3-hydroxy-4-(4-bromophenyl)-N-methylquinolin-2-one | 1134192-65-6

• 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-hydroxy-4-(4-bromophenyl)-N-methylquinolin-2-one
• 英文别名: 4-(4-Bromophenyl)-3-hydroxy-1-methylquinolin-2-one；4-(4-bromophenyl)-3-hydroxy-1-methylquinolin-2-one
• CAS: 1134192-65-6
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 330.181
• InChiKey: CBDLALOFKSVFIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-bromophenyl)-2-cyano-N-methyl-N-phenyloxirane-2-carboxamide 在 硫酸 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以86%的产率得到3-hydroxy-4-(4-bromophenyl)-N-methylquinolin-2-one
  参考文献：
  名称：

  A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides

  摘要：

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

  DOI：

  10.1021/ol900255g

文献信息

• Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro-<i>N</i>,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements
  作者：Vakhid A. Mamedov、Vera L. Mamedova、Zheng-Wang Qu、Hui Zhu、Venera R. Galimullina、Dmitry E. Korshin、Gul’naz Z. Khikmatova、Igor A. Litvinov、Shamil K. Latypov、Oleg G. Sinyashin、Stefan Grimme

  DOI：10.1021/acs.joc.1c01592

  日期：2021.10.1

  duration of the reaction. A combined experimental and DFT mechanistic study of the formation of 1-benzyl-3-hydroxy-4-arylquinolin-2(1H)-ones showed that there are three competing reaction channels: (a) ring-closure via the ipso site, (b) ring-closure via the 1,2-Cl shift, and (c) ring-closure via the ortho site. Such mechanistic insights enabled an effective one-pot gram-scale synthesis of viridicatin

  N -Benzyl-2-chloro - N ,3-diaryloxirane-2-carboxamides 在 Darzens 缩合条件下很容易从二氯乙酸的芳香醛和苯胺中获得，被证明是合成 3-羟基吲哚-2-酮的优良起始化合物, cyclohepto[ b ]pyrrole-2,3-diones 和 1-azaspiro[4.5]deca-3,6,9-triene-2-ones 通过 C(sp 2 )–C(sp 2 ) 键形成第一种情况和 C(sp 2 )–C(sp 3 ) 键在第二种和第三种情况下的形成。在优化的反应条件下，一锅法得到3-羟基吲哚-2-酮，其中包括N-苄基-2-氯-N的处理,3-二芳基环氧乙烷-2-甲酰胺与CF 3 CO 2 H 或AcOH/H 2 SO 4。在分子内环化的情况下，详细的反应通道强烈依赖于存在于苯胺组分和N-苄基-2-氯-N ,3-二芳基环氧乙烷-2-甲
• Surfactant solutions for enhancing solubility of new arylquinolin-2-ones
  作者：Alla B. Mirgorodskaya、Vakhid A. Mamedov、Lucia Ya. Zakharova、Farida G. Valeeva、Vera L. Mamedova、Venera R. Galimullina、Rushana A. Kushnasarova、Oleg G. Sinyashin

  DOI：10.1016/j.molliq.2017.07.055

  日期：2017.9

  Micellar solutions and microemulsions have been used for the increase in the solubility of a series of arylquinolin-2-ones in water. Using spectrophotometry, the solubilization capacity of systems has been characterized with respect to arylquinolin-2-ones. As micelle-forming compounds nonionic amphiphiles are used, whose application is approved in medicinal and pharmacological practice, namely, Tween

  胶束溶液和微乳液已用于增加一系列芳基喹啉-2-酮在水中的溶解度。使用分光光度法，已经相对于芳基喹啉-2-酮表征了系统的增溶能力。作为形成胶束的化合物，使用非离子两亲物，其应用已经在医学和药理学实践中得到批准，即Tween 80，Pluronic F127，Brij 35和Tyloxapol。为了比较，还探索了典型的离子型表面活性剂。已经证明，吐温80的胶束溶液可以将水中测试化合物的含量增加多达20倍，而微乳液表现出更高的效果。已经发现，芳基喹啉-2-酮的增溶过程伴随着其酸碱性质的显着变化：值kа可以由4个单元与来自阳离子表面活性剂的阴离子溶液中的过渡增加。
• Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy
  作者：Vakhid A. Mamedov、Vera L. Mamedova、Saniya F. Kadyrova、Venera R. Galimullina、Gul’naz Z. Khikmatova、Dmitry E. Korshin、Aidar T. Gubaidullin、Dmitry B. Krivolapov、Il’dar Kh. Rizvanov、Olga B. Bazanova、Oleg G. Sinyashin、Shamil K. Latypov

  DOI：10.1021/acs.joc.8b01871

  日期：2018.11.2

  The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring viridicatol, a fungal metabolite isolated from the penicillium species

  描述了一种新的有效的生物重要的3-羟基-4-芳基喹啉-2-酮的有效合成方法，该方法是通过二氯乙苯胺与芳族醛的Darzens缩合（环氧化），然后进行一锅式脱氯环氧-芳烃环化。该方法已用于合成天然存在的维地卡多，这是一种从青霉菌属中分离出来的真菌代谢产物。
• A concise synthesis of indolin-2-ones via direct acid-catalyzed intramolecular Friedel-Crafts alkylation of 3-chloro-N-(substituted)-2-oxo-N,3-diarylpropanamides
  作者：Vakhid A. Mamedov、Venera R. Galimullina、Saniya F. Kadyrova、Il′dar Kh. Rizvanov、Shamil K. Latypov

  DOI：10.1016/j.tetlet.2022.153797

  日期：2022.6

  under Darzens condensation conditions or isomerization of 2-chloro-N,3-diaryloxirane-2-carboxamides, proved to be excellent starting compounds for the synthesis 3-chloro(aryl)methyl)-3-hydroxyindolin-2-ones with the formation of a new C(sp2)–C(sp2)- bond via intramolecular Friedel-Crafts alkylation. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves

  3-Chloro-2- oxo- N ,3-diarylpropanamides，在 Darzens 缩合条件或 2-chloro- N ,3-diaryloxirane-2-carboxamides的异构化条件下很容易从芳香醛和二氯乙酸苯胺中获得，被证明是极好的起始化合物用于通过分子内 Friedel-Crafts 烷基化形成新的 C(sp 2 )-C(sp 2 )- 键合成 3-氯(芳基)甲基)-3-羟基吲哚啉-2-酮。在优化的反应条件下，通过一锅法获得标题化合物，其中包括用 CF 3 CO 2处理N-苄基-3-氯-2-氧代-N ,3-二芳基丙酰胺H. 反应进行时形成易于通过柱色谱分离的反式和顺式非对映体混合物，占前者的 36-49%。
• A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides
  作者：Yusuke Kobayashi、Takashi Harayama

  DOI：10.1021/ol900255g

  日期：2009.4.2

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.