2-oxo-1,2-diphenylethyl 2-fluorobenzoate | 482295-82-9

• 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-oxo-1,2-diphenylethyl 2-fluorobenzoate
• 英文别名: (2-Oxo-1,2-diphenylethyl) 2-fluorobenzoate
• CAS: 482295-82-9
• 化学式: C₂₁H₁₅FO₃
• 分子量: 334.347
• InChiKey: QXODJKDIYOZQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-diphenylethyl 2-fluorobenzoate 在 ammonium acetate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-(4'-Methoxy-biphenyl-2-yl)-4,5-diphenyl-oxazole
  参考文献：
  名称：

  恶唑是掩蔽的羧基，可激活亲核芳香取代中的邻位离去基团

  摘要：

  在其 2-位被 2-甲氧基-、2-氟-或 2,6-二氟苯基取代，并在其 4,5-位被甲基或苯基取代的恶唑，用 ArMgBr 或 ArLi 处理得到取代的联苯或三联苯产品。恶唑基团随后转化为酯、酸或酰胺。这些反应提供了一种新的不对称芳基-芳基偶联合成子。

  DOI：

  10.1246/cl.1987.19
• 作为产物：
  描述：

  安息香精油 、 邻氟苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到2-oxo-1,2-diphenylethyl 2-fluorobenzoate
  参考文献：
  名称：

  Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

  摘要：

  The oncogenic potential of phosphatidylinositol 3-kinase (PI3K alpha) has made it an attractive target for anticancer drug design. In this work, we describe our efforts to optimize the lead PI3K alpha inhibitor 2-hydroxy-1,2-diphenylethanone (benzoin). A series of 2-oxo-1,2-diphenylethyl benzoate analogs were identified as potential PI3K alpha inhibitors. Docking studies confirmed that the aromatic interaction is mediating ligand/protein complex formation and identified Lys802 and Val851 as H-bonding key residues. Our biological data in human colon carcinoma HCT116 showed that the structure analogs inhibited cell proliferation and induced apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.011

文献信息

• Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)
  作者：Dima A. Sabbah、Musaab Saada、Reema Abu Khalaf、Sanaa Bardaweel、Kamal Sweidan、Tariq Al-Qirim、Amani Al-Zughier、Heba Abdel Halim、Ghassan Abu Sheikha

  DOI：10.1016/j.bmcl.2015.06.011

  日期：2015.8

  The oncogenic potential of phosphatidylinositol 3-kinase (PI3K alpha) has made it an attractive target for anticancer drug design. In this work, we describe our efforts to optimize the lead PI3K alpha inhibitor 2-hydroxy-1,2-diphenylethanone (benzoin). A series of 2-oxo-1,2-diphenylethyl benzoate analogs were identified as potential PI3K alpha inhibitors. Docking studies confirmed that the aromatic interaction is mediating ligand/protein complex formation and identified Lys802 and Val851 as H-bonding key residues. Our biological data in human colon carcinoma HCT116 showed that the structure analogs inhibited cell proliferation and induced apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.
• Oxazoles Are Masked Carboxyls That Activate Ortho-Leaving Groups in Nucleophilic Aromatic Substitution
  作者：Donald J. Cram、Judi A. Bryant、Kenneth M. Doxsee

  DOI：10.1246/cl.1987.19

  日期：1987.1.5

  Oxazoles substituted in their 2-positions with 2-methoxy-, 2-fluoro-, or 2,6-difluorophenyl groups, and in their 4,5-positions with methyls or phenyls, were treated with ArMgBr or ArLi to give substituted biphenyl or terphenyl products. The oxazole groups were subsequently converted to esters, acids, or amides. These reactions provide a new unsymmetrical aryl-aryl coupling synthon.

  在其 2-位被 2-甲氧基-、2-氟-或 2,6-二氟苯基取代，并在其 4,5-位被甲基或苯基取代的恶唑，用 ArMgBr 或 ArLi 处理得到取代的联苯或三联苯产品。恶唑基团随后转化为酯、酸或酰胺。这些反应提供了一种新的不对称芳基-芳基偶联合成子。