4-hydroxy-8-methoxy-1-methylquinolin-2(1H)-one | 3148-27-4

• 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: 4-hydroxy-8-methoxy-1-methylquinolin-2(1H)-one
• 英文别名: 4-hydroxy-8-methoxy-N-methylquinolin-2(1H)-one；4-Hydroxy-8-methoxyquinolin-2-one；4-hydroxy-8-methoxy-1-methyl-1H-quinolin-2-one；4-hydroxy-8-methoxy-1-methyl-2(1H)-quinolinone；4-hydroxy-8-methoxy-1-methylquinolin-2-one
• CAS: 3148-27-4
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: IHANDTHWZGLKJW-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C
• 沸点：
  347.7±42.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-8-methoxy-1-methylquinolin-2(1H)-one 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 4-hydroxy-8-methoxy-N-methyl-3-(3-methylbut-3-enyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Bravo, Pierfrancesco; Resnati, Giuseppe; Viani, Fiorenza, Journal of Chemical Research, Miniprint, 1986, # 10, p. 3250 - 3264

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基-N-甲基苯胺 在 甲烷磺酸 、 四磷十氧化物 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 4-hydroxy-8-methoxy-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040

文献信息

• Asymmetric Total Synthesis and Biological Evaluation of the Natural PDE4 Inhibitor Toddacoumalone
  作者：Ke-Qiang Hou、Xue-Ping Chen、Yiyou Huang、Albert S. C. Chan、Hai-Bin Luo、Xiao-Feng Xiong

  DOI：10.1021/acs.orglett.9b04355

  日期：2020.1.17

  We describe herein the first asymmetric total synthesis and biological evaluation of the natural PDE4 inhibitor toddacoumalone and its stereoisomers. The key step of the total synthesis is a formal asymmetric [4 + 2] cycloaddition reaction catalyzed by chiral secondary amine catalysts. A variety of pyranoquinolinones and 3-methylcrotonaldehyde are well tolerated under the optimized reaction conditions

  我们在本文中描述了天然PDE4抑制剂toddacoumalone及其立体异构体的首次不对称总合成和生物学评估。全合成的关键步骤是由手性仲胺催化剂催化的形式不对称[4 + 2]环加成反应。在优化的反应条件下，多种吡喃喹啉酮和3-甲基巴豆醛具有良好的耐受性，为进一步的SAR研究铺平了道路。进一步的生物学评估显示1a'具有最佳的PDE4抑制活性（IC50 = 0.18μM）。
• One-step formation of furo[3,2-c]quinolin-4(5H)-ones by a new regioselective [2+3] photoaddition of methoxy-substituted 4-hydroxyquinolin-2-one with alkenes1
  作者：Hiroshi Suginome、Shinzo Seko、Atsushi Konishi、Kazuhiro Kobayashi

  DOI：10.1016/s0040-4039(00)93442-7

  日期：1991.9

  Furo[3,2-c]quinolin-4(5H)-ones carrying one or more methoxyl group at their 5, 6, or 8 position can be obtained in yields of up to 60% using a one-step procedure involving an unprecedented [2+3] photoaddition between 5-, 7-, or 8-methoxy-4-hydroxyquinolin-2-one and an alkene in the presence of a benzophenone.
• BRAVO P.; RESNATI G.; VIANI F.; CAVICCHIO G., J. CHEM. RES. SYNOP., # 10,(1986) N 10, 374-375
  作者：BRAVO P.、 RESNATI G.、 VIANI F.、 CAVICCHIO G.

  DOI：——

  日期：——
• Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin
  作者：Jian Li、Qi-Long Hu、Xue-Ping Chen、Ke-Qiang Hou、Albert S.C. Chan、Xiao-Feng Xiong

  DOI：10.1016/j.cclet.2019.08.040

  日期：2020.3

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Bravo, Pierfrancesco; Resnati, Giuseppe; Viani, Fiorenza, Journal of Chemical Research, Miniprint, 1986, # 10, p. 3250 - 3264
  作者：Bravo, Pierfrancesco、Resnati, Giuseppe、Viani, Fiorenza、Cavicchio, Giancarlo

  DOI：——

  日期：——