2-acetyl-4-bromonaphthalen-1-yl trifluoromethanesulfonate | 1384513-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetyl-4-bromonaphthalen-1-yl trifluoromethanesulfonate
• CAS: 1384513-39-6
• 化学式: C₁₃H₈BrF₃O₄S
• 分子量: 397.169
• InChiKey: FCHBMDQFQRVXEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-4-bromonaphthalen-1-yl trifluoromethanesulfonate 、 4-氯苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以86%的产率得到2-acetyl-4-(4-chlorophenyl)naphthalen-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters

  摘要：

  Chemoselective Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the triflate group is electronically more deficient by the presence of a neighbouring acetyl group. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.026
• 作为产物：
  描述：

  三氟甲磺酸酐 、 4-溴-1-羟基-2-萘乙酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-acetyl-4-bromonaphthalen-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters

  摘要：

  Chemoselective Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the triflate group is electronically more deficient by the presence of a neighbouring acetyl group. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.026