2-(hydroxyimino)-1-(4-methoxyphenyl)-2-phenylethanone | 33420-68-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(hydroxyimino)-1-(4-methoxyphenyl)-2-phenylethanone
• 英文别名: 2-hydroxyimino-1-(4-methoxyphenyl)-2-phenylethanone
• CAS: 33420-68-7
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: SDDQJPHXDSRUQR-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  430.9±37.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(hydroxyimino)-1-(4-methoxyphenyl)-2-phenylethanone 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 ethyl 2-(6-(4-methoxyphenyl)-5-phenyl-1,2,4-triazine-3-ylthio)acetate
  参考文献：
  名称：

  Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity

  摘要：

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.

  DOI：

  10.1007/s00044-017-2003-x
• 作为产物：
  描述：

  1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 在 三氟甲磺酸 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 2-(hydroxyimino)-1-(4-methoxyphenyl)-2-phenylethanone
  参考文献：
  名称：

  α-酰基硝基甲烷的苯基化反应生成1,2-二酮一肟：α上的碳亲电体参与硝基

  摘要：

  研究了取代基的一般性及其对三氟甲磺酸催化的α-酰基硝基甲烷苯化反应的影响。α-芳酰基硝基甲烷以良好的收率提供了苯甲酰单肟。在脂族α-酰基硝基甲烷的情况下，进行了类似的苯基化反应，但是苯基化的1，2-二酮单肟的收率低。这些苯基化反应代表在硝基的α位上碳正离子亲电试剂的产生的实例。 α-酮硝基甲烷-1,2-二酮一肟-亲电子芳香取代-物质-质子化

  DOI：

  10.1055/s-0029-1217036

文献信息

• Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity
  作者：Tuba Tuylu Kucukkilinc、Kamaledin Safari Yanghagh、Beyza Ayazgok、Mohammad Ali Roknipour、Farshad Homayouni Moghadam、Alireza Moradi、Saeed Emami、Mohsen Amini、Hamid Irannejad

  DOI：10.1007/s00044-017-2003-x

  日期：2017.11

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.
• Phenylation Reaction of α-Acylnitromethanes To Give 1,2-Diketone Monooximes: Involvement of Carbon Electrophile at the Position α to the Nitro Group
  作者：Tomohiko Ohwada、Mikihiro Takamoto、Hiroaki Kurouchi、Yuko Otani

  DOI：10.1055/s-0029-1217036

  日期：——

  phe­nylation reactions of α-acylnitromethanes catalyzed by trifluoromethanesulfonic acid have been studied. α-Aroylnitromethanes afforded benzil monooximes in good yield. In the case of aliphatic α-acylnitromethane, a similar phenylation reaction proceeded, but the yield of the phenylated 1,2-dione monooxime was low. These phenylation reactions represent examples of the generation of carbocation electrophiles

  研究了取代基的一般性及其对三氟甲磺酸催化的α-酰基硝基甲烷苯化反应的影响。α-芳酰基硝基甲烷以良好的收率提供了苯甲酰单肟。在脂族α-酰基硝基甲烷的情况下，进行了类似的苯基化反应，但是苯基化的1，2-二酮单肟的收率低。这些苯基化反应代表在硝基的α位上碳正离子亲电试剂的产生的实例。 α-酮硝基甲烷-1,2-二酮一肟-亲电子芳香取代-物质-质子化