2-acetyl-3-methoxyphenyl acetate | 135831-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-3-methoxyphenyl acetate
• 英文别名: 2'-Hydroxy-6'-methoxyacetophenone, acetate；(2-acetyl-3-methoxyphenyl) acetate
• CAS: 135831-50-4
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: FMVANFQMWMZTSB-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  324.5±32.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)
• 保留指数：
  1559.8

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-methoxyphenyl acetate 在 potassium tert-butylate 作用下， 生成 1-(2-羟基-6-甲氧基苯基)-1,3-丁二酮
  参考文献：
  名称：

  Synthesis and biological evaluation of flavonoids and related compounds as gastroprotective agents

  摘要：

  Several analogs of the gastroprotective molecule flavone have been synthesized and evaluated for gastroprotective activity. A C2-C3 double bond and an intact C ring appear necessary for optimum activity. Activity can be retained by replacing the 2-phenyl substituent with other groups but is eliminated when this ring is moved from the 2- to the 3-position. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00134-5
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.33h， 生成 2-acetyl-3-methoxyphenyl acetate
  参考文献：
  名称：

  新型色酮和x吨酮衍生物：合成和ROS / RNS清除活性。

  摘要：

  苯醌和氧杂蒽酮是含氧杂环化合物，因其抗氧化性能而得到认可。为了开发具有改善的活性的新型试剂，制备了一系列属于这些化学类别的化合物。它们的合成涉及通过Baker-Venkataraman重排获得的合适的2-甲基-4H-chromen-4-one与（E）-3-（3,4-二甲氧基苯基）丙烯醛的缩合反应提供相应的2-[（（1E） ，3E）-4-（3,4-二甲氧基苯基）buta-1,3-dien-1-yl] -4H-chromen-4-ones。这些化合物的随后的电环化和氧化作用导致了1-芳基-9H-黄嘌呤-9-酮的合成。切割保护基团后，评估了羟基化的色酮和氧杂蒽类作为对两种活性氧（ROS）[超氧自由基（O2 *-），过氧化氢（H2O2），次氯酸（HOCl），单线态氧（1O2）和过氧自由基（ROO *）]和活性氮物质（RNS）[一氧化氮（* NO）和过氧亚硝酸盐阴离子（ONOO-）]。通常，所有测试

  DOI：

  10.1016/j.ejmech.2016.03.043

文献信息

• Chemical model studies on the mutagenesis of benzofuran dioxetanes in the Ames test: evidence for the benzofuran epoxide as ultimate mutagen
  作者：W. Adam、L. Hadjiarapoglou、T. Mosandl、C. R. Saha-Moeller、D. Wild

  DOI：10.1021/ja00021a029

  日期：1991.10

  The synthesis of the first benzofuran epoxide 3a was achieved by epoxidation of the benzofuran 1a with dimethyldioxirane and alternatively by deoxygenation of the benzofuran dioxetane 2a with sulfides. This labile epoxide formed with nucleophiles such as water, methanol, thiophenol, and imidazole the corresponding adducts 13a-16a. In contrast to epoxide 3a, the dioxetanes 2 required acid catalysis (CF3CO2H) for the addition of water, methanol, and azide ion to give the corresponding adducts 9-11; in the absence of nucleophiles the allylic hydroperoxides 8 were formed. The decomposition of benzofuran dioxetanes 2 in the polar, protic solvents water and methanol afforded not only expected cleavage products 4 but also the 1,3-dioxols 5, the spiroepoxide dimer 6a, and the 1,4-dioxines 7. An intramolecular electron-transfer mechanism is postulated for the formation of the spiroepoxide, which subsequently dimerizes to 6a or rearranges into 5 and 7. Only the benzofuran epoxide 3a, besides the benzofuran dioxetanes 2, was mutagenic in the Salmonella typhimurium strain TA100. Therefore, we implicate the epoxide 3a as the ultimate mutagen responsible for the high mutagenic activity observed with dioxetane 2a in the Ames test. We postulate that in the oxidative metabolism of polycyclic arenes and heteroarenes the corresponding epoxides are generated from the intermediary dioxetanes by deoxygenation with sulfides.
• Naik; Thakor, Proceedings - Indian Academy of Sciences, Section A, 1953, vol. 37, p. 774,781
  作者：Naik、Thakor

  DOI：——

  日期：——
• Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities
  作者：Carina Proença、Hélio M.T. Albuquerque、Daniela Ribeiro、Marisa Freitas、Clementina M.M. Santos、Artur M.S. Silva、Eduarda Fernandes

  DOI：10.1016/j.ejmech.2016.03.043

  日期：2016.6

  cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O2*-), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen (1O2), and peroxyl radical (ROO*)] and reactive nitrogen species (RNS) [nitric oxide (*NO) and peroxynitrite anion (ONOO-)]. Generally, all the tested new hydroxylated

  苯醌和氧杂蒽酮是含氧杂环化合物，因其抗氧化性能而得到认可。为了开发具有改善的活性的新型试剂，制备了一系列属于这些化学类别的化合物。它们的合成涉及通过Baker-Venkataraman重排获得的合适的2-甲基-4H-chromen-4-one与（E）-3-（3,4-二甲氧基苯基）丙烯醛的缩合反应提供相应的2-[（（1E） ，3E）-4-（3,4-二甲氧基苯基）buta-1,3-dien-1-yl] -4H-chromen-4-ones。这些化合物的随后的电环化和氧化作用导致了1-芳基-9H-黄嘌呤-9-酮的合成。切割保护基团后，评估了羟基化的色酮和氧杂蒽类作为对两种活性氧（ROS）[超氧自由基（O2 *-），过氧化氢（H2O2），次氯酸（HOCl），单线态氧（1O2）和过氧自由基（ROO *）]和活性氮物质（RNS）[一氧化氮（* NO）和过氧亚硝酸盐阴离子（ONOO-）]。通常，所有测试
• Synthesis and biological evaluation of flavonoids and related compounds as gastroprotective agents
  作者：Jeffrey J. Ares、Pamela E. Outt、Jared L. Randall、Jeffrey N. Johnston、Peter D. Murray、Linda M. O'Brien、Pamela S. Weisshaar、Beth L. Ems

  DOI：10.1016/0960-894x(96)00134-5

  日期：1996.4

  Several analogs of the gastroprotective molecule flavone have been synthesized and evaluated for gastroprotective activity. A C2-C3 double bond and an intact C ring appear necessary for optimum activity. Activity can be retained by replacing the 2-phenyl substituent with other groups but is eliminated when this ring is moved from the 2- to the 3-position. Copyright (C) 1996 Elsevier Science Ltd