3-methoxycarbonyl-1-methyl-2(1H)-quinolone | 135585-55-6

• 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: 3-methoxycarbonyl-1-methyl-2(1H)-quinolone
• 英文别名: methyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate；methyl 1-methyl-2-oxoquinoline-3-carboxylate
• CAS: 135585-55-6
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: UNJIUZWKVJLTAF-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  329.2±41.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxycarbonyl-1-methyl-2(1H)-quinolone 在 sodium methylate 作用下， 以 邻二甲苯 为溶剂， 反应 82.0h， 生成 cis-6a-acetyl-5,6,6a,7,10,10a-hexahydro-5,8,9-trimethylphenanthridin-6-one
  参考文献：
  名称：

  Diels-Alder Cycloadditions of 2(1H)-Quinolones Having an Electron-Withdrawing Group at the 3-Position Acting as Dienophiles with Dienes.

  摘要：

  在大气压力及高压条件下，于3-位带有吸电子基团的2(1H)-喹诺酮与烷基-及硅氧基-1,3-丁二烯（2a, b）进行Diels-Alder环加成反应，可区域选择性或立体选择性地得到富功能化的菲啶酮。此外，利用分子轨道计算，对3-取代的2(1H)-喹诺酮与2a, b的区域选择性及化学选择性进行了研究。

  DOI：

  10.1248/cpb.49.893
• 作为产物：
  描述：

  2-氧-1,2-二氢喹啉-3-羧酸甲酯 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以0.276 g的产率得到3-methoxycarbonyl-1-methyl-2(1H)-quinolone
  参考文献：
  名称：

  Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis

  摘要：

  Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.

  DOI：

  10.1021/ol2019423

文献信息

• Direct Transformation of Baylis-Hillman Acetates into N-Substituted Quinolones through an SN2′ → SNAr → (Δ3,4-Δ2,3 Shift) → Oxidation Sequence
  作者：Muraleedharan Kannoth Manheri、John Napoleon

  DOI：10.1055/s-0030-1260189

  日期：2011.10

  SN2′-SNAr cyclization in the presence of alkyl or aralkyl amines, Baylis-Hillman acetates gave the corresponding 1,2-dihydroquinolines, which on simple exposure to light and oxygen afforded the corresponding 4- and 2-quinolones through sensitized oxidation or a Δ³,4-Δ²,³ shift → oxidation cascade. The mechanism of the oxidation step, the stabilities of the 1,2- and 1,4-dihydroquinolines in solution and

  当在烷基或芳烷基胺存在下进行串联S N 2'-S N Ar环化反应时，Baylis-Hillman乙酸酯可得到相应的1,2-二氢喹啉，将其简单地暴露于光和氧气下可得到相应的4-和2喹诺酮类化合物通过敏化氧化或Δ³，4-- Δ² ，³转变→氧化级联反应。讨论了氧化步骤的机理，溶液中和固态的1,2-和1,4-二氢喹啉的稳定性以及关键中间体向已知治疗剂的合成工艺。 抗生素-环化-喹啉-自由基反应-光氧化
• Cycloadditions of 1-Substituted 1,3-Butadienes with 4- or 3-Substituted 2(1H)-Quinolones Acting as Dienophiles.
  作者：Reiko Fujita、Kanako Oikawa、Toshiteru Yoshisuji、Yuko Okuyama、Hiroto Nakano、Hisao Matsuzaki

  DOI：10.1248/cpb.51.295

  日期：——

  Cycloadditions of 1,3-butadiene derivatives having an electron-rich group at the 1-position with 4- or 3-substituted 2(1H)-quinolones were carried out to give the richly functionalized phenanthridines under both atmospheric and high pressure conditions. Furthermore, the reactivity of 4- or 3-substituted 2(1H)-quinolones acting as a dienophile with 1-substituted dienes was examined using MO calculation.

  在常压和高压条件下，将1位具有富电子基团的1,3-丁二烯衍生物与4-或3-取代的2(1H)-喹诺酮进行环加成，得到富官能化的菲啶。此外，使用MO计算检查了作为亲二烯体的4-或3-取代的2(1H)-喹诺酮与1-取代二烯的反应性。
• Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis
  作者：Benjamin L. Kohn、Elizabeth R. Jarvo

  DOI：10.1021/ol2019423

  日期：2011.9.16

  Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.
• Diels-Alder Cycloadditions of 2(1H)-Quinolones Having an Electron-Withdrawing Group at the 3-Position Acting as Dienophiles with Dienes.
  作者：Reiko FUJITA、Kazuhiro WATANABE、Toshiteru YOSHISUJI、Chizuko KABUTO、Hisao MATSUZAKI、Hiroshi HONGO

  DOI：10.1248/cpb.49.893

  日期：——

  Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1, 3-butadienes (2a, b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examined using MO calculation.

  在大气压力及高压条件下，于3-位带有吸电子基团的2(1H)-喹诺酮与烷基-及硅氧基-1,3-丁二烯（2a, b）进行Diels-Alder环加成反应，可区域选择性或立体选择性地得到富功能化的菲啶酮。此外，利用分子轨道计算，对3-取代的2(1H)-喹诺酮与2a, b的区域选择性及化学选择性进行了研究。