potassium 2,2-dicyanoethyltrifluoroborate | 888711-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: potassium 2,2-dicyanoethyltrifluoroborate
• 英文别名: Potassium (2,2-dicyanoethyl)trifluoroborate；potassium;2,2-dicyanoethyl(trifluoro)boranuide
• CAS: 888711-56-6
• 化学式: C₄H₃BF₃N₂*K
• mdl: MFCD18459321
• 分子量: 185.986
• InChiKey: JLFULSNEXVEXDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium 2,2-dicyanoethyltrifluoroborate 、 2-碘丁烷 在 sodium hydride 、 potassium hydrogen bifluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到potassium 2,2-dicyano-3-methylpentyltrifluoroborate
  参考文献：
  名称：

  Facile Synthesis of Highly Functionalized Ethyltrifluoroborates

  摘要：

  Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)(2)CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

  DOI：

  10.1021/jo800760f
• 作为产物：
  描述：

  碘甲基硼酸频哪醇酯 、 丙二腈 在 sodium hydride 、 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 13.0h， 以52%的产率得到potassium 2,2-dicyanoethyltrifluoroborate
  参考文献：
  名称：

  Facile Synthesis of Highly Functionalized Ethyltrifluoroborates

  摘要：

  Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)(2)CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

  DOI：

  10.1021/jo800760f

文献信息

• Synthesis of Functionalized Organotrifluoroborates via Halomethyltrifluoroborates
  作者：Gary A. Molander、Jungyeob Ham

  DOI：10.1021/ol060375a

  日期：2006.5.1

  Potassium bromo- and iodomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF2. Moreover, a new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of the halide in these potassium halomethyltrifluoroborates is described.
• Facile Synthesis of Highly Functionalized Ethyltrifluoroborates
  作者：Gary A. Molander、Wilma Febo-Ayala、Montserrat Ortega-Guerra

  DOI：10.1021/jo800760f

  日期：2008.8.1

  Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)(2)CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.