N,N-diethylammonium methyltrifluoroborate | 1268340-96-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diethylammonium methyltrifluoroborate
• 英文别名: N,N-diethyltrifluoroboratomethylamine internal salt；[(diethylammonio)methyl]trifluoroborate；(Diethylazaniumyl)methyl-trifluoroboranuide
• CAS: 1268340-96-0
• 化学式: C₅H₁₂BF₃N*H
• 分子量: 154.971
• InChiKey: KIODRGYVLULDDN-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  4.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯吡啶 、 N,N-diethylammonium methyltrifluoroborate 在 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 45.0h， 以30%的产率得到3-((二乙基氨基)甲基)吡啶
  参考文献：
  名称：

  Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

  DOI：

  10.1021/jo2001066
• 作为产物：
  描述：

  碘甲基硼酸频哪醇酯 、 二乙胺 在 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.58h， 生成 N,N-diethylammonium methyltrifluoroborate
  参考文献：
  名称：

  从几分钟到几年：预测有机三氟硼酸盐的溶剂分解速率

  摘要：

  有机三氟硼酸盐在水中的溶解速度超过五个数量级。溶剂化速率常数的负对数，P ķ （B  F） ，关联格外好与p ķ一个类似的羧酸（共- [R 2 = 0.984）。这种不可预见的相关性可能对一些应用具有预测价值，包括Suzuki-Miyaura交叉偶联反应和18 F-有机三氟硼酸酯放射修复基团的设计。

  DOI：

  10.1002/chem.201405829

文献信息

• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Ammonio- and Amidomethyltrifluoroborates
  作者：Gary A. Molander、Floriane Beaumard

  DOI：10.1021/ol200128y

  日期：2011.3.4

  A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp(2)-Csp(3) Suzuki-Miyaura cross-coupling with potassium ammonio- and amidomethyltrifluoroborates to afford the corresponding products in high yields.
• From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates
  作者：Zhibo Liu、Daniel Chao、Ying Li、Richard Ting、Jihyoon Oh、David M. Perrin

  DOI：10.1002/chem.201405829

  日期：2015.3.2

  Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, pk(BF), correlates exceptionally well with the pKa of the analogous carboxylic acid (R2=0.984). This unforeseen correlation may be of predictive value for several applications including Suzuki–Miyaura cross‐coupling reactions and the design of 18F‐organotrifluoroborate

  有机三氟硼酸盐在水中的溶解速度超过五个数量级。溶剂化速率常数的负对数，P ķ （B  F） ，关联格外好与p ķ一个类似的羧酸（共- [R 2 = 0.984）。这种不可预见的相关性可能对一些应用具有预测价值，包括Suzuki-Miyaura交叉偶联反应和18 F-有机三氟硼酸酯放射修复基团的设计。
• Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions
  作者：Jessica Raushel、Deidre L. Sandrock、Kanth V. Josyula、Deborah Pakyz、Gary A. Molander

  DOI：10.1021/jo2001066

  日期：2011.4.15

  A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.