(E)-2-(3-nitrostyryl)quinoline | 38101-92-7

• 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-nitrostyryl)quinoline
• 英文别名: 3-[2-(quinolin-2-yl)ethenyl]nitrobenzene；2-[(E)-2-(3-nitrophenyl)vinyl]quinoline；2-[(E)-2-(3-nitrophenyl)ethenyl]quinoline
• CAS: 38101-92-7
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: URIXDBULDXTIHZ-CSKARUKUSA-N

物化性质

• 沸点：
  455.4±24.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(3-nitrostyryl)quinoline 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 反应 1.0h， 生成 E-3-[2-(quinolin-2-yl)ethenyl]aniline
  参考文献：
  名称：

  发现OT4003，这是一种新型的，有效的，口服活性的cys-LT1受体拮抗剂。

  摘要：

  本文介绍了结构修饰，导致发现了一系列新的含喹啉的cys-LT1受体（LTD4受体）拮抗剂。为了获得目标化合物OT4003，进行了关于体外受体结合，体内支气管收缩和过氧化物酶体增殖形式的毒理学效应的结构优化。发现OT4003（（S）-（+）-E-2-（3-（2-（7-氯喹啉-2-基）乙烯基）苯基氨基甲基）-苯氧基++ +己酸）是一种有效的选择性抑制剂[3H] LTD4与豚鼠肺膜特异性结合（IC50 2.4 +/- 1.0 nM），也是强效，口服活性的LTD4诱导豚鼠支气管收缩的拮抗剂[ED50 0.14（ED16 0.1-ED84 0.4）mg / kg ; 预处理4小时]。

  DOI：

  10.1016/s0968-0896(96)00253-2
• 作为产物：
  描述：

  2-[(Z)-2-(3-nitrophenyl)ethenyl]quinoline 以 乙腈 为溶剂， 生成 (E)-2-(3-nitrostyryl)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

• Iodine-Catalyzed Direct C–H Alkenylation of Azaheterocycle N-Oxides with Alkenes
  作者：Zhenhao Zhang、Chao Pi、Heng Tong、Xiuling Cui、Yangjie Wu

  DOI：10.1021/acs.orglett.6b03399

  日期：2017.2.3

  azaheterocycle N-oxides with alkenes catalyzed by iodine under metal- and external oxidant-free reaction conditions has been developed. A variety of (E)-2-styrylazaheterocycles have been produced in moderate to excellent yields. The mechanistic exploration indicated that the N-oxide group played dual roles as both the directing group and an internal oxidant in this catalytic cycle.

  在无金属和无外部氧化剂的反应条件下，开发了一种有效的且区域选择性的氮杂杂环N-氧化物与碘催化的烯烃的区域选择性烯基化方法。已经以中等至优异的产率生产了多种（E）-2-苯乙烯基杂氮杂杂环。机理探索表明，在该催化循环中，N-氧化物基团既充当导向基团又充当内部氧化剂。
• Lewis-Acid-Catalyzed Benzylic Reactions of 2-Methylazaarenes with Aldehydes
  作者：Dan Mao、Gang Hong、Shengying Wu、Xin Liu、Jianjun Yu、Limin Wang

  DOI：10.1002/ejoc.201400073

  日期：2014.5

  Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes have been investigated. Series of azaarene derivatives were afforded by this reaction. 2-(Pyridin-2-yl)ethanols with common substituents were formed through the LiNTf2-promoted aldol reaction for the first time. 2-Alkenylpyridines, exclusively in the form of the E isomers, were synthesized in the presence of LiNTf2 cooperated

  已经研究了路易斯酸催化的 2-甲基氮杂芳烃与醛的苄基反应。该反应得到一系列氮杂芳烃衍生物。首次通过LiNTf2促进的羟醛反应形成了具有常见取代基的2-(Pyridin-2-yl)乙醇。在 LiNTf2 与 H2NTf 协同作用下，合成了仅以 E 异构体形式存在的 2-烯基吡啶。在La(Pfb)3催化下，2-甲基喹啉与醛类在空气中反应，以高收率得到2-烯基喹啉。
• Iron-catalyzed C(sp³)–H functionalization of methyl azaarenes: a green approach to azaarene-substituted α- or β-hydroxy carboxylic derivatives and 2-alkenylazaarenes
  作者：Danwei Pi、Kun Jiang、Haifeng Zhou、Yuebo Sui、Yasuhiro Uozumi、Kun Zou

  DOI：10.1039/c4ra10939b

  日期：——

  An iron-catalyzed C(sp³)–H functionalization of methyl azaarenes with carbonyls to access the title compounds have been described.

  使用铁催化的C(sp³)-H官能团化方法，将甲基氮杂芳烃与羰基化合物反应，合成了目标化合物。

• Aminostyryl compound, leukotriene antagonistic composition containing
  申请人：Mitsubishi Chemical Industries Limited

  公开号：US04749701A1

  公开（公告）日：1988-06-07

  Disclosed are an aminostyryl compound represented by Formula I: ##STR1## wherein A represents a linking group having 3 to 4 chain members; B represents an unsubstituted or substituted 5 to 6-membered monocyclic type heterocyclic residue containing 1 to 2 hetero atoms, an unsubstituted or substituted condensed heterocyclic residue which contains 5 to 6-membered monocyclic type heterocycle containing 1 to 2 hetero atoms, a naphthyl group or an alkyl group having 5 to 7 carbon atoms, a composition having leukotriene antagonism which contains an aminostyryl compound represented by Formula I as the effective ingredient, and a method of antagonizing SRS based on leukotriene antagonistic activity by employing the same.

  公开了一种由式I表示的氨基芳基化合物：##STR1##其中A代表具有3到4个链成员的连接基团；B代表未取代或取代的含有1到2个杂原子的5到6元单环型杂环残基，未取代或取代的含有5到6个单环型杂环的缩合杂环残基，一个萘基或具有5到7个碳原子的烷基基团，一种含有氨基芳基化合物作为有效成分的具有白三烯拮抗作用的组合物，以及利用该组合物对基于白三烯拮抗活性的SRS进行拮抗的方法。
• Facile synthesis of 2-alkenylazaarenes via dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’
  作者：Shiheng Fu、Liang Wang、Haoxun Dong、Junqiang Yu、Lubin Xu、Jian Xiao

  DOI：10.1016/j.tetlet.2016.08.065

  日期：2016.10

  A catalyst-free dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’ has been developed for efficient synthesis of (E)-2-alkenylazaarenes. The challenging addition/dehydration of aliphatic aldehyde was successfully implemented using water as a solvent. A variety of 2-methylazaarenes, aromatic and aliphatic aldehydes were well tolerated.

  已经开发了2-甲基氮杂芳烃与醛“在水上”的无催化剂的脱水偶联，以有效地合成（E）-2-链烯基氮杂芳烃。使用水作为溶剂成功地实现了具有挑战性的脂族醛的添加/脱水。各种2-甲基氮杂芳烃，芳族和脂族醛均具有良好的耐受性。