2-hydroxyamino-1-phenylpropanone oxime | 5111-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxyamino-1-phenylpropanone oxime
• 英文别名: N-<1-anti-Hydroxyimino-1-phenylpropyl-(2)>-hydroxylamin；N-(1-anti-Oximino-1-phenylpropyl-2)hydroxylamine；N-(1-anti-Hydroxyimino-1-phenylpropyl-(2))-hydroxylamin
• CAS: 5111-30-8
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: WTLQALTZHQWCJK-LUAWRHEFSA-N

物化性质

• 沸点：
  361.1±44.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.85
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyamino-1-phenylpropanone oxime 在 sodium tetrahydroborate 、 乙醇 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1-hydroxy-2-(α-hydroxybenzyl)-4-methyl-5-phenyl-1Н-imidazole
  参考文献：
  名称：

  Synthesis of 2-Aroyl(Hetaroyl)-1-Hydroxy- Imidazoles by the Interaction of Alkyl-Aromatic α-Hydroxyaminooximes with Aryl(Hetaryl)Glyoxals

  摘要：

  The interaction of alkylaromatic and alkylheteroaromatic alpha-hydroxyaminooximes with aryl(hetaryl)-glyoxals hydrates produced a new series of 2-aroyl(hetaroyl)-5-aryl(hetaryl)-1-hydroxy-4-methylimid-azoles. The X-ray structural data for 2-benzoyl-5-(4-fluorophenyl)-1-hydroxy-4-methylimidazole are presented.

  DOI：

  10.1007/s10593-014-1523-2

文献信息

• Synthesis of 2-aryl(hetaryl)-1-hydroxyimidazoles by the reaction of aliphatic 1,2-hydroxylamino oximes with aromatic and heteroaromatic aldehydes
  作者：B. A. Selivanov、A. Ya. Tikhonov

  DOI：10.1007/s11172-013-0169-z

  日期：2013.5

  A reaction of aliphatic 1,2-hydroxylamino oximes bearing the hydroxylamino group at the secondary carbon atom with aromatic and heteroaromatic aldehydes in acetic acid leads to the corresponding 1-hydroxy-2-aryl(hetaryl)-4,5-dialkylimidazoles in high yields. α-Aryl(hetaryl)-nitrones initially formed by the condensation of 1,2-hydroxylamino oximes with aldehydes are quantitatively converted to the corresponding imidazoles.

  脂肪族1,2-羟基氨基肟在乙酸中与芳香族和杂芳族醛反应，在仲碳原子上带有羟基氨基，从而高产量地生成相应的1-羟基-2-芳基（杂芳基）-4,5-二烷基咪唑。α-芳基（杂芳基）-腈酮最初由1,2-羟基氨基肟与醛缩合形成，然后定量转化为相应的咪唑。
• Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate
  作者：Elena B. Nikolaenkova、Alexei Ya. Tikhonov、Stanislav Yu. Grishchenko

  DOI：10.1007/s10593-019-02430-8

  日期：2019.2

  α-hydroxyamino oximes with the anti configuration of the oxime group reacted with ethyl glyoxylate to form 5-aryl(hetaryl)-1-hydroxy-1H-imidazole-2-carboxylic acid ethyl esters. In the case of 4-fluorophenyl-, 4-chlorophenyl-, and 4-methoxyphenyl-substituted α-hydroxyamino oximes, 3-aryl-5-hydroxy-5,6-dihydro-4H-1,2,5-oxadiazine-6-carboxylic acid ethyl esters were also formed. The positions of the substituents

  具有肟基的反式构型的烷基（杂）芳族α-羟基氨基肟与乙醛酸乙酯反应生成5-芳基（杂芳基）-1-羟基-1 H-咪唑-2-羧酸乙酯。在被4-氟苯基，4-氯苯基和4-甲氧基苯基取代的α-羟基氨基肟的情况下，3-芳基-5-羟基-5,6-二氢-4 H -1,2,5-恶二嗪-还形成了6-羧酸乙酯。在对这些产物和合成的异构化合物1-羟基-5-甲基-4-苯基-1H-咪唑-2-的光谱数据进行比较分析的基础上，确定了咪唑环中取代基的位置。羧酸乙酯。5-芳基（杂芳基）-1 H在5-芳基（杂芳基）-1-羟基-1 H-咪唑-2-羧酸乙酯与氯丙酮反应中获得-咪唑-2-羧酸。
• Synthesis of 2-[2-(hydroxyimino)alkyl]-1,2-oxazol-5(2Н)-ones
  作者：Elena B. Nikolaenkova、Irina Yu. Bagryanskaya、Alexsei Ya. Tikhonov

  DOI：10.1007/s10593-020-02645-0

  日期：2020.2

  The reaction of α-hydroxyamino oximes with ethyl acetoacetate and ethyl α-methylacetoacetate yields 2-[2-(hydroxyimino)alkyl]-1,2-oxazol-5(2H)-ones. In the reaction of alkylaromatic α-hydroxyamino oximes with ethyl acetoacetate, the intermediate imidazo[1,2-b]-[1,2]oxazolones were isolated, which then convert to the target compounds.

  α-羟氨基肟与乙酰乙酸乙酯和α-甲基乙酰乙酸乙酯的反应产生2- [2-（羟基亚氨基）烷基] -1，2-恶唑-5（2H）-1。在烷基芳族α-羟基氨基肟与乙酰乙酸乙酯的反应中，分离出中间体咪唑并[1,2- b ]-[1,2]恶唑酮，然后转化为目标化合物。