5'-Acetoxy-2'-hydroxyacetophenone | 21222-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-Acetoxy-2'-hydroxyacetophenone
• 英文别名: 3-acetyl-4-hydroxyphenyl acetate；5-acetoxy-2-hydroxyacetophenone；quinacetophenone-5-acetate；4-acetoxy-2-acetylphenol；1-(5-acetoxy-2-hydroxy-phenyl)-ethanone；1-(5-Acetoxy-2-hydroxy-phenyl)-aethanon；(3-acetyl-4-hydroxyphenyl) acetate
• CAS: 21222-04-8
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD02114695
• 分子量: 194.187
• InChiKey: MMOTWJGMUVIYAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  91°C
• 沸点：
  327.2±32.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-Acetoxy-2'-hydroxyacetophenone 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 6-羟基-4-氧代-4H-色烯-3-甲醛
  参考文献：
  名称：

  Inhibition of Alzheimer’s BACE-1 by 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates

  摘要：

  Alzheimer's disease is the most common cause of dementia in the elderly, and no disease-modifying therapy is yet available for this devastating pathology. Deposition of different physicochemical forms of amyloid-beta peptides is a critical phase in the pathogenesis of Alzheimer's disease. beta-Site amyloid precursor protein cleaving enzyme 1 (BACE-1) is a major enzyme responsible for amyloid-beta production; therefore, inhibition of this enzyme represents a promising approach for the discovery of amyloid-beta-lowering agents. In this study, a series of novel 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates (14-23) were synthesized and assessed as BACE-1 inhibitors using the Forster resonance energy transfer-based enzyme assay. Synthesized dihydropyridines exhibited weak-to-relatively-good BACE-1 inhibitory activities. Enzyme inhibitory activities ranged from 6.84 +/- A 6.62 (23) to 51.32 +/- A 1.04 (14) percent enzyme inhibitions at the concentration of 10 mu M. The structure-activity relationship study showed that the presence of 4-[7-(ethanoyloxy)-4-oxo-4H-chromen-3-yl] moiety at C4 position of dihydropyridine ring (14, 16 and 18) confers higher activity compared with other substitutions at this position. Docking simulation predicted a key H-bond interaction between Asp32 residue and dihydropyridine NH group. Moreover, all docked dihydropyridines made good hydrophobic contacts with S1 and S2 subpockets of BACE-1. A good correlation between estimated binding affinities (pK(i)) and experimental BACE-1 inhibitory activities at 10 mu M was obtained (R (2) = 0.639). The findings of this study suggested that 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates could be promising scaffolds for the discovery of novel BACE-1 inhibitors for management of Alzheimer's disease.

  DOI：

  10.1007/s00044-015-1367-z
• 作为产物：
  描述：

  对二乙酰氧基苯 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 以12%的产率得到5'-Acetoxy-2'-hydroxyacetophenone
  参考文献：
  名称：

  三氟甲磺酸铋催化的 Fries 重排乙酸芳酯

  摘要：

  发现三氟甲磺酸铋是苯基或 1-萘基乙酸酯的 Fries 重排的有效催化剂。在大多数情况下，使用催化量的三氟甲磺酸铋（10 mol%），两个反应都能顺利进行，以中等至良好的产率得到相应的羟基芳基酮。

  DOI：

  10.1055/s-2004-836025

文献信息

• Application of E1cB Elimination in Asymmetric Organocatalytic Cascade Reactions To Construct Polyheterocyclic Compounds
  作者：Zhi-Hao You、Ying-Han Chen、Yu Tang、Yan-Kai Liu

  DOI：10.1021/acs.orglett.9b03138

  日期：2019.10.18

  By introducing a carbon functionality at 2-position of chromane, the formal asymmetric functionalization of the 3-position of 2-substituted chromane has been realized via a highly chemo-, regio-, and stereoselective organocatalytic cascade reaction in a sequential one-pot manner involving an E1cB mechanism governed ring-opening process. Critical to our success was the design of a chiral dipeptide-based

  通过在色烷的2位上引入碳官能团，已通过高化学，区域和立体选择性有机催化级联反应以顺序一锅方式实现了2位取代的色烷3位的形式不对称官能化涉及E1cB机制控制的开环过程。我们成功的关键是设计基于手性二肽的双官能酸基有机催化剂，该催化剂在低催化剂负载量（1-0.1 mol％）下表现出高催化活性，从而导致了生物学上令人感兴趣的多杂环化合物。
• Synthesis and evaluation of c-Src kinase inhibitory activity of pyridin-2(1H)-one derivatives
  作者：Karam Chand、Suchita Prasad、Rakesh K. Tiwari、Amir N. Shirazi、Sumit Kumar、Keykavous Parang、Sunil K. Sharma

