2'-(2,2-dimethylpropanoyloxy)acetophenone | 135276-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(2,2-dimethylpropanoyloxy)acetophenone
• 英文别名: (2-Acetylphenyl) 2,2-dimethylpropanoate
• CAS: 135276-49-2
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: UVOQGPIORCCHPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-(2,2-dimethylpropanoyloxy)acetophenone 在 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到2'-(2,2-dimethylpropanoyloxy)-2-bromoacetophenone
  参考文献：
  名称：

  Structure–activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2

  摘要：

  Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study has been restricted to those compounds found in nature, which have limited structural variability. We have therefore carried out a comprehensive study to determine the structural requirements for flavonoid potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. We conclude from this study that catechols are essential for high potency, that isoflavones and isoflavanones tend to select against 12-hLO, that isoflavans tend to select against 15-hLO-1, but few flavonoids target 15-hLO-2. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.036
• 作为产物：
  描述：

  三甲基乙酰氯 、 2'-羟基苯乙酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到2'-(2,2-dimethylpropanoyloxy)acetophenone
  参考文献：
  名称：

  Synthesis of Five-, Six-, and Seven-Membered Heterocycles by Intramolecular Ring Opening Reactions of 3-Oxetanol Derivatives

  摘要：

  Intramolecular ring opening reactions of 2-phenyl-3-oxetanols have been studied. The starting materials were prepared by the photocycloaddition of benzaldehyde and various silyl enol ethers. The intramolecular nucleophile was either incorporated into the silyl enol ether prior to the Paterno-Buchi reaction (oxetanes 3, 16) or was later installed by functional group interconversion (oxetanes 5. 12). With anionic heteroatom nucleophiles (O, N, S) which were attached to the carbon atom C-3 of the trimethylsilyl-protected oxetanol via an alkyl chain, a substitution at the less substituted position C-4 was observed and the corresponding heterocycles (6, 8, 13, 19) were obtained in moderate to good yields (52-91%). Upon acid catalysis a ring opening of the Boc-protected 3-oxetanol 23 to cyclic carbonates occurred. The reaction did not proceed stereospecifically and resulted in a mixture of diastereomeric products 24 and 25.

  DOI：

  10.1021/jo971866z

文献信息

• Intramolecular Nucleophilic Substitution at the C-4 Position of Functionalized Oxetanes:  A Ring Expansion for the Construction of Various Heterocycles
  作者：Thorsten Bach、Kristian Kather

  DOI：10.1021/jo961436t

  日期：1996.1.1
• Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in <i>Staphylococcus aureus</i>
  作者：Brendan F. Dutter、Laura A. Mike、Paul R. Reid、Katherine M. Chong、Susan J. Ramos-Hunter、Eric P. Skaar、Gary A. Sulikowski

  DOI：10.1021/acschembio.5b00934

  日期：2016.5.20

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.