4-羟基-1,6-二甲基-2(1H)-喹啉酮 | 54675-24-0

• 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
• 中文名称: 4-羟基-1,6-二甲基-2(1H)-喹啉酮
• 英文名称: 1,6-dimethyl-4-hydroxy carbostyril
• 英文别名: 4-hydroxy-1,6-dimethyl-1H-quinolin-2-one；4-Hydroxy-1,6-dimethylquinolin-2(1H)-one；4-hydroxy-1,6-dimethylquinolin-2-one
• CAS: 54675-24-0
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD01101046
• 分子量: 189.214
• InChiKey: VZOOIPFSWSMDRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-羟基-1,6-二甲基-2(1H)-喹啉酮 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 magnesium(II) perchlorate 、 sodiumsulfide nonahydrate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 5,8-dimethyl-2-phenylthieno[2,3-c]quinolin-4(5H)-one
  参考文献：
  名称：

  Access to Functionalized 3H-Pyrrolo[2,3-c]quinolin-4(5H)-ones and Thieno[2,3-c]quinolin-4(5H)-ones via Domino Reaction of 4-Alkynyl-3-bromoquinolin-2(1H)-ones

  摘要：

  We describe two efficient protocols for the straightforward synthesis of 3H-pyrrolo[2,3-c]quinolin-4(SH)-one and thieno[2,3-c]quinolin-4(SH)-one derivatives from readily a].abllie4-4 Yalkyn-3-bromoquinolin-2(1H)-one as precursor. The efficient synthesis of highly functionalized 3H-pyrrolo[2,3-c (SH)-ones has been achieved via a palladium-catalyzed domino reaction of 4-alkyny1-3-bromoquinolin-2(11-1)-ones wilum n_ hines. Thieno[2,3-c]quinolin-4(SH)-one derivatives were also conveniently synthesized via sequential nucleophilic aromatic substitution/S-endo-dig cydization between 4-alkyny1-3bromoquinolin-2(1H)-ones and sodium sulfide with good functional tolerance under mild Conditions.

  DOI：

  10.1021/jo501753p

文献信息

• Copper-Mediated Direct Sulfenylation of 4-Hydroxyquinolinones and 4-Hydroxypyridones with Aryl Thiols via a C−H Functionalization Process
  作者：Tao Guo、Hongyan Wang

  DOI：10.1055/s-0036-1588829

  日期：2017.9

  An efficient approach for the direct sulfanylation of 4-hydroxyquinolinones and 4-hydroxypyridones with aryl thiols in the presence of CuI/DMSO has been developed. The substrate scope is broad, allowing facile synthesis of a range of structurally diverse 3-sulfanyl-4-hydroxyquinolinones and 3-sulfanyl-4-hydroxypyridones in good efficiency.

  一种在CuI/DMSO存在下，利用芳基硫醇直接对4-羟基喹啉酮和4-羟基吡啶酮进行砜化的高效方法已经开发出来。底物范围广泛，能够轻松合成一系列结构多样的3-砜基-4-羟基喹啉酮和3-砜基-4-羟基吡啶酮，效率良好。
• An efficient route to diverse 2H-pyrano[3,2-c]quinolin-5(6H)-ones via electrophilic cyclization reactions
  作者：Zhen Chen、Zhiyong Wang

  DOI：10.1016/j.tet.2016.05.075

  日期：2016.7

  Electrophilic cyclization of 4-((3-arylprop-2-yn-1-yl)oxy)quinolin-2(1H)-one derivatives with iodine leads to the formation of 2H-pyrano[3,2-c]quinolin-5(6H)-ones bearing an alkenyl iodide moiety in good to excellent yields under mild conditions. The resulting iodo-containing 2H-pyrano[3,2-c]quinolin-5(6H)-ones could be further elaborated via palladium-catalyzed cross-coupling reactions.

  4-（（3-芳基-2--2--1-氧基）喹啉-2（1 H）-one衍生物与碘的亲电环化反应导致2 H-吡喃并[3,2- c ]喹啉的形成在温和的条件下，具有良好产率的-5（6 H）-烯基碘化物部分。所得的含碘的2 H-吡喃并[3,2 - c ]喹啉-5（6 H）-酮可通过钯催化的交叉偶联反应进一步加工。
• Ammonium Iodide-Mediated Sulfenylation of 4-Hydroxycoumarins or 4-Hydroxyquinolinones with a Sulfonyl Chloride as a Sulfur Source
  作者：Tao Guo、Xu-Ning Wei

  DOI：10.1055/s-0036-1589083

  日期：2017.11

  A novel ammonium iodide-induced sulfenylation of 4-hydroxycoumarins or 4-hydroxyquinolinones by using an aryl- or alkylsulfonyl chloride as the sulfur source gave a wide range of 3-sulfanyl-4-hydroxycoumarins or 3-sulfanyl-4-hydroxyquinolinones, respectively, in moderate to good yields. This method provides as a simple approach to the direct formation of C–S bonds, which is of high value and utility

  通过使用芳基-或烷基磺酰氯作为硫源，碘化铵诱导的 4-羟基香豆素或 4-羟基喹啉酮的新型磺酰化分别得到了广泛的 3-硫烷基-4-羟基香豆素或 3-硫烷基-4-羟基喹啉酮，中等至良好的产量。这种方法提供了一种直接形成 C-S 键的简单方法，在制药行业中具有很高的价值和实用性。
• Palladium-catalyzed facile synthesis of furoquinolinones and furopyridinones
  作者：Tao Guo、Xu-Ning Wei、Hong-Yan Wang、Bing Zhao

  DOI：10.1080/00397911.2017.1422519

  日期：2018.4.3

  ABSTRACT This work is focused on the development of a convenient and efficient approach for the synthesis of furoquinolinones and furopyridinones through palladium-catalyzed cyclization reactions between styrenes and 4-hydroxyquinolinones/4-hydroxypyridinones under air conditions. Studies conducted to evaluate the antitumoral potential of the resulted compounds revealed that some of the obtained furoquinolinones

  摘要这项工作的重点是开发一种方便有效的方法，通过钯催化苯乙烯和 4-羟基喹啉酮/4-羟基吡啶酮在空气条件下的环化反应合成呋喃喹啉酮和呋喃吡啶酮。为评估所得化合物的抗肿瘤潜力而进行的研究表明，一些获得的呋喃喹啉酮在体外对人源胃癌细胞系具有抗增殖活性。图形概要
• Anti-allergenic carbostyril derivatives
  申请人：Beecham Group Limited

  公开号：US03962445A1

  公开（公告）日：1976-06-08

  A class of 4-hydroxy-3-nitroearbostyril derivatives are useful in the inhibition of certain types of antigen antibody reactions.

  一类4-羟基-3-硝基耳波斯蒂尔衍生物在抑制特定类型的抗原抗体反应中很有用。