2-acetyl-5-(2-phenylethoxy)phenol | 63359-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-5-(2-phenylethoxy)phenol
• 英文别名: 1-(2-hydroxy-4-phenethoxyphenyl)ethan-1-one；1-[2-Hydroxy-4-(2-phenylethoxy)phenyl]ethan-1-one；1-[2-hydroxy-4-(2-phenylethoxy)phenyl]ethanone
• CAS: 63359-84-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: YZSINMPTPUSMRM-UHFFFAOYSA-N

物化性质

• 熔点：
  69°C
• 沸点：
  442.3±35.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-acetyl-5-(2-phenylethoxy)phenol 在 吡啶 、 potassium tert-butylate 作用下， 反应 1.0h， 生成 (Z)-3-(4-Fluoro-phenyl)-3-hydroxy-1-(2-hydroxy-4-phenethyloxy-phenyl)-propenone
  参考文献：
  名称：

  Synthesis of functionalized acetophenones as protein tyrosine phosphatase 1B inhibitors

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP1B knock-out mice showed increased insulin sensitivity in muscle and liver as well as resistance to obesity. A series of functionalized acetophenones were synthesized and evaluated for their PTP1B inhibitory activity. Some of the screened compounds displayed good inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.024
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 乙基溴苯 在 cesium bicarbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以89%的产率得到2-acetyl-5-(2-phenylethoxy)phenol
  参考文献：
  名称：

  2,4-二羟基苯甲醛和2,4-二羟基苯乙酮的区域选择性烷基化

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2022.153755

文献信息

• Aryloxyalkyloxy- and aralkyloxy-4-hydroxy-3-nitrocoumarins which inhibit histamine release in the rat and also antagonize the effects of a slow reacting substance of anaphylaxis
  作者：Derek R. Buckle、D. James Outred、Janet W. Ross、Harry Smith、Raymond J. Smith、Barbara A. Spicer、Brian C. Gasson

  DOI：10.1021/jm00188a007

  日期：1979.2

  The syntheses and structure--activity relationships of a number of 4-hydroxy-3-nitrocoumarins, which are both antagonists of a slow reacting substance of anaphylaxis and potent inhibitors of antigen-induced histamine release in the rat, are described. Most active among these are 7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy(-2-hydroxypropoxy] derivatives having hydrogen or lower alkyl substituents at the C-8 position of the coumarin ring, 168, 171, 173, and 174.
• 2-acetylphenol analogs as potent reversible monoamine oxidase inhibitors
  作者：Lesetja Legoabe、Jacobus Petzer、Anél Petzer

  DOI：10.2147/dddt.s86225

  日期：——

  Based on a previous report that substituted 2-acetylphenols may be promising leads for the design of novel monoamine oxidase (MAO) inhibitors, a series of C5-substituted 2-acetylphenol analogs (15) and related compounds (two) were synthesized and evaluated as inhibitors of human MAO-A and MAO-B. Generally, the study compounds exhibited inhibitory activities against both MAO-A and MAO-B, with selectivity for the B isoform. Among the compounds evaluated, seven compounds exhibited IC50 values <0.01 mu M for MAO-B inhibition, with the most selective compound being 17,000-fold selective for MAO-B over the MAO-A isoform. Analyses of the structure-activity relationships for MAO inhibition show that substitution on the C5 position of the 2-acetylphenol moiety is a requirement for MAO-B inhibition, and the benzyloxy substituent is particularly favorable in this regard. This study concludes that C5-substituted 2-acetylphenol analogs are potent and selective MAO-B inhibitors, appropriate for the design of therapies for neurodegenerative disorders such as Parkinson's disease.
• Synthesis of functionalized acetophenones as protein tyrosine phosphatase 1B inhibitors
  作者：Manish Dixit、Brajendra K. Tripathi、Arvind K. Srivastava、Atul Goel

  DOI：10.1016/j.bmcl.2005.05.024

  日期：2005.7

  Protein tyrosine phosphatase 1B (PTP1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP1B knock-out mice showed increased insulin sensitivity in muscle and liver as well as resistance to obesity. A series of functionalized acetophenones were synthesized and evaluated for their PTP1B inhibitory activity. Some of the screened compounds displayed good inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.
• 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。