N-(4-iodophenyl)-N-methylpivalamide | 1366392-16-6

• 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: N-(4-iodophenyl)-N-methylpivalamide
• 英文别名: N-(4-iodophenyl)-N,2,2-trimethylpropanamide
• CAS: 1366392-16-6
• 化学式: C₁₂H₁₆INO
• 分子量: 317.17
• InChiKey: GNFBYKBQSHCTKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-iodophenyl)-N-methylpivalamide 在 copper(I) trifluoromethanesulfonate bis(trimethylacetonitrile) complex 、 silver fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以62%的产率得到N-(4-fluorophenyl)-N-methylpivalamide
  参考文献：
  名称：

  Copper-Mediated Fluorination of Aryl Iodides

  摘要：

  The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.

  DOI：

  10.1021/ja304410x
• 作为产物：
  描述：

  三甲基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-(4-iodophenyl)-N-methylpivalamide
  参考文献：
  名称：

  芳基和乙烯基碘的铜介导的二氟甲基化

  摘要：

  选择性氟化分子作为材料、药物和农用化学品很重要，但通过简单、温和的实验室方法合成它们具有挑战性。我们报告了一种直接的方法，用于将芳基和乙烯基碘与由现成的试剂产生的二氟甲基进行交叉偶联，以形成二氟甲基芳烃和二氟甲基取代的烯烃。电子中性、富电子和位阻芳基和乙烯基碘与 CuI、CsF 和 TMSCF(2)H 的组合反应导致高产率形成二氟甲基取代的产物，具有良好的官能团兼容性。这种转变令人惊讶，部分原因是先前观察到 CuCF(2)H 的不稳定性。

  DOI：

  10.1021/ja301013h

文献信息

• [EN] DIFLUOROMETHYLATION OF ARYL AND VINYL IODIDES<br/>[FR] DIFLUOROMÉTHYLATION D'IODURES D'ARYLE ET DE VINYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2013134296A1

  公开（公告）日：2013-09-12

  Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.

  选择性氟化分子在材料、制药和农药中很重要，但通过简单、温和的实验室方法合成它们是具有挑战性的。我们报告了一种简单的方法，用于将二氟甲基基团与易得试剂进行交叉偶联，形成二氟甲基芳烃。电子中性、电子富集和空间位阻的芳基和乙烯基碘化物与Cul、CsF和TMSCF2H的组合反应导致了高产率的二氟甲基芳烃形成，并具有良好的官能团兼容性。这种转化令人惊讶，部分原因是之前观察到CuCF2H的不稳定性。
• [EN] FLUORINATION OF ARYL COMPOUNDS<br/>[FR] FLUORATION DE COMPOSÉS ARYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2013188554A1

  公开（公告）日：2013-12-19

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

  本发明提供了组合物和使用这些组合物的方法，用于氟化含有可被氟离子取代的离去基的芳基前体。这些组合物包括金属离子源、氟离子源和化合物，该化合物是芳基氟化物的芳基前体，并且具有可被氟离子取代的离去基。本发明的示例方法利用这些组合物和方法制备芳基氟化物化合物。在一个示例实施例中，氟离子源是18F的源。
• DIFLUOROMETHYLATION OF ARYL AND VINYL IODIDES
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150045580A1

  公开（公告）日：2015-02-12

  Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF 2 H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF 2 H.

  有选择性氟化的分子对于材料、制药和农药非常重要，但是通过简单、温和的实验室方法合成它们是具有挑战性的。我们报告了一种直接的方法，通过交叉偶联二氟甲基基团和易得到的试剂形成二氟甲基芳烃。电子中性、富电子和空间位阻的芳基和乙烯基碘化物与Cul、CsF和TMSCF2H的组合反应可以高产率地形成二氟甲基芳烃，并具有良好的官能团兼容性。这种转化令人惊讶，部分原因是因为之前观察到CuCF2H的不稳定性。
• FLUORINATION OF ARYL COMPOUNDS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150175508A1

  公开（公告）日：2015-06-25

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

  本发明提供了组合物及其在氟化含有可被氟离子替换的离去基的芳基前体中的使用方法。该组合物包括金属离子源、氟离子源和化合物，该化合物是芳基前体的芳基氟化物，其具有可被氟离子替换的离去基。本发明的示例方法利用这种组合物和方法制备芳基氟化物化合物。在一个示例实施例中，氟离子源是18F的源。
• US9452959B2
  申请人：——

  公开号：US9452959B2

  公开（公告）日：2016-09-27