3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one | 1134192-59-8

• 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-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one
• 英文别名: 3-Hydroxy-1-[(4-methoxyphenyl)methyl]-4-phenylquinolin-2-one
• CAS: 1134192-59-8
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: XHRSPIWQIXLMJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one 在 硫酸 作用下， 以 苯甲醚 、 三氟乙酸 为溶剂， 反应 24.0h， 以73%的产率得到纯绿青霉素
  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
• 作为产物：
  描述：

  在 硫酸 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以775 mg的产率得到3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-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
• 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.