2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic acid | 281190-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic acid
• CAS: 281190-84-9
• 化学式: C₂₀H₁₆O₇
• 分子量: 368.343
• InChiKey: RCFUHYTVJDDKAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  110.13
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic acid 在 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以79%的产率得到1,8-dimethoxy-3-methyl-7,12-dihydro-5H-dibenzo[c,g]chromene-5,7,12-trione
  参考文献：
  名称：

  Total synthesis of the antibiotic WS-5995A using a key reaction of o-toluamide anions with homophthalic anhydrides.

  摘要：

  抗球虫抗生素 WS-5995A 的全合成是通过将 N,N-二乙基邻甲苯甲酰胺阴离子区域选择性地缩合到苯二甲酐中作为关键反应实现的。

  DOI：

  10.1248/cpb.37.292
• 作为产物：
  描述：

  1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以95%的产率得到2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic 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

• 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.
• WATANABE, MITSUAKI;DATE, MUTSUHIRO;FURUKAWA, SUNAO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 292-297
  作者：WATANABE, MITSUAKI、DATE, MUTSUHIRO、FURUKAWA, SUNAO

  DOI：——

  日期：——