potassium [4-(cyclohexyl(hydroxyl)methyl)phenyl]trifluoroborate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: potassium [4-(cyclohexyl(hydroxyl)methyl)phenyl]trifluoroborate
• 英文别名: potassium 4-(cyclohexyl(hydroxy)methyl)phenyl trifluoroborate；Potassium;[4-[cyclohexyl(hydroxy)methyl]phenyl]-trifluoroboranuide
• 化学式: C₁₃H₁₇BF₃O*K
• 分子量: 296.182
• InChiKey: BTRQBNNMDUUROT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium [4-(cyclohexyl(hydroxyl)methyl)phenyl]trifluoroborate 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以65%的产率得到potassium [4-(cyclohexylcarbonyl)phenyl]trifluoroborate
  参考文献：
  名称：

  One-pot preparation of hydroxylated potassium organotrifluoroborates and subsequent Jones oxidation to potassium organocarbonyltrifluoroborates

  摘要：

  Alcohol-containing potassium organotrifluoroborates as starting reagents were prepared from their corresponding dibromobenzenes through a sequential one-pot reaction. The oxidation reactions of these substrates, which were carried out using 3.0 equiv of 8 N Jones reagent in acetone at 0 degrees C, provided a high yield of the desired carbonyl-functionalized compounds. In addition, the cross-coupling reactions of these organocarbonyltrifluoroborates were successfully performed in the presence of 3 mol % of Pd (PPh3)(4) catalyst at 100 degrees C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.049
• 作为产物：
  描述：

  1,4-二溴苯 、 环己烷基甲醛 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 以78%的产率得到potassium [4-(cyclohexyl(hydroxyl)methyl)phenyl]trifluoroborate
  参考文献：
  名称：

  One-pot preparation of hydroxylated potassium organotrifluoroborates and subsequent Jones oxidation to potassium organocarbonyltrifluoroborates

  摘要：

  Alcohol-containing potassium organotrifluoroborates as starting reagents were prepared from their corresponding dibromobenzenes through a sequential one-pot reaction. The oxidation reactions of these substrates, which were carried out using 3.0 equiv of 8 N Jones reagent in acetone at 0 degrees C, provided a high yield of the desired carbonyl-functionalized compounds. In addition, the cross-coupling reactions of these organocarbonyltrifluoroborates were successfully performed in the presence of 3 mol % of Pd (PPh3)(4) catalyst at 100 degrees C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.049

文献信息

• Linchpin Synthons:  Metalation of Aryl Bromides Bearing a Potassium Trifluoroborate Moiety
  作者：Gary A. Molander、Noel M. Ellis

  DOI：10.1021/jo061324u

  日期：2006.9.1

  Aryl bromides bearing a potassium trifluoroborate moiety were subjected to lithium-halogen exchange at low temperature using a variety of alkyllithium reagents. A number of different electrophiles were evaluated in their reactions with the aryllithiums produced therein. Under carefully optimized conditions, potassium bromophenyl trifluoroborates afforded good to excellent yields of the corresponding alcohols (64-94% isolated yield) when aldehydes or ketones were used as the electophilic partner. Esters were unfortunately found to be unreactive.
• One-pot preparation of hydroxylated potassium organotrifluoroborates and subsequent Jones oxidation to potassium organocarbonyltrifluoroborates
  作者：Dong-Su Kim、Krishnavenu Bolla、Seokjoon Lee、Jungyeob Ham

  DOI：10.1016/j.tet.2010.12.049

  日期：2011.2

  Alcohol-containing potassium organotrifluoroborates as starting reagents were prepared from their corresponding dibromobenzenes through a sequential one-pot reaction. The oxidation reactions of these substrates, which were carried out using 3.0 equiv of 8 N Jones reagent in acetone at 0 degrees C, provided a high yield of the desired carbonyl-functionalized compounds. In addition, the cross-coupling reactions of these organocarbonyltrifluoroborates were successfully performed in the presence of 3 mol % of Pd (PPh3)(4) catalyst at 100 degrees C. (C) 2010 Elsevier Ltd. All rights reserved.