  DOI：10.1016/j.bioorg.2014.02.001

  日期：2014.4

  Src kinase, a prototype member of the Src family of kinases (SFKs), is over-expressed in various human tumors, and has become a target for anticancer drug design. In this perspective, a series of eighteen 2-pyridone derivatives were synthesized and evaluated for their c-Src kinase inhibitory activity. Among them, eight compounds exhibited c-Src kinase inhibitory activity with IC50 value of less than

  Src激酶是Src激酶家族（SFKs）的原型成员，在各种人类肿瘤中均过表达，已成为抗癌药物设计的目标。从这个角度出发，合成了一系列十八个2-吡啶酮衍生物，并评估了它们的c-Src激酶抑制活性。其中，八种化合物表现出c-Src激酶抑制活性，IC 50值小于25μM。化合物1- [2-（二甲基氨基）乙基] -5-（2-羟基-4-甲氧基苯甲酰基）吡啶-2（1H）-一（36）表现出最高的c-Src激酶抑制作用，IC 50值为12.5μM 。此外，化合物36的激酶抑制活性研究人员针对EGFR，MAPK和PDK进行了研究，但在最高测试浓度（300μM）下未观察到明显的活性。这些结果为进一步优化该支架以设计下一代2-吡啶酮衍生物作为候选Src激酶抑制剂提供了见识。
• Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes
  作者：Jessica L. Boyer、Jodie E. Krum、Michael C. Myers、Aleem N. Fazal、Carl T. Wigal

  DOI：10.1021/jo000412q

  日期：2000.7.1

  trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.

  三氟化硼甲基和乙基醚化物配合物与对苯二酚二酯的反应可生成乙酰氢醌的单甲基和单乙基衍生物。使用位阻三氟化硼醚化物配合物会生成乙酰氢醌衍生物。该步骤代表一步合成乙酰氢醌衍生物，这是各种合成应用的重要组成部分。
• Lipase-catalyzed regioselective protection of hydroxyl groups in aromatic dihydroxyaldehydes and ketones
  作者：Giovanni Nicolisi、Mario Piattelli、Claudia Sanfilippo

  DOI：10.1016/s0040-4020(01)89897-5

  日期：1993.4

  Pseudomonas cepacia lipase catalyzes the acetylation in organic solvent of dihydroxyaldehydes and ketones using vinyl acetate as acyl donor. The method is completely regioselective and allows to obtain partially acetylated compounds different from those obtained by enzymic hydrolysis of polyacetoxy arylaldehydes and ketones.

  假单胞菌洋葱脂肪酶在乙酸乙烯酯作为酰基供体的情况下催化二羟基醛和酮在有机溶剂中的乙酰化。该方法是完全区域选择性的，并允许获得部分乙酰化的化合物，该化合物与通过酶水解聚乙酰氧基芳基醛和酮获得的化合物不同。
• Synthesis,¹H and¹³C NMR assignment of novel 2-pyridone derivatives
  作者：Karam Chand、Atul K. Sharma、Sunil K. Sharma

  DOI：10.1002/mrc.4321

  日期：2016.1

  pigments. Because the substitution of various functional groups on pyridin-2(1H)-one nucleus greatly affects the chemical shift values in the magnetic resonance of the proton and carbon nucleus, herein, we have synthesized a series of N-substituted derivatives of benzoylpyridin2-(1H)-ones and studied the impact of the different substituents on the chemical shifts of the protons and carbons of pyridone

  由于其在药物化学中的重要性，2-吡啶酮核心结构的合成是合成有机化学家的一个有吸引力的目标。此外，2-吡啶酮构成了几种天然先导化合物的结构成分，例如石杉碱甲、弗雷德里霉素 A、喜树碱 (CTP)、伊利西林 H 和吡哆醇。许多含有吡啶酮骨架的药物已经进入临床世界，还有一些正在临床试验中，例如氨力农、米力农或普立马可作为强心剂用于治疗心力衰竭，吡仑帕奈用于治疗帕金森病，吡非尼酮用于治疗特发性肺纤维化，环吡唑胺用于皮肤感染的局部治疗。2-吡啶酮的潜在临床适用性和相对较低的毒性引起了许多研究人员的兴趣，以探索该部分对更好和多样化药理活性的效用。除了药用特性外，2-吡啶酮衍生物还可以作为吡啶、哌啶、喹唑啉和吲哚里西啶生物碱的活性合成子以及用于染料和颜料的吡啶酮系链系统。由于吡啶-2(1H)-one核上各种官能团的取代极大地影响了质子核和碳核磁共振中的化学位移值，在此，我们合成了一系列苯甲酰基吡啶2-(