2-(3-hydroxy-1,4-dioxo-1,4-dihydro-2-naphthlenyl)benzoic acid | 94502-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-hydroxy-1,4-dioxo-1,4-dihydro-2-naphthlenyl)benzoic acid
• 英文别名: 2-(3-hydroxy-1,4-dioxo-1,4-dihydro-[2]naphthyl)-benzoic acid；2-(3-Hydroxy-1,4-dioxo-1,4-dihydro-[2]naphthyl)-benzoesaeure；2-Hydroxy-3-<2-carboxy-phenyl>-1,4-naphthochinon；2-Hydroxy-3-(2'-carboxy-phenyl)-1,4-naphthochinon
• CAS: 94502-33-7
• 化学式: C₁₇H₁₀O₅
• 分子量: 294.263
• InChiKey: GYOQYTBRAGOUMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.67
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-1,4-dioxo-1,4-dihydro-2-naphthlenyl)benzoic acid 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到11,12-dihydro-6H-dibenzo[c,h]chromene-6,11,12-trione
  参考文献：
  名称：

  Annulation Strategies for Benzo[b]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.

  DOI：

  10.1021/jo0056186
• 作为产物：
  描述：

  12-methoxy-6H-benzo[d]naphtha[1,2-b]pyran-6-one 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以65%的产率得到2-(3-hydroxy-1,4-dioxo-1,4-dihydro-2-naphthlenyl)benzoic acid
  参考文献：
  名称：

  Annulation Strategies for Benzo[b]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.

  DOI：

  10.1021/jo0056186

文献信息

• Ru(II)-Catalyzed [4 + 2]-Annulation and Arylation of 1,4-Naphthoquinones
  作者：Shreemoyee Kumar、Akshay M. Nair、Jatin Patra、Chandra M. R. Volla

  DOI：10.1021/acs.orglett.3c00033

  日期：2023.2.24

  4-naphthoquinones with organic building blocks would offer a facile strategy toward scaffolds of biological interest. In this regard, we hereby report a Ru(II)-catalyzed [4 + 2] annulation of 1,4-naphthoquinones with benzoic acids to afford various naphthoquinone lactones. Additionally, ketone directed arylation of naphthoquinones using acetophenones under Ru(II)-catalysis was also illustrated. The feedstock

  萘醌是多种药物和天然产物的核心。因此，1,4-萘醌与有机结构单元的结合将为具有生物学意义的支架提供一种简便的策略。在这方面，我们在此报告了 Ru(II) 催化的 1,4-萘醌与苯甲酸的 [4 + 2] 环化反应，得到了各种萘醌内酯。此外，还说明了在 Ru(II) 催化下使用苯乙酮对萘醌进行酮定向芳基化。这些前体的原料可用性允许在相当温和的条件下以良好到极好的收率访问大型萘醌衍生物库。通过进行克级合成和进一步功能化，证明了这些协议的实用性。还，
• Neunhoeffer; Weise, Chemische Berichte, 1938, vol. 71, p. 2703,2707
  作者：Neunhoeffer、Weise

  DOI：——

  日期：——
• Regioselective lactonization of naphthoquinones: synthesis and antitumoral activity of the WS-5995 antibiotics
  作者：Ghassan Qabaja、Elisabeth M. Perchellet、Jean-Pierre Perchellet、Graham B Jones

  DOI：10.1016/s0040-4039(00)00329-4

  日期：2000.4

  An acid promoted quinolactonization of naphthoquinones has been developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C and functional analogs is demonstrated. Preliminary antitumoral activity of the analogs is presented together with electrochemical analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.