。我们已经成功地使用这种方法进行了1 g规模的反应，并且通过这种方法还以中等至良好的产率合成了5种药学上相关的共轭烯烃。
• Ru(II)–NNO pincer‐type complexes catalysed E‐olefination of alkyl‐substituted quinolines/pyrazines utilizing primary alcohols
  作者：Veerappan Tamilthendral、Gunasekaran Balamurugan、Rengan Ramesh、Jan Grzegorz Malecki

  DOI：10.1002/aoc.6561

  日期：2022.3

  strategy is operationally simple and scalable and tolerates various functional groups under mild reaction conditions. Notably, an aldehyde and aryl-2-quinoline-2-yl-ethanol intermediate are involved in the catalytic reaction mechanism. The utility of the present procedure is demonstrated through a facile synthesis of the antifungal drug (E)-2-(2-(pyridin-4-yl)vinyl)quinoline.

  证明了通过由包含羰基和三苯胂作为共配体的 Ru(II)–N^N^O 钳型络合物催化的醇的无受体脱氢偶联，烷基取代的喹啉和吡嗪的有效和选择性 E-烯烃化。通过分析和光谱方法合成和评估了一系列 Ru(II) 催化剂。合成配合物的固态分子结构 ( 2) 已通过 X 射线晶体学证实。该催化协议通过使用现成的伯醇生产出高达 90% 的各种烯烃产品。目前的合成策略操作简单且可扩展，并且在温和的反应条件下耐受各种官能团。值得注意的是，醛和芳基-2-喹啉-2-基-乙醇中间体参与了催化反应机理。本程序的实用性通过抗真菌药物 (E)-2-(2-(pyridin-4-yl)vinyl)quinoline 的简便合成得到证明。
• Iron/TEMPO-catalyzed direct aerobic oxidative coupling of methyl-mubstituted N-heteroazaarenes with alcohols
  作者：Zhiguang Zhang、Yantao Ma、Siwei Dai、Ling Li、Yong Zhang、Hao Li

  DOI：10.1016/j.tetlet.2020.151885

  日期：2020.5

  A novel direct oxidative coupling of methyl-substituted N-heteroazaarenes with alcohols has been developed to construct olefins under mild condition. The reaction is catalyzed by Fe(NO3)3·9H2O/TEMPO with oxygen as terminal oxidant. A variety of E-disubstituted olefins bearing diverse functional groups could be obtained selectively in moderate to excellent yields. The reaction is environmentally friendly

  已经开发了甲基取代的N-杂氮杂芳烃与醇的新颖的直接氧化偶联，以在温和的条件下构建烯烃。Fe（NO 3）3 ·9H 2 O / TEMPO以氧为末端氧化剂催化反应。可以以中等至优异的产率选择性地获得各种带有不同官能团的E-二取代的烯烃。该反应对环境友好且不含配体。