8-methyl-3-phenyl-1H-pyrano[4,3-b]quinolin-1-one | 1421925-45-2

• 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: 8-methyl-3-phenyl-1H-pyrano[4,3-b]quinolin-1-one
• 英文别名: 8-Methyl-3-phenyl-pyrano[4,3-b]quinolin-1-one；8-methyl-3-phenylpyrano[4,3-b]quinolin-1-one
• CAS: 1421925-45-2
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: BCMLABFCOBQIOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methyl-3-phenyl-1H-pyrano[4,3-b]quinolin-1-one 在 ammonium hydroxide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-chloro-8-methyl-3-phenylbenzo[b][1,6]naphthyridine
  参考文献：
  名称：

  An economical nucleophilic route toward facile synthesis of pyrano[4,3-b]quinolin-1-ones via 6-endo-dig cyclization of o-alkynylquinoline esters

  摘要：

  Metal-free facile synthesis of pyrano[4,3-b]quinoline-1-ones is described from methyl 2-arylethynyl-quinoline-3-carboxylates via intramolecular cyclization in excellent yields. The cyclization reactions are facilitated using cheap and easily available KOH base in MeOH. The reaction conditions did not require dry solvent, inert atmosphere, and avoid further column chromatography purification of the products. These compounds could be further used as building blocks for the synthesis of 2H-benzo[b][1,6]naphthyridin-1-one and 1-chloro-benzo[b][1,6]naphthyridines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.068
• 作为产物：
  描述：

  methyl 6-methyl-2-(phenylethynyl)quinoline-3-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以92%的产率得到8-methyl-3-phenyl-1H-pyrano[4,3-b]quinolin-1-one
  参考文献：
  名称：

  An economical nucleophilic route toward facile synthesis of pyrano[4,3-b]quinolin-1-ones via 6-endo-dig cyclization of o-alkynylquinoline esters

  摘要：

  Metal-free facile synthesis of pyrano[4,3-b]quinoline-1-ones is described from methyl 2-arylethynyl-quinoline-3-carboxylates via intramolecular cyclization in excellent yields. The cyclization reactions are facilitated using cheap and easily available KOH base in MeOH. The reaction conditions did not require dry solvent, inert atmosphere, and avoid further column chromatography purification of the products. These compounds could be further used as building blocks for the synthesis of 2H-benzo[b][1,6]naphthyridin-1-one and 1-chloro-benzo[b][1,6]naphthyridines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.068

文献信息

• Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives
  作者：Farzaneh Ansari、Hormoz Khosravi、Alireza Abbasi Kejani、Mahsa Armaghan、Walter Frank、Saeed Balalaie、Farnaz Jafarpour

  DOI：10.1039/d1ob00726b

  日期：——

  α-pyrone derivatives via the formation of two C–O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C–H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.

  开发了一种新颖且有效的烯醛无金属 C-H 官能化方法，通过形成两个 C-O 键来合成α-吡喃酮衍生物。在该项目中，K 2 S 2 O 8被引入作为区域选择性氧化环化反应中的有效氧源和C-H官能化剂，具有相对广泛的底物范围。
• TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones
  作者：Jay Bahadur Singh、Kalpana Mishra、Tanu Gupta、Radhey M. Singh

  DOI：10.1016/j.tetlet.2018.01.083

  日期：2018.3

  TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-dig cyclization. The probable mechanism is discussed.

  由邻炔基喹啉醛描述了TBHP促进的吡喃并[4,3 - b ]喹啉-1-酮的多米诺合成。自由基反应是在没有金属和添加剂的情况下进行的，方法是将醛键的CH键氧化为C-OH键，然后进行分子内6-内切环化。讨论了可能的机制。