1,3,5-trimethoxy-9H-xanthen-9-one | 6563-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3,5-trimethoxy-9H-xanthen-9-one
• 英文别名: 1,3,5-trimethoxyxanthone；1,3,5-trimethoxy-xanthen-9-one；1,3,5-Trimethoxy-xanthen-9-on；1,3,5-Trimethoxy-xanthon；1,3,5-Trimethoxyxanthon；1,3,5-trimethoxyxanthen-9-one
• CAS: 6563-50-4
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: RZTTWIXYIUTQIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,5-trimethoxy-9H-xanthen-9-one 在 氢氧化钾 、 氢碘酸 、 氧气 、 tetraphenylporphyrin 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 6-去氧异巴西红厚壳素
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

  摘要：

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.033
• 作为产物：
  描述：

  3-甲氧基水杨酸 在 potassium carbonate 、 丙酮 、 zinc(II) chloride 、 三氯氧磷 作用下， 生成 1,3,5-trimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Kane et al., Journal Of Scientific and Industrial Research, 1959, vol. 18 B, p. 28,30

  摘要：

  DOI：

文献信息

• γ-Pyrone Compounds as Potential Anti-cancer Drugs
  作者：Shorong-Shii Liou、Wen-Liang Shieh、Tien-Hsiang Cheng、Shen-Jeu Won、Chun-Nan Lin

  DOI：10.1111/j.2042-7158.1993.tb05686.x

  日期：2011.4.12

  The γ-pyrones, artomunoxanthotrione epoxide, cyclocommunol, cyclomulberrin, and cyclocommunin exhibited potent inhibition of human PLC/PRF/5 and KB cells in-vitro. Dihydroisocycloartomunin showed significant and potent inhibition of human PLC/PRF/5 and KB cells in-vitro, respectively. Cyclomorusin, dihydrocycloartomunin and artomunoxanthone showed significant inhibition of KB cells in-vitro. Based on the above finding and the reported antileukaemic activity of xanthone psorospermin, a series of natural γ-pyrones was prepared and the inhibition of human PLC/PRF/5 and KB cells in-vitro was measured. Structure-activity analysis indicated the epoxide group substituted at 3-hydroxyl and 2,6-; 3,6-; and 3,5-dihydroxyl xanthone enhanced the anti-tumour activity. The epoxide group substituted at the 6-hydroxyl group of 1,6-dihydroxyxanthone did not show anti-tumour activity.

  γ-吡喃酮类化合物，包括artomunoxanthotrione环氧化物、cyclocommunol、cyclomulberrin和cyclocommunin在体外表现出对人类PLC/PRF/5和KB细胞的强效抑制作用。Dihydroisocycloartomunin在体外对人类PLC/PRF/5和KB细胞分别表现出显著和强效的抑制作用。Cyclomorusin、dihydrocycloartomunin和artomunoxanthone在体外对KB细胞表现出显著的抑制作用。基于上述发现和报道的黄酮类化合物psorospermin的抗白血病活性，制备了一系列天然γ-吡喃酮类化合物，并测量了其在体外对人类PLC/PRF/5和KB细胞的抑制作用。结构活性分析表明，取代3-羟基和2,6-；3,6-；和3,5-二羟基黄酮的环氧化物基团增强了抗肿瘤活性。1,6-二羟基黄酮的6-羟基处取代的环氧化物基团没有显示出抗肿瘤活性。
• Compounds for the treatment of hepatoma
  申请人：National Science Council

  公开号：US05741813A1

  公开（公告）日：1998-04-21

  Compounds of general Formula I in which the substituents of R.sub.1 -R.sub.7 are hydrogen, hydroxy group, C.sub.1-6 alkyl group, C.sub.1-6 alkoxy group, or epoxypropoxy, but at the most, six of the substituents can simultaneously be hydrogen, methoxy group, or hydroxy group, or epoxypropoxy group for activity against hepatoma. There are also described processes for the preparation of the novel compounds and useful intermediates. Substitute benzophenones are described.

  通式I的化合物中，R.sub.1-R.sub.7的取代基为氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或环氧丙氧基，但最多只有六个取代基可以同时为氢、甲氧基或羟基，或环氧丙氧基，用于对抗肝癌的活性。还描述了制备新化合物和有用中间体的过程。还描述了取代苯甲酮。
• Microwave‐Assisted Xanthone Synthesis
  作者：E. A. Evangelista、M. R. C. Couri、R. B. Alves、D. S. Raslan、R. P. F. Gil

  DOI：10.1080/00397910600639653

  日期：2006.8

  Xanthones have been prepared by microwave irradiation-assisted cyclization of 2-hydroxy-2'-methoxy benzophenone precursors in a short time and good yields.
• US5741813A
  申请人：——

  公开号：US5741813A

  公开（公告）日：1998-04-21
• US5919779A
  申请人：——

  公开号：US5919779A

  公开（公告）日：1999-07-06