2-bromo-3-(4-fluorophenyl)-1H-inden-1-one | 1092564-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-bromo-3-(4-fluorophenyl)-1H-inden-1-one
• 英文别名: 2-Bromo-3-(4-fluorophenyl)inden-1-one
• CAS: 1092564-92-5
• 化学式: C₁₅H₈BrFO
• 分子量: 303.13
• InChiKey: WOQRDBXPIARWMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(4-fluorophenyl)-1H-inden-1-one 、 吡啶-4-硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 以12%的产率得到2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-inden-1-one
  参考文献：
  名称：

  Phenylindenone isomers as divergent modulators of p38α MAP kinase

  摘要：

  Two new fluorophenylindenone derivatives were designed as potential p38 alpha, MAPK modulators by preserving the key interactions of the vicinal pyridine/fluorophenyl pharmacophore with the enzyme protein. Interestingly, these two fluorophenylindenone isomers showed divergent activities, with compound 6 behaving as an inhibitor and 5 as a putative activator. These results were rationalized by docking studies and molecular dynamics simulations in terms of stabilization of DFG loop, by compound 5 in a conformation more accessible to phosphorylation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.001
• 作为产物：
  描述：

  3-(4-fluorophenyl)-2-(trimethylsilyl)-1H-inden-1-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到2-bromo-3-(4-fluorophenyl)-1H-inden-1-one
  参考文献：
  名称：

  Phenylindenone isomers as divergent modulators of p38α MAP kinase

  摘要：

  Two new fluorophenylindenone derivatives were designed as potential p38 alpha, MAPK modulators by preserving the key interactions of the vicinal pyridine/fluorophenyl pharmacophore with the enzyme protein. Interestingly, these two fluorophenylindenone isomers showed divergent activities, with compound 6 behaving as an inhibitor and 5 as a putative activator. These results were rationalized by docking studies and molecular dynamics simulations in terms of stabilization of DFG loop, by compound 5 in a conformation more accessible to phosphorylation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.001

文献信息

• Facile Synthesis of Alkyl 1-Oxo-3-phenyl-1<i>H</i>-indene-2-carboxylate through Palladium-catalyzed Carboalkoxylation from 2-Bromo-3-phenylinden-1-ones
  作者：Eul Kgun Yum、Woul Seong Park、Se Hoan Kim、Seung Kyu Kang、Sung Soo Kim、Jin Hee Ahn

  DOI：10.1246/cl.2008.1068

  日期：2008.10.5

  Palladium-catalyzed carboalkoxylation of 2-bromo-3-phenylindenones in various alcoholic solvents afforded diverse alkyl 1-oxo-3-phenyl-1H-indene-2-carboxylates in high yields.

  钯催化的 2-溴-3-苯基茚酮在各种醇溶剂中的碳烷氧基化以高产率提供了多种 1-氧代-3-苯基-1H-茚-2-羧酸烷基酯。
• Site-selective Suzuki–Miyaura reactions of 2,3-dibromo-1H-inden-1-one
  作者：Munawar Hussain、Nguyen Thai Hung、Rasheed Ahmed Khera、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tetlet.2010.10.101

  日期：2011.1

  The first transition metal-catalyzed cross-coupling reactions of 2,3-dibromo-1H-inden-1-one are reported. The Suzuki-Miyaura reaction of 2,3-dibromo-1H-inden-1-one with 2 equiv of arylboronic acid gave 2,3-diaryl-1H-inden-1-ones. The reaction with 1 equiv of arylboronic acid gave 2-bromo-3-aryl-1H-inden-1-ones with very good site-selectivity. The one-pot reaction of 2,3-dibromo-1H-inden-1-one with two different arylboronic acids afforded 2,3-diaryl-1H-inden-1-ones containing two different terminal aryl groups. (C) 2010 Elsevier Ltd. All rights reserved.