2-(2-溴苯基)-1-(4-氟苯基)丙烷-1-酮 | 823787-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(2-溴苯基)-1-(4-氟苯基)丙烷-1-酮
• 英文名称: 2-(2-bromophenyl)-1-(4-fluorophenyl)propan-1-one
• 英文别名: 2-(2-Bromophenyl)-1-(4-fluorophenyl)propan-1-one
• CAS: 823787-26-4
• 化学式: C₁₅H₁₂BrFO
• 分子量: 307.162
• InChiKey: AWYSIECVUSEXNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-(2-溴苯基)-1-(4-氟苯基)丙烷-1-酮 在 tris(dibenzylideneacetone)dipalladium (0) 、 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以68%的产率得到2-(4-fluorophenyl)-3-methylbenzofuran
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular O-Arylation of Enolates:  Application to Benzo[b]furan Synthesis

  摘要：

  A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects intramolecular C-O bond formation between enolates and aryl halides in the conversion of 1-(2-haloaryl)ketones directly into the corresponding benzofurans. Both cyclic and acyclic ketones are efficient substrates. Thio ketones can also be employed allowing the preparation of the corresponding benzothiophenes.

  DOI：

  10.1021/ol047993g
• 作为产物：
  描述：

  4'-氟苯丙酮 、 邻碘溴苯 在 tris(dibenzylideneacetone)dipalladium (0) base 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(2-溴苯基)-1-(4-氟苯基)丙烷-1-酮
  参考文献：
  名称：

  Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes

  摘要：

  Enolates derived from alpha-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required a-aryl ketones in situ has also been developed, although the substrate scope is more restricted. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.004

文献信息

• Palladium-catalyzed aryl halide carbonylation–intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A
  作者：Andrew C. Tadd、Mark R. Fielding、Michael C. Willis

  DOI：10.1039/b917839b

  日期：——

  Exposure of a series of α-(o-haloaryl)-substituted ketones to palladium-catalyzed carbonylation conditions leads to the formation of the corresponding isocoumarins. Balloon pressure of CO is sufficient to achieve high yielding reactions, and both cyclic and acyclic ketones are efficient substrates. The utility of the method is illustrated by a short synthesis of the natural product thunberginol A.

  一系列α-(o-卤芳基)-取代酮在钯催化的羰基化条件下处理，导致相应异香豆素的形成。使用气球压力的CO即可实现高产率反应，且环状和非环状酮都是高效底物。这种方法的实用性通过简短合成天然产物thunberginol A得到了说明。
• Palladium-Catalyzed Tandem Alkenyl and Aryl C?N Bond Formation: A Cascade N-Annulation Route to 1-Functionalized Indoles
  作者：Michael C. Willis、Gareth N. Brace、Ian P. Holmes

  DOI：10.1002/anie.200461598

  日期：2005.1.7
• Palladium-Catalyzed Intramolecular <i>O</i>-Arylation of Enolates:  Application to Benzo[<i>b</i>]furan Synthesis
  作者：Michael C. Willis、Dawn Taylor、Adam T. Gillmore

  DOI：10.1021/ol047993g

  日期：2004.12.1

  A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects intramolecular C-O bond formation between enolates and aryl halides in the conversion of 1-(2-haloaryl)ketones directly into the corresponding benzofurans. Both cyclic and acyclic ketones are efficient substrates. Thio ketones can also be employed allowing the preparation of the corresponding benzothiophenes.
• Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes
  作者：Michael C. Willis、Dawn Taylor、Adam T. Gillmore

  DOI：10.1016/j.tet.2006.05.004

  日期：2006.12

  Enolates derived from alpha-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required a-aryl ketones in situ has also been developed, although the substrate scope is more restricted. (c) 2006 Elsevier Ltd. All rights reserved.