(Z)-2-styrylquinoline | 80998-91-0

• 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: (Z)-2-styrylquinoline
• 英文别名: 2-Styryl-chinolin；2-Styrylchinolin；cis-2-Styrylquinoline；2-[(Z)-2-phenylethenyl]quinoline
• CAS: 80998-91-0
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: RLGKSXCGHMXELQ-BENRWUELSA-N

物化性质

• 沸点：
  387.0±17.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-styrylquinoline 以 乙腈 为溶剂， 生成 2-苯乙烯基喹啉
  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：

  2-(2-苯基乙炔基)喹啉 在 喹啉 、 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 以65%的产率得到(Z)-2-styrylquinoline
  参考文献：
  名称：

  Studies on quinoline and isoquinoline derivatives. VIII. Hydration and hydrogenation of ethynyl substituents attached to the pyridine moiety of quinoline and isoquinoline rings.

  摘要：

  研究针对含有乙炔取代基与吡啶结构直接相连的喹啉和异喹啉衍生物的三重键的水合和氢化进行了研究。十四种乙炔喹啉和异喹啉，例如2-、3-、4-苯乙炔喹啉，2-、3-、4-(1-己炔)喹啉，2-(1-丙炔)喹啉，1-、3-、4-苯乙炔异喹啉，1-、3-、4-(1-己炔)异喹啉，和1-(1-丙炔)异喹啉，在稀硫酸中与硫酸汞共热时，高选择性地转化为相应的酰基甲基衍生物。在所有情况下，没有分离出由于反向水合产生的产物。上述化合物的乙炔键的部分催化还原是可行的，而彻底还原则生成侧链饱和的喹啉和异喹啉。

  DOI：

  10.1248/cpb.29.3554

文献信息

• A sustainable metal-free and additive-free olefination route to <i>N</i>-heteroazaarenes from methyl-substituted heterocycles and amines
  作者：Hongyi Cui、Chunyan Zhang、Yuqi Ji、Guoying Zhang

  DOI：10.1039/d4ra00189c

  日期：——

  A green and sustainable metal-free, additive-free olefination approach is proposed for the facile synthesis of various unsaturated N-heteroazaarenes from simple methyl-substituted heteroarenes and amines. The developed protocol employs only air as the sole oxidant and provides a useful strategy for obtaining various E-selective conjugated heterocyclic olefins. This provides a useful strategy for application

  提出了一种绿色且可持续的无金属、无添加剂的烯烃化方法，用于从简单的甲基取代杂芳烃和胺中轻松合成各种不饱和 N-杂芳烃。开发的方案仅使用空气作为唯一的氧化剂，并为获得各种 E 选择性共轭杂环烯烃提供了一种有用的策略。这为在一个罐中生成克数的各种不饱和 N-杂杂芳烃（高达 20.33 克）和具有高区域选择性的 STB-8（2.40 克）合成显像剂提供了一种有用的策略。
• A Catalyst-Free Benzylic C–H Bond Olefination of Azaarenes for Direct Mannich-like Reactions
  作者：Yizhe Yan、Kun Xu、Yang Fang、Zhiyong Wang

  DOI：10.1021/jo2008934

  日期：2011.8.19

  A highly efficient synthesis of trans-alkenylazaarene under catalyst-free conditions was developed via the addition of methylazaarenes to N-sulfonyl aldimines and a subsequent C-N elimination in situ. A one-pot procedure for this addition-elimination was also developed. The reaction could tolerate a broad substrate scope and give the corresponding alkenylazaarenes in high yields.
• Brønsted acid catalyzed synthesis of 1,3-di(2-quinolyl)propane derivatives via tandem C(sp3)–H functionalization
  作者：Jia-jia Jin、Dong-chao Wang、Hong-ying Niu、Shan Wu、Gui-rong Qu、Zhong-bo Zhang、Hai-ming Guo

  DOI：10.1016/j.tet.2013.05.135

  日期：2013.8

  A novel protocol for Bronsted acid catalyzed reaction of 2-methyl azaarenes and aromatic aldehyde to give 1,3-di(2-quinolyl)propane derivatives through tandem C(sp(3))-H bond functionalization has been developed. This approach provides a new access to a variety of 1,3-di(2-quinolyl)propane derivatives, which are potentially of great importance in pharmaceuticals and ligand fields. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel approach to synthesis of 1′,4′-dihydro-2,3′-biquinolines
  作者：V. V. Trifonov、I. V. Aksenova、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-006-0036-z

  日期：2005.12
• Studies on quinoline and isoquinoline derivatives. VIII. Hydration and hydrogenation of ethynyl substituents attached to the pyridine moiety of quinoline and isoquinoline rings.
  作者：SHOETSU KONNO、MASAFUMI SHIRAIWA、HIROSHI YAMANAKA

  DOI：10.1248/cpb.29.3554

  日期：——

  Studies were carried out on the hydration and hydrogenation of the triple bond in quinoline and isoquinoline derivatives containing an ethynyl substituent linked directly to the pyridine moiety. Fourteen kinds of ethynyl quinolines and isoquinolines such as 2-, 3-, 4-phenylethynylquinoline, 2-, 3-, 4-(1-hexynyl) quinoline, 2-(1-propynyl) quinoline, 1-, 3-, 4-phenylethynylisoquinoline, 1-, 3-, 4-(1-hexynyl) isoquinoline, and 1-(1-propynyl)-isoquinoline were converted into the corresponding acylmethyl derivatives with high selectivity, when they were heated in dilute sulfuric acid in the presence of mercuric sulfate. In all cases, no products due to reverse hydration were isolated. Partial catalytic reduction of the ethynyl linkage of the above compounds is possible, while exhaustive reduction afforded quinolines and isoquinolines with a saturated side chain.

  研究针对含有乙炔取代基与吡啶结构直接相连的喹啉和异喹啉衍生物的三重键的水合和氢化进行了研究。十四种乙炔喹啉和异喹啉，例如2-、3-、4-苯乙炔喹啉，2-、3-、4-(1-己炔)喹啉，2-(1-丙炔)喹啉，1-、3-、4-苯乙炔异喹啉，1-、3-、4-(1-己炔)异喹啉，和1-(1-丙炔)异喹啉，在稀硫酸中与硫酸汞共热时，高选择性地转化为相应的酰基甲基衍生物。在所有情况下，没有分离出由于反向水合产生的产物。上述化合物的乙炔键的部分催化还原是可行的，而彻底还原则生成侧链饱和的喹啉和异喹啉。