2'-(4-Fluorobenzyloxy)acetophenone | 400878-24-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(4-Fluorobenzyloxy)acetophenone
• 英文别名: 1-[2-[(4-fluorophenyl)methoxy]phenyl]ethanone
• CAS: 400878-24-2
• 化学式: C₁₅H₁₃FO₂
• mdl: MFCD03001269
• 分子量: 244.265
• InChiKey: GVLDMYWQSWDCMI-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2'-(4-Fluorobenzyloxy)acetophenone 、 在 sodium ethanolate 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Tetrazole and triazole as bioisosteres of carboxylic acid: Discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents

  摘要：

  A series of diketo tetrazoles and diketo triazoles were designed and synthesized as bioisosteres of alpha,gamma-diketo acid, the active site inhibitor of HCV (Hepatitis C virus) polymerase NS5B. Among the synthesized compounds, 4-(4-fluorobenzyloxy)phenyl diketo triazole (30) exhibited anti-HCV activity with an EC50 value of 3.9 mu M and an SI value more than 128. The reduction of viral protein and mRNA levels were also validated, supporting the anti-HCV activity of compound 30. These results provide convincing evidence that the diketo tetrazoles and diketo triazoles can be developed as bioisosteres of alpha,gamma-diketo acid to exhibit potent inhibitory activity against HCV. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.045
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 4-氟氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到2'-(4-Fluorobenzyloxy)acetophenone
  参考文献：
  名称：

  天然产物作为新型杀菌剂的来源（I）：苯乙酮衍生物对植物病原真菌的合成和抗真菌活性

  摘要：

  可以方便地合成几个带有各种烷基或苄基取代基的45种苯乙酮衍生物，并通过1 H和13 C NMR光谱，HRMS和单晶X射线分析对它们的结构进行表征。通过菌丝体生长速率测定法评估了它们对一组植物病原性真菌的体外抗真菌活性。在它们中，有12种衍生物（例如3a–c，4c和4e）对某些植物病原体表现出比作为阳性对照的商业杀菌剂氨甲唑更有效的抗真菌作用。特别是具有IC 50的化合物3b10–19μg/ mL的值被发现是该系列中最活跃的，可能是进一步优化的潜在先导结构。还讨论了一系列苯乙酮的初步结构-活性关系（SAR）研究。

  DOI：

  10.1111/cbdd.12064

文献信息

• Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi
  作者：Ya-Tuan Ma、Hua-Fang Fan、Yu-Qi Gao、He Li、An-Ling Zhang、Jin-Ming Gao

  DOI：10.1111/cbdd.12064

  日期：2013.4

  Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single‐crystal X‐ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a–c, 4c and 4e) exhibited

  可以方便地合成几个带有各种烷基或苄基取代基的45种苯乙酮衍生物，并通过1 H和13 C NMR光谱，HRMS和单晶X射线分析对它们的结构进行表征。通过菌丝体生长速率测定法评估了它们对一组植物病原性真菌的体外抗真菌活性。在它们中，有12种衍生物（例如3a–c，4c和4e）对某些植物病原体表现出比作为阳性对照的商业杀菌剂氨甲唑更有效的抗真菌作用。特别是具有IC 50的化合物3b10–19μg/ mL的值被发现是该系列中最活跃的，可能是进一步优化的潜在先导结构。还讨论了一系列苯乙酮的初步结构-活性关系（SAR）研究。
• Tetrazole and triazole as bioisosteres of carboxylic acid: Discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents
  作者：Wu-Hui Song、Ming-Ming Liu、Dong-Wei Zhong、Ye-lin Zhu、Mike Bosscher、Lu Zhou、De-Yong Ye、Zheng-Hong Yuan

  DOI：10.1016/j.bmcl.2013.06.045

  日期：2013.8

  A series of diketo tetrazoles and diketo triazoles were designed and synthesized as bioisosteres of alpha,gamma-diketo acid, the active site inhibitor of HCV (Hepatitis C virus) polymerase NS5B. Among the synthesized compounds, 4-(4-fluorobenzyloxy)phenyl diketo triazole (30) exhibited anti-HCV activity with an EC50 value of 3.9 mu M and an SI value more than 128. The reduction of viral protein and mRNA levels were also validated, supporting the anti-HCV activity of compound 30. These results provide convincing evidence that the diketo tetrazoles and diketo triazoles can be developed as bioisosteres of alpha,gamma-diketo acid to exhibit potent inhibitory activity against HCV. (c) 2013 Elsevier Ltd. All rights reserved.