5,6,8-trimethoxy-4-methylquinolin-2(1H)-one | 152531-90-3

• 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: 5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
• 英文别名: 5,6,8-trimethoxy-4-methyl-1H-quinolin-2-one
• CAS: 152531-90-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: YRUICGVVPDTGCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6,8-trimethoxy-4-methylquinolin-2(1H)-one 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis of 2(1H)-Quinolinonequinones and 2-Alkoxyquinolinequinones Using Oxidative Demethylation with Cerium (IV) Ammonium Nitrate

  摘要：

  2,5,8(1H)-Quinolinetriones (12), 2,5,6(1H)-quinolinetriones (13), 2-alkoxy-5,8-quinolinediones (14), 2,8-dimethoxy-5,6-quinolinedione (15), and 2,6-dimethoxy-7,8-quinolinediones (16) were synthesized by oxidative demethylation of the corresponding 2(1H)-quinolinones (7) and 2-alkoxyquinolines (11) with cerium (IV) ammonium nitrate.

  DOI：

  10.3987/com-93-6404
• 作为产物：
  描述：

  2,4,5-三甲氧基苯胺 在 吡啶 、 PPA 作用下， 以 甲苯 为溶剂， 反应 3.17h， 生成 5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 2(1H)-Quinolinonequinones and 2-Alkoxyquinolinequinones Using Oxidative Demethylation with Cerium (IV) Ammonium Nitrate

  摘要：

  2,5,8(1H)-Quinolinetriones (12), 2,5,6(1H)-quinolinetriones (13), 2-alkoxy-5,8-quinolinediones (14), 2,8-dimethoxy-5,6-quinolinedione (15), and 2,6-dimethoxy-7,8-quinolinediones (16) were synthesized by oxidative demethylation of the corresponding 2(1H)-quinolinones (7) and 2-alkoxyquinolines (11) with cerium (IV) ammonium nitrate.

  DOI：

  10.3987/com-93-6404

文献信息

• Synthesis of 5,8- and 5,6-Quinolinediones Using Oxidative Demethylation with Cerium(IV) Ammonium Nitrate.
  作者：Yoshiyasu KITAHARA、Masanori NAGATSU、Yoshikazu SHIBANO、Akinori KUBO

  DOI：10.1248/cpb.45.1697

  日期：——

  4-Phenyl-5, 8-quinolinediones (7, 8, 12, 13), 4-phenyl-5, 6-quinolinediones (9, 14), and 2-dialkylamino-4-phenyl-5, 8-quinolinediones (17, 18), were synthesized by oxidative demethylation of the corresponding 5, 8-dimethoxy- or 5, 6, 8-trimethoxy-4-phenylquinolines with cerium(IV) ammonium nitrate. Sulfur-containing quinolinequinones (21, 24) were prepared by oxidation of the corresponding 5, 8-dimethoxy- or 5, 6, 8-trimethoxy-2(1H)-quinolinethiones (20, 23).

  4-苯基-5, 8-喹啉二酮（7, 8, 12, 13）、4-苯基-5, 6-喹啉二酮（9, 14）和2-二烷基氨基-4-苯基-5, 8-喹啉二酮（17, 18）通过将相应的5, 8-二甲氧基或5, 6, 8-三甲氧基-4-苯基喹啉与硝酸铈（IV）发生氧化去甲基化反应合成。含硫的喹啉喹醌（21, 24）则通过氧化相应的5, 8-二甲氧基或5, 6, 8-三甲氧基-2(1H)-喹啉硫酮（20, 23）制备而成。
• Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities
  作者：Arup Maiti、P. V. Narasimha Reddy、Megan Sturdy、Laura Marler、Scott D. Pegan、Andrew D. Mesecar、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm801335z

  日期：2009.4.9

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
• Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.steroids.2010.06.004

  日期：2010.12

  Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [C-11]casimiroin (6-[C-11]rnethoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [C-11]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ([C-11]17), 8-methoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ((11)[C]21a), 6,8-dimethoxy-1-(11)[C]methyl-4-methylquinolin-2(1H)-one ([C-11]21b), and 5,8-dimethoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ([C-11]21c), were prepared from their corresponding precursors with [C-11]methyl triflate ([C-11]CH3OTf) under basic conditions (NaH) through either O- or N-[C-11]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [C-11]CO2, and 111-185 GBq/mu mol specific activity at the end of synthesis (EOS). (C) 2010 Elsevier Inc. All rights reserved.
• Synthesis of 2(1H)-Quinolinonequinones and 2-Alkoxyquinolinequinones Using Oxidative Demethylation with Cerium (IV) Ammonium Nitrate
  作者：Yoshiyasu Kitahara、Shinsuke Nakahara、Masaro Shimizu、Takanobu Yonezawa、Akinori Kubo

  DOI：10.3987/com-93-6404

  日期：——

  2,5,8(1H)-Quinolinetriones (12), 2,5,6(1H)-quinolinetriones (13), 2-alkoxy-5,8-quinolinediones (14), 2,8-dimethoxy-5,6-quinolinedione (15), and 2,6-dimethoxy-7,8-quinolinediones (16) were synthesized by oxidative demethylation of the corresponding 2(1H)-quinolinones (7) and 2-alkoxyquinolines (11) with cerium (IV) ammonium nitrate.