2-phenoxy-1-phenylethan-1-one oxime | 187672-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-phenoxy-1-phenylethan-1-one oxime
• 英文别名: 2-Phenoxy-1-phenyl-ethanone oxime；(NZ)-N-(2-phenoxy-1-phenylethylidene)hydroxylamine
• CAS: 187672-26-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: SVEDYNQHOMCDBL-CCEZHUSRSA-N

物化性质

• 沸点：
  396.9±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2’-苯氧基苯乙酮 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以52%的产率得到2-phenoxy-1-phenylethan-1-one oxime
  参考文献：
  名称：

  Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones

  摘要：

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.

  DOI：

  10.1111/j.1747-0285.2012.01432.x

文献信息

• Transformation of lignin model compounds to<i>N</i>-substituted aromatics<i>via</i>Beckmann rearrangement
  作者：Yinling Wang、Yiman Du、Jianghua He、Yuetao Zhang

  DOI：10.1039/c8gc00920a

  日期：——

  Here we present the highly effective cleavage of C–C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate

  这里，我们提出的C-C键的高度有效的裂解在木质素模型化合物用于生产ñ -取代的芳族化合物在高达96％的总收率，包括苄腈和酰胺，经由肟形成随后贝克曼重排（BR）。酰胺可以分别进一步水解为苯胺（产率> 92％）和羧酸（> 90％）。另外，使用具有γ-OH基团的底物将导致形成C -2单取代的恶唑。还开发了一种涉及BR反应和水解的一锅法，可直接提供高达96％的苯甲腈，苯甲酰胺和苯胺总产率。这种策略使我们能够成功地将BR反应应用于木质素模型化合物的降解在温和条件下经过N-官能化的芳族产品。
• Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones
  作者：Mahsa Ansari、Saeed Emami、Mohammad A. Khalilzadeh、Malek T. Maghsoodlou、Alireza Foroumadi、Mohammad A. Faramarzi、Nasrin Samadi、Sussan K. Ardestani

  DOI：10.1111/j.1747-0285.2012.01432.x

  日期：2012.10

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.