3-hydroxy-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione | 369651-50-3

• 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: 3-hydroxy-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione
• 英文别名: 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione；3-hydroxy-3-methyl-1-phenylquinoline-2,4-dione
• CAS: 369651-50-3
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: GWOAPMBNZFGLSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione 在 氢氧化钾 、 air 作用下， 以 苯 为溶剂， 反应 0.5h， 以52%的产率得到2-hydroxy-2-methyl-1-phenyl-1,2-dihydro-3H-indol-3-one
  参考文献：
  名称：

  Novel Ring Contraction of 3-Hydroxy-2,4(1H,3H)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls

  摘要：

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.

  DOI：

  10.1021/jo015786d
• 作为产物：
  描述：

  4-hydroxy-1-phenyl-3-methyl-1H-quinolin-2-one 在 过氧乙酸 作用下， 生成 3-hydroxy-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione
  参考文献：
  名称：

  Novel Ring Contraction of 3-Hydroxy-2,4(1H,3H)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls

  摘要：

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.

  DOI：

  10.1021/jo015786d

文献信息

• Limitations of the Wittig–Horner-type annulation of fluorobutenolide moiety to 3-hydroxyquinoline-2,4(2H,3H)-diones. Novel modifications of the Perkow reaction including fluorinated acyloxy leaving groups
  作者：Karel Pomeisl、Jaroslav Kvíčala、Oldřich Paleta、Antonín Klásek、Stanislav Kafka、Vladislav Kubelka、Jaroslav Havlíček、Jan Čejka

  DOI：10.1016/j.tet.2007.07.058

  日期：2007.10

  3-(Fluoroacyloxy)quinoline-2,4(1H,3H)-diones react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the leaving group. For the corresponding 3-(fluoroiodoacetoxy) derivative this observation precludes the application of the intramolecular Wittig–Horner synthesis to modify

  3-（氟酰氧基）喹啉-2,4（1 H，3 H）-二酮与亚磷酸三乙酯反应，得到Perkow反应的产物或相应的4-乙氧基喹啉-2（1 H）-一。在两个反应中，氟代羧酸根阴离子都作为离去基团。对于相应的3-（氟碘乙酰氧基）衍生物，该观察结果排除了分子内Wittig-Horner合成方法的应用，该方法是通过氟化丁-2-烯内酯部分的环化来修饰喹啉-2,4（1 H，3 H）-二酮。
• Reaction of Tertiary 2‐Chloroketones with Cyanide Ions: Application to 3‐Chloroquinolinediones
  作者：Antonín Klásek、Stanislav Kafka、Ondřej Rudolf、Antonín Lyčka、Michal Rouchal、Lukáš Bednář

  DOI：10.1002/open.202100024

  日期：2021.6

  3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position is the methyl group. In the methanol solution, the reaction proceeds by an addition mechanism to form 2-oxo-1a,2,3,7b-tetrahydrooxireno[2,3-c]qui

  3-氯喹啉-2,4-二酮与氰化物离子在二甲基甲酰胺中反应生成3-氰基喹啉-2,4-二酮，由于C-3原子上取代基的强烈位阻，产率较低。如果该位置的取代基是甲基，则可以获得良好的产率。在甲醇溶液中，反应通过加成机制进行，形成2-氧代-1a,2,3,7b-四氢氧并[2,3 -c ]喹啉-7b-甲腈，其中4-羟基-3-甲氧基-随后通过用甲醇打开环氧化物环形成2-氧代-1,2,3,4-四氢喹啉-4-甲腈。这些反应的一些次要产物也已被分离出来。测量所制备的化合物的1 H、 13 C 和15 N NMR 谱，并使用适当的二维谱分配所有共振。
• Formation and structure elucidation of two novel spiro[2H-indol]-3(1H)-ones
  作者：Janez Košmrlj、Stanislav Kafka、Ivan Leban、Marjeta Grad

  DOI：10.1002/mrc.2028

  日期：2007.8

  The molecular structures of two byproducts 1,1″‐diphenyl‐3′,4′‐dihydrodispiro[indole‐2,2′‐furan‐5′,2″‐indole]‐3,3″(1H, 1″H)‐dione (3) and 1,5′‐diphenyl‐4′,5′‐dihydro‐3′H‐spiro[indole‐2,2′‐pyrano[3,2‐b]indol]‐3(1H)‐one (4), which accompanied the rearrangement of 3‐hydroxy‐3‐methyl‐1‐phenylquinoline‐2,4(1H,3H)‐dione (1) to 2‐hydroxy‐2‐methyl‐1‐phenyl‐1,2‐dihydro‐3H‐indol‐3‐one (2), have been elucidated

  两种副产物 1,1"-diphenyl-3',4'-dihydrodispiro[indole-2,2'-furan-5',2"-indole]-3,3"(1H, 1"H) 的分子结构-dione (3) 和 1,5'-diphenyl-4',5'-dihydro-3'H-spiro[indole-2,2'-pyrano[3,2-b]indol]-3(1H)-一 (4)，伴随着 3-羟基-3-甲基-1-苯基喹啉-2,4(1H,3H)-二酮 (1) 重排为 2-羟基-2-甲基-1-苯基-1， 2-dihydro-3H-indol-3-one (2)，已通过 NMR、MS 和 X 射线衍射阐明。版权所有 © 2007 John Wiley & Sons, Ltd.
• Novel Ring Contraction of 3-Hydroxy-2,4(1<i>H</i>,3<i>H</i>)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls
  作者：Stanislav Kafka、Antonín Klásek、Janez Košmrlj

  DOI：10.1021/jo015786d

  日期：2001.9.1

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.