acetophenone O-methyloxime | 1148107-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetophenone O-methyloxime
• 英文别名: 3-oxo-3-phenylpropanal oxime methyl ether；3-methoxyimino-1-phenylpropan-1-one
• CAS: 1148107-61-2
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: YTSAVGNYVXXFKR-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  287.1±42.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Benzoylacetaldoxim 、 碘甲烷 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以68%的产率得到acetophenone O-methyloxime
  参考文献：
  名称：

  An effective Biginelli-type synthesis of 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones

  摘要：

  The ternary condensation of N-methoxyurea, aldehydes, and 1,3-dicarbonyl compounds, resulting in novel 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones has been examined. Commonly used reaction conditions and catalysts (EtOH/HCl, HOAc, DMF) proved to be unsuitable and we found that the DMF-TMSCl system was the best catalyst. Similarly, the reaction of ureas with 4-chlorobenzaldehyde and 1;3-cyclohexanedione using the DMF/TMSCl system afforded 3,4,7,8-tetrahydroquinazolin-2,5(1H,6H)-diones, while other catalyst systems resulted in the formation of product mixtures. In addition, we have developed an effective and simple protocol for the synthesis of N-(methoxy)urea. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.041

文献信息

• Synthesis and antibacterial evaluation of novel 4-alkyl substituted phenyl β-aldehyde ketone derivatives
  作者：Jinbing Liu、Rihui Cao、Qifeng Wu、Chunming Ma、Zihou Wang、Wenlie Peng、Huacan Song

  DOI：10.1016/j.ejmech.2008.03.010

  日期：2009.4

  A series of novel 4-alkylphenyl β-aldehyde ketones and their derivatives were designed and synthesized on the basis of the chemical structures of Houttuynin and β-lactam antibiotics. Antibacterial activities of these compounds were investigated. The results demonstrated that most of the compounds tested had moderate antibacterial activities against Gram-positive pathogen Staphylococcus aureus (ATTC-25923)

  根据鱼腥草素和β-内酰胺类抗生素的化学结构，设计合成了一系列新型的4-烷基苯基β-醛酮及其衍生物。研究了这些化合物的抗菌活性。结果表明，所测试的大多数化合物对革兰氏阳性病原体金黄色葡萄球菌（ATTC-25923）的抑制作用均比Houttuynin大，而革兰氏阳性菌比革兰氏阴性菌更容易受到该化合物的影响。发现化合物23是最有效的化合物，对金黄色葡萄球菌的MIC为1.0μg/ mL 。特别是，化合物16，22和23在临床上重要的病原细菌，耐甲氧西林的金黄色葡萄球菌（MRSA）表现出比Houttuynin和左氧氟沙星更强的抗菌活性。初步的结构-活性关系（SAR）分析表明：（1）在苯环的4位引入合适的烷基取代基可增强这些化合物的抗菌活性，而异丙基取代基可能更有利；（2）酮羰基部分的存在可能在确定这些化合物的显着抗菌活性中起着至关重要的作用。