7-methyl-3,4-dihydro-1H-pyrano[3,4-b]quinolin-1-one

• 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: 7-methyl-3,4-dihydro-1H-pyrano[3,4-b]quinolin-1-one
• 英文别名: 7-Methyl-3,4-dihydro-1H-pyrano[3,4-b]quinolin-1-one；7-methyl-3,4-dihydropyrano[3,4-b]quinolin-1-one
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: ORIMMLBVFYHENV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-methyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline-4-carboxylic acid ethyl ester 在 硫酸 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以85%的产率得到7-methyl-3,4-dihydro-1H-pyrano[3,4-b]quinolin-1-one
  参考文献：
  名称：

  甘氨酸衍生物喹啉融合内酯和内酰胺的催化方法

  摘要：

  探索了一种双催化剂体系[氯化铜（II）硫酸，（CuCl 2 -H 2 SO 4）]-促进甘氨酸衍生物与2,3-二氢呋喃或2,3-二氢吡咯的好氧氧化反应，得到了有效合成高价值的喹啉融合内酯和内酰胺。以简洁的三步顺序完成了这种新方法在合成荧光素A的生物活性C环延伸类似物方面的应用。

  DOI：

  10.1002/adsc.201500513

文献信息

• Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions
  作者：Eva Schendera、Alexander Villinger、Malte Brasholz

  DOI：10.1039/d0ob01494j

  日期：——

  photoinduced aerobic tandem dehydrogenative Povarov cyclisation/Csp3–H oxygenation reactions between N-aryl glycine esters and α-substituted styrenes, which efficiently lead to 4,4-disubstituted dihydroquinoline-3-ones under mild conditions. The reactions are mediated by iodine along with visible light irradiation, which allows for the in situ generation of the essential Brønsted acid HI, to catalyse

  我们报告了N-芳基甘氨酸酯和 α-取代苯乙烯之间的无金属光诱导好氧串联脱氢 Povarov 环化/C sp 3 -H 氧化反应，在温和条件下有效地产生 4,4-二取代二氢喹啉-3-酮。该反应由碘和可见光照射介导，允许原位产生必需的布朗斯台德酸 HI，以催化关键的亚胺 [4+2]-环加成。
• Auto-Oxidative Coupling of Glycine Derivatives
  作者：Congde Huo、Yong Yuan、Mingxia Wu、Xiaodong Jia、Xicun Wang、Fengjuan Chen、Jing Tang

  DOI：10.1002/anie.201406905

  日期：2014.12.1

  The unprecedented title reaction between glycine derivatives and indoles, as well as the auto‐oxidative Povarov/aromatization tandem reaction of glycine derivatives with olefins are described. The reactions were performed in the absence of redox‐active catalysts and chemical oxidants under mild reaction conditions. Only simple organic solvents and air (or O2) were required.

  描述了甘氨酸衍生物和吲哚之间空前的标题反应，以及甘氨酸衍生物与烯烃的自氧化Povarov /芳香化串联反应。反应在温和的反应条件下，在没有氧化还原活性催化剂和化学氧化剂的情况下进行。仅需要简单的有机溶剂和空气（或O 2）。
• Construction of quinoline-fused lactones and 2,3-disubstituted quinolines via catalytic aerobic sp3 C–H oxidation: application of fragment-reassembly strategy
  作者：Xingge Ma、Yingzu Zhu、Shiwei Lü、Liang Zhang、Liangliang Luo、Xiaodong Jia

  DOI：10.1016/j.tetlet.2016.02.055

  日期：2016.4

  by fragment-reassembly strategy, the reaction between glycine esters and cyclic enol ethers was achieved in the catalysis of TBPA+·/O2, yielding a series of quinoline-fused lactones and 2,3-disubstituted quinolines. This approach provided an efficient method to construct quinoline skeleton, in which two new rings and two new C–C bonds were built in one pot.

  通过片段重组策略设计，在TBPA +· / O 2的催化作用中实现了甘氨酸酯与环状烯醇醚之间的反应，生成了一系列喹啉稠合的内酯和2,3-二取代喹啉。这种方法提供了一种构造喹啉骨架的有效方法，其中在一个罐中建立了两个新的环和两个新的C-C键。
• Metal-free photocatalyzed aerobic oxidative C_sp3–H functionalization of glycine derivatives: one-step generation of quinoline-fused lactones
  作者：Youxiang He、Baorun Yan、Hua Tao、Yuan Zhang、Ying Li

  DOI：10.1039/c8ob00240a

  日期：——

  This reaction provides facile access to a series of valuable quinoline-fused lactones at room temperature under an air atmosphere.

  这种反应在室温下，在空气氛围下提供了一系列有价值的喹啉融合内酯的便捷合成方法。
• Iron Catalyzed Dual-Oxidative Dehydrogenative (DOD) Tandem Annulation of Glycine Derivatives with Tetrahydrofurans
  作者：Congde Huo、Fengjuan Chen、Yong Yuan、Haisheng Xie、Yajun Wang

  DOI：10.1021/acs.orglett.5b02504

  日期：2015.10.16

  A novel iron-catalyzed dual-oxidative dehydrogenative (DOD) tandem annulation of glycine derivatives with tetrahydrofurans (THFs) for the synthesis of high value quinoline fused lactones has been developed. The reactions were performed under mild reaction conditions. And the use of cheap substrates (glycine derivatives and THF) and an even cheaper simple inorganic iron salt as the catalyst makes this protocol very attractive for potential synthetic applications.