N-benzyl-3,5-bis(trifluoromethyl)benzamide | 827034-75-3

• 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-benzyl-3,5-bis(trifluoromethyl)benzamide
• CAS: 827034-75-3
• 化学式: C₁₆H₁₁F₆NO
• 分子量: 347.26
• InChiKey: NLISICZHMWHDPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-benzyl-3,5-bis(trifluoromethyl)benzamide 在 盐酸 、 chlorobis(cyclooctene)-iridium(I) dimer 、 二乙基硅烷 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 N-benzyl-1-(3,5-bis(trifluoromethyl)phenyl)methanamine
  参考文献：
  名称：

  Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane

  摘要：

  Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE)(2)Cl](2) with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.

  DOI：

  10.1021/ja304547s
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲酸 在 sodium fluoride 、 N,N-二异丙基乙胺 、 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 反应 26.0h， 生成 N-benzyl-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  使用XtalFluor-E的NaF辅助脱氧氟化从羧酸中合成酰基氟。

  摘要：

  描述了使用XtalFluor-E通过羧酸的脱氧氟化反应合成酰基氟。这种转变在催化量的NaF的辅助下在室温下于EtOAc中发生，其中XtalFluor-E充当活化剂和氟化物源。在硅胶垫上简单过滤后，可获得中等至极好的收率（36-99％）的各种酰基氟。我们还证明了顺序脱氧氟化/酰胺化是可能的。

  DOI：

  10.1021/acs.joc.0c01377

文献信息

• Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives
  作者：Anthony R. Prosser、Joseph E. Banning、Marina Rubina、Michael Rubin

  DOI：10.1021/ol101228k

  日期：2010.9.17

  A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

  描述了用仲酰胺对2-溴环丙基羧酰胺进行正式亲核取代的化学和非对映选择性方案。该方法允许反式-β-氨基环丙烷羧酸衍生物的收敛和高度选择性的合成。
• Nickel-catalyzed 1,4-aryl rearrangement of aryl <i>N</i>-benzylimidates <i>via</i> C–O and C–H bond cleavage
  作者：Satoshi Ogawa、Mamoru Tobisu

  DOI：10.1039/d2cc02355e

  日期：——

  We report herein that nickel-catalyzed reaction of aryl imidates bearing an N-benzyl group results in 1,4-migration of an O-aryl group via the cleavage of C–O and C–H bonds. This protocol allows for the benzylic C–H bond arylation of benzylamine building blocks using phenols as an aryl source to form elaborate diarylmethylamine derivatives.

  我们在此报道了带有N-苄基的芳基亚胺酯的镍催化反应通过C-O 和 C-H 键的断裂导致O-芳基的 1,4-迁移。该协议允许使用苯酚作为芳基来源对苄胺结构单元进行苄基 C-H 键芳基化，以形成精细的二芳基甲胺衍生物。
• Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles
  作者：Joseph E. Banning、Jacob Gentillon、Pavel G. Ryabchuk、Anthony R. Prosser、Andrew Rogers、Andrew Edwards、Andrew Holtzen、Ivan A. Babkov、Marina Rubina、Michael Rubin

  DOI：10.1021/jo4011798

  日期：2013.8.2

  A highly chemo- and diastereoselective protocol toward amino-substituted donor acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cydopropylamine derivatives.
• Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E
  作者：Marie Gonay、Chloé Batisse、Jean-François Paquin

  DOI：10.1021/acs.joc.0c01377

  日期：2020.8.7

  The synthesis of acyl fluorides using the deoxofluorination reaction of carboxylic acids using XtalFluor-E is described. This transformation, assisted by a catalytic amount of NaF, occurs at room temperature in EtOAc, where XtalFluor-E behaves as the activating agent and the fluoride source. A wide range of acyl fluorides were obtained in moderate to excellent yields (36–99%) after a simple filtration

  描述了使用XtalFluor-E通过羧酸的脱氧氟化反应合成酰基氟。这种转变在催化量的NaF的辅助下在室温下于EtOAc中发生，其中XtalFluor-E充当活化剂和氟化物源。在硅胶垫上简单过滤后，可获得中等至极好的收率（36-99％）的各种酰基氟。我们还证明了顺序脱氧氟化/酰胺化是可能的。
• Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane
  作者：Chen Cheng、Maurice Brookhart

  DOI：10.1021/ja304547s

  日期：2012.7.18

  Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE)(2)Cl](2) with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.