N,6-dimethyl-4-phenylquinoline-2-carboxamide | 1451565-71-1

• 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: N,6-dimethyl-4-phenylquinoline-2-carboxamide
• CAS: 1451565-71-1
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: FGWFJURGQAEULD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙烯 、 N-methyl-2-[(4-methylphenyl)amino]acetamide 在 [Au(pyox^iPr)Cl₂][PF₆] 、 氧气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 以92%的产率得到N,6-dimethyl-4-phenylquinoline-2-carboxamide
  参考文献：
  名称：

  金-恶唑啉配合物催化甘氨酸衍生物与烯烃的交叉脱氢偶联

  摘要：

  利用甘氨酸衍生物和烯烃开发了金恶唑啉配合物催化的脱氢Povarov /氧化串联反应，用于合成修饰的喹啉。该反应在氧气作为氧化剂的存在下，在温和的反应条件下进行，并具有广泛的底物范围和出色的官能团耐受性。

  DOI：

  10.1002/adsc.201601066

文献信息

• Catalytic sp³ C–H Oxidation of Peptides and Their Analogues by Radical Cation Salts: From Glycine Amides to Quinolines
  作者：Xiaodong Jia、Yaxin Wang、Fangfang Peng、Congde Huo、Liangliang Yu、Jing Liu、Xicun Wang

  DOI：10.1021/jo401018v

  日期：2013.9.20

  A catalytic α-sp3 C–H oxidation of peptides and glycine amides was achieved under radical cation salt catalysis in the presence of O2, producing a series of substituted quinolines. The scope of this reaction shows good functional group tolerance and high efficiency of the oxidative functionalization.

  一种催化α-SP 3肽和甘氨酸酰胺的C-H的氧化是在的O-存在下自由基阳离子盐催化达到2，生产了一系列取代的喹啉的。该反应的范围显示出良好的官能团耐受性和氧化官能化的高效率。
• 一种4-苯基喹啉类化合物、其制备方法及应用
  申请人：贾忠

  公开号：CN106946776B

  公开（公告）日：2019-11-08

  本发明公开了一种4‑苯基喹啉类化合物、其制备方法及应用，本发明的4‑苯基喹啉类化合物去，其结构如下述式（Ⅰ）所示：其中，R1为–OH、–Cl、–O 或–CH3；R2为–H、– CO2 CH2 。本发明的4‑苯基喹啉类化合物可应用在抗结核杆菌药物的制备中。
• An economical synthesis of substituted quinoline-2-carboxylates through the potassium persulfate-mediated cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins
  作者：Guoliang Liu、Jiarui Qian、Jing Hua、Feng Cai、Xia Li、Lei Liu

  DOI：10.1039/c5ob02216a

  日期：——

  A practical and economical K2S2O8-mediated oxidative cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins has been established, affording structurally diverse quinoline-2-carboxylates in good to high efficiency. The low cost, negligible toxicity, and ease of handling of K2S2O8 combined with the absence of hazardous byproducts and the easy workup consisting of simple filtration are attractive based on economic and environmental factors.

  一种实用、经济的 K2S2O8 介导的 N-芳基甘氨酸衍生物与烯烃的氧化交叉脱氢偶联方法已经建立，可高效地获得结构多样的喹啉-2-羧酸盐。基于经济和环境因素，K2S2O8 具有成本低、毒性可忽略不计、易于处理、不产生有害副产物以及只需简单过滤等优点。
• Copper(II) Triflate-Catalyzed Aerobic Oxidative CH Functionalization of Glycine Derivatives with Olefins and Organoboranes
  作者：Zhiyu Xie、Jiong Jia、Xigong Liu、Lei Liu

  DOI：10.1002/adsc.201501015

  日期：2016.3.17

  triflate‐catalyzed aerobic oxidative CH functionalization of glycine derivatives with olefins and organoboranes has been established. The mild reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both glycine derivatives and the two types of nucleophilic components, allowing for the facile synthesis of diverse substituted quinolines and glycine derivatives bearing

  建立了经济实用的三氟甲磺酸铜（II）催化甘氨酸衍生物与烯烃和有机硼烷的好氧氧化CH功能化。温和的反应具有优异的官能团耐受性，并且在甘氨酸衍生物和两种类型的亲核组分方面均显示出广阔的范围，从而可以轻松合成各种取代的喹啉和甘氨酸衍生物，这些衍生物在α-中具有各种功能模式位置。
• CBr₄-Mediated Cross-Dehydrogenative Coupling Reaction of Amines
  作者：Congde Huo、Haisheng Xie、Mingxia Wu、Xiaodong Jia、Xicun Wang、Fengjuan Chen、Jing Tang

  DOI：10.1002/chem.201500453

  日期：2015.4.7

  AbstractA novel CBr4‐mediated dehydrogenative Povarov/aromatization tandem reaction of glycine derivatives with alkenes, leading to complex quinoline derivatives, and a CBr4‐mediated dehydrogenative CH functionalization of N‐aryl tetrahydroisoquinolines with nucleophiles to form CC and CP bonds are reported. The reactions were performed under very simple and mild reaction conditions; only CBr4 was used as a promoter. A plausible mechanism involving a radical process is proposed.