N-(1-adamantyl)-4-(tert-butyl)benzamide | 331434-35-6

• 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-(1-adamantyl)-4-(tert-butyl)benzamide
• 英文别名: N-(1-adamantyl)-4-tert-butylbenzamide
• CAS: 331434-35-6
• 化学式: C₂₁H₂₉NO
• 分子量: 311.467
• InChiKey: SRMSWFKRQAYMNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯胺 、 N-(1-adamantyl)-4-(tert-butyl)benzamide 在 Cp*Ir(OAc)₂ 、 copper diacetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以76%的产率得到4-adamantyl-N-butyl-2-(4-(trifluoromethyl)phenylamino)benzamide
  参考文献：
  名称：

  Iridium-Catalyzed C–H Amination with Anilines at Room Temperature: Compatibility of Iridacycles with External Oxidants

  摘要：

  Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.

  DOI：

  10.1021/ja502270y
• 作为产物：
  描述：

  金刚烷胺 、 对叔丁基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(1-adamantyl)-4-(tert-butyl)benzamide
  参考文献：
  名称：

  Iridium-Catalyzed C–H Amination with Anilines at Room Temperature: Compatibility of Iridacycles with External Oxidants

  摘要：

  Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.

  DOI：

  10.1021/ja502270y

文献信息

• Synthesis of Secondary Amides from Thiocarbamates
  作者：Pieter Mampuys、Eelco Ruijter、Romano V. A. Orru、Bert U. W. Maes

  DOI：10.1021/acs.orglett.8b01654

  日期：2018.7.20

  The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation

  据报道，由易于获得且稳定的取代的S-苯基硫代氨基甲酸酯和格氏试剂可合成仲酰胺。氧化后处理使得硫醇盐离去基团以二苯基二硫化物形式再循环。可以将二苯基二硫化物转化为S-苯基苯硫代磺酸盐，这是硫代氨基甲酸酯合成所需的反应物。这种酰胺合成适合于制备经典方法无法或几乎无法获得的具有挑战性的酰胺。
• Iridium-Catalyzed Direct C–H Amination with Alkylamines: Facile Oxidative Insertion of Amino Group into Iridacycle
  作者：Hyunwoo Kim、Sukbok Chang

  DOI：10.1021/acscatal.5b02165

  日期：2015.11.6

  Described herein is the development of Cp*Ir-(III)-catalyzed direct arene C-H amination using alkylamines as an amino source. This C-N bond formation showcases a notable example of cross-dehydrogenative coupling to install an amino functionality at the ortho-position of benzamide substrates. Mechanistic studies including the isolation of an amine-bound iridacyclic intermediate along with a set of chemical oxidations demonstrated the Ir-catalyzed inner-sphere C-H amination with primary alkylamines for the first time.
• Iridium-Catalyzed C–H Amination with Anilines at Room Temperature: Compatibility of Iridacycles with External Oxidants
  作者：Hyunwoo Kim、Kwangmin Shin、Sukbok Chang

  DOI：10.1021/ja502270y

  日期：2014.4.23

  Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.