2-(2-bromo-5-fluorophenyl)-3,4-dihydro-2H-naphthalan-1-one | 823787-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-bromo-5-fluorophenyl)-3,4-dihydro-2H-naphthalan-1-one
• 英文别名: 2-(2-Bromo-5-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one；2-(2-bromo-5-fluorophenyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 823787-28-6
• 化学式: C₁₆H₁₂BrFO
• 分子量: 319.173
• InChiKey: YCWXMSLLYYOEJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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-bromo-5-fluorophenyl)-3,4-dihydro-2H-naphthalan-1-one 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 48.0h， 以74%的产率得到8-fluoro-5,6-dihydrobenzo[β]naphtho[2,1-δ]furan
  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：

  3,4-二氢-1(2H)-萘酮 、 2-碘-4-氟溴苯 在 tris(dibenzylideneacetone)dipalladium (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以57%的产率得到2-(2-bromo-5-fluorophenyl)-3,4-dihydro-2H-naphthalan-1-one
  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

文献信息

• 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.