1-[4-(sec-butoxy)-2-hydroxyphenyl]ethanone | 714960-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(sec-butoxy)-2-hydroxyphenyl]ethanone
• 英文别名: 1-(4-(sec-butoxy)-2-hydroxyphenyl)ethan-1-one；1-(4-Butan-2-yloxy-2-hydroxyphenyl)ethanone
• CAS: 714960-80-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: MVVHCGUBQGPMGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(sec-butoxy)-2-hydroxyphenyl]ethanone 在 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 二苯醚 、 xylene 为溶剂， 反应 1.5h， 生成 7-(sec-butoxy)-4-chloro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins

  摘要：

  Pursuing our chemical and biological studies in this field, we described the multistep preparation of the new 5-, 6-, or 7-alkoxy and 7-alkoxy-8-methyl substituted 4-(1-piperazinyl)coumarins 5d-v, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187. Compounds 5h-j,p,r-u showed notably high activity towards all the platelet aggregation inducers used, and the most active one, 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin (5t), proved to be a potent in vitro antiplatelet agent. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.010
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 2-碘丁烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 6.0h， 以65%的产率得到1-[4-(sec-butoxy)-2-hydroxyphenyl]ethanone
  参考文献：
  名称：

  Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins

  摘要：

  Pursuing our chemical and biological studies in this field, we described the multistep preparation of the new 5-, 6-, or 7-alkoxy and 7-alkoxy-8-methyl substituted 4-(1-piperazinyl)coumarins 5d-v, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187. Compounds 5h-j,p,r-u showed notably high activity towards all the platelet aggregation inducers used, and the most active one, 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin (5t), proved to be a potent in vitro antiplatelet agent. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.010

文献信息

• Regioselective alkylation of 2,4-dihydroxybenzyaldehydes and 2,4-dihydroxyacetophenones
  作者：Aziza Frank、Negar Hamidi、Fengtian Xue

  DOI：10.1016/j.tetlet.2022.153755

  日期：2022.4

  We report a cesium bicarbonate-mediated alkylation of 2,4-dihydroxybenzyaldehyde and 2,4-dihydroxyacetophenone to generate 4-alkylated products in acetonitrile at 80 °C with excellent regioselectivity, up to 95% isolated yields, and broad substrate scope.

  我们报道了碳酸氢铯介导的 2,4-二羟基苯甲醛和 2,4-二羟基苯乙酮的烷基化反应，在 80 °C 的乙腈中生成 4-烷基化产物，具有优异的区域选择性、高达 95% 的分离产率和广泛的底物范围。