1,2-dimethoxy-9H-xanthen-9-one | 84002-58-4

• 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: 1,2-dimethoxy-9H-xanthen-9-one
• 英文别名: 1,2-dimethoxyxanthone；7,8-dimethoxyxanthone；1,2-dimetoxyxanthone；1,2-dimethoxy-xanthen-9-one；1,2-Dimethoxy-xanthen-9-on；Dimethoxyxanthone；1,2-dimethoxyxanthen-9-one
• CAS: 84002-58-4
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: ONRNUIQDDGNBFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dimethoxy-9H-xanthen-9-one 在 三氯化铝 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 1,2-dihydroxyxanthone
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 sodium hydroxide 、 铜 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 反应 124.0h， 生成 1,2-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r

文献信息

• Intramolecular Anionic Friedel-Crafts Equivalents. A General Regiospecific Route to Substituted and Naturally Occurring Xanthen-9-ones
  作者：O. Familoni、Ileana Ionica、Justin Bower、Victor Snieckus

  DOI：10.1055/s-1997-1533

  日期：1997.9

  An LDA-induced regiospecific and general conversion of diaryl ether 2-carboxamides 4 into substituted xanthones 5, including natural products, 2-hydroxy-1-methoxyxanthone (8) and 6-deoxy-jacareubin (14), is described.

  报道了一种由线性判别分析诱导的、对二芳基醚2-羧酰胺4的区域特异性及普遍性转化，生成取代咕吨酮5，包括天然产物2-羟基-1-甲氧基咕吨酮(8)和6-脱氧雅卡尔宾(14)。
• Davies et al., Journal of the Chemical Society, 1958, p. 1790,1793
  作者：Davies et al.

  DOI：——

  日期：——
• Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone
  作者：Luis Gales、Maria Emilia de Sousa、Madalena M. M. Pinto、Anake Kijjoa、Ana M. Damas

  DOI：10.1107/s010827010101349x

  日期：2001.11.15

  In order to study structure-activity relationships, a series of mono-, di- and trioxygenated xanthones has been synthesized and the structures of methyl 2-(3,4-dimethoxyphenoxy)benzoate, C16H16O5, 2-(3,4-dimethoxyphenoxy)benzoic acid, C15H14O5, 1,2-dimethoxy-9H-xanthen-9-one, C15H12O4, and 1,2,8-trimethoxy-9H-xanthen-9-one, C16H14O5, have been determined. The first two compounds both assume skew conformations, the dihedral angles between the two phenyl rings being 80.04 (8) and 83.0 (1)degrees, respectively. The latter two compounds are essentially planar and their methoxy substituents assume orientations consistent with minimum steric interactions.
• Xanthones as inhibitors of growth of human cancer cell lines and Their effects on the proliferation of human lymphocytes In Vitro
  作者：Madalena Pedro、Fátima Cerqueira、Maria Emı́lia Sousa、Maria São José Nascimento、Madalena Pinto

  DOI：10.1016/s0968-0896(02)00379-6

  日期：2002.12

  Twenty-seven oxygenated xanthones have been assessed for their capacity to inhibit in vitro the growth of three human cancer cell lines, MCF-7 (breast cancer). TK-10 (renal cancer) and UACC-62 (melanoma). The effect of these xanthones on the proliferation of human T-lymphocytes was also evaluated. Differences on their potency towards the effect on the growth of the human cancer cell lines as well as on the proliferation of human T-lymphocytes can be ascribed to the nature and positions of the substituents on the xanthonic nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.
• CONTROLLED SHRINKAGE ULTRAVIOLET LIGHT RESISTANT MOLDING COMPOUND
  申请人：Guha Probir K.

  公开号：US20070197694A1

  公开（公告）日：2007-08-23

  A molding composition formulation is provided that includes a thermoset cross-linkable polymeric resin and an ultraviolet light absorber. A shrinkage-reducing polymeric additive is present in the formulation from between 3 and 30 total weight percent, such that upon cure a linear shrinkage rate of within ±1.0% is obtained. Shrinkage-reducing polymeric additives include a condensation polyester of glycol and a polyacid or acid anhydride, polyvinyl acetate, polymethylmethacrylate, or polyether polyol. A vehicle body component formed through a sheet molding composition formulation is provided as recited above, and includes a fiberglass filler. A process for producing a vehicle body component exposed to ultraviolet light upon environmental exposure of a vehicle includes molding at an elevated temperature above 20° C. the vehicle component from the formulation as detailed above. The process is followed by trimming the molded vehicle component prior to assembly.