methyl 2-(3,4-dimethoxyphenoxy)benzoate | 101169-58-8

• 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: methyl 2-(3,4-dimethoxyphenoxy)benzoate
• 英文别名: Methyl 2-(3,4-dimethoxyphenoxy)benzoate
• CAS: 101169-58-8
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: BAYHHEUHKZMATI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• 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：

  methyl 2-(3,4-dimethoxyphenoxy)benzoate 在 sodium hydroxide 、 三氯化铝 、 硫酸 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 104.17h， 生成 2,3-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 、 邻溴苯甲酸甲酯 在 铜 、 sodium carbonate 作用下， 以 吡啶 为溶剂， 反应 26.0h， 以41%的产率得到methyl 2-(3,4-dimethoxyphenoxy)benzoate
  参考文献：
  名称：

  Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone

  摘要：

  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.

  DOI：

  10.1107/s010827010101349x

文献信息

• 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.
• ——
  作者：Emília P. Sousa、Artur M. S. Silva、Madalena M. M. Pinto、Madalena M. Pedro、Fátima A. M. Cerqueira、Maria S. J. Nascimento

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

  日期：2002.9

  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.