2'-hexanoyloxyacetophenone | 957273-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-hexanoyloxyacetophenone
• 英文别名: 2-acetylphenyl hexanoate
• CAS: 957273-14-2
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: QZMDKLVAJXULEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2'-hexanoyloxyacetophenone 在 potassium tert-butylate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 2-(5-pentyl-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  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.

  DOI：

  10.1021/acschembio.5b00934
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 己酰氯 在 吡啶 作用下， 反应 2.0h， 以49%的产率得到2'-hexanoyloxyacetophenone
  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

文献信息

• Cu(II)-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level
  作者：Satyasheel Sharma、Jihye Park、Mirim Kim、Jong Hwan Kwak、Young Hoon Jung、In Su Kim

  DOI：10.1016/j.tet.2013.08.079

  日期：2013.11

  A copper-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level is described. This protocol represents direct access to a range of 2-carbonylated aryl benzoate derivatives, which are important building blocks in the synthesis of natural and pharmacological compounds. (C) 2013 Elsevier Ltd. All rights reserved.