2,2-dimethyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanamide | 1416775-71-7

• 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: 2,2-dimethyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanamide
• CAS: 1416775-71-7
• 化学式: C₁₇H₂₆BNO₃
• 分子量: 303.209
• InChiKey: FVJMJGJYZDNFNA-UHFFFAOYSA-N

物化性质

• 沸点：
  453.8±28.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanamide 在 1-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate 、 (tBuCN)2Cu*OTf 、 silver fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以64%的产率得到N-(3-氟-苯基)-2,2-二甲基-丙酰胺
  参考文献：
  名称：

  [EN] FLUORINATION OF ARYL COMPOUNDS
  [FR] FLUORATION DE COMPOSÉS ARYLES

  摘要：

  这项发明提供了一种在含有可被氟原子取代的离去基团的芳基前体中进行氟化的组合物和使用这些组合物的方法。这些组合物包括金属离子源、亲电性氟源、碱和一种化合物，该化合物是芳基氟化物的芳基前体，并且具有可被氟原子取代的离去基团。该发明的示例方法利用这些组合物和方法来制备芳基氟化物。在一个示例实施方式中，亲电性氟源是18F的源。

  公开号：

  WO2014107379A1
• 作为产物：
  描述：

  频哪醇 、 3-pivaloylaminophenylboronic acid 以 乙醚 为溶剂， 生成 2,2-dimethyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanamide
  参考文献：
  名称：

  Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex

  摘要：

  A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl- copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.

  DOI：

  10.1021/ja310909q

文献信息

• [EN] FLUORINATION OF ARYL COMPOUNDS<br/>[FR] FLUORATION DE COMPOSÉS ARYLES
  申请人：UNIV CALIFORNIA

  公开号：WO2014107379A1

  公开（公告）日：2014-07-10

  The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by a fluorine atom. The compositions include a metal ion source, a electrophilic fluorine source, a base, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluorine atom. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the electrophilic fluorine source is a source of 18F.

  这项发明提供了一种在含有可被氟原子取代的离去基团的芳基前体中进行氟化的组合物和使用这些组合物的方法。这些组合物包括金属离子源、亲电性氟源、碱和一种化合物，该化合物是芳基氟化物的芳基前体，并且具有可被氟原子取代的离去基团。该发明的示例方法利用这些组合物和方法来制备芳基氟化物。在一个示例实施方式中，亲电性氟源是18F的源。
• Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex
  作者：Patrick S. Fier、Jingwei Luo、John F. Hartwig

  DOI：10.1021/ja310909q

  日期：2013.2.20

  A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl- copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.