N-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)benzamide | 1299491-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)benzamide
• 英文别名: N-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl]benzamide
• CAS: 1299491-27-2
• 化学式: C₁₆H₁₂F₃NO₂
• 分子量: 307.272
• InChiKey: KXRCVYPNTUMLAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)benzamide 在 吡啶 、 盐酸 、 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 、 硫酸 、 (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene 、 水 、 氢气 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 20.0~80.0 ℃ 、5.07 MPa 条件下， 反应 25.33h， 生成 (R)-2-benzamido-1-(4-(trifluoromethyl)phenyl)ethyl (R)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

  摘要：

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

  DOI：

  10.1021/ja201543h
• 作为产物：
  描述：

  2-azido-1-(4-(trifluoromethyl)phenyl)ethanone 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.03h， 生成 N-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)benzamide
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

  摘要：

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

  DOI：

  10.1021/ja201543h

文献信息

• Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions
  作者：Cai Gao、Qianting Zhou、Li Yang、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.joc.0c01871

  日期：2020.11.6

  An efficient synthesis of α-amidoketone derivatives through the cascade reactions of carboxylic acids with vinyl azides is presented. Compared with literature protocols, notable features of this new method include catalyst-free conditions, broad substrate scope, good tolerance of a wide range of functional groups, and high efficiency. In addition, the synthetic potential of this method as a tool for

  提出了通过羧酸与叠氮化乙烯的级联反应有效合成α-酰胺酮衍生物的方法。与文献方法相比，该新方法的显着特征包括无催化剂条件，广泛的底物范围，对各种官能团的良好耐受性和高效率。另外，该方法作为后期修饰工具的合成潜力通过其在许多羧酸药物分子的结构修饰中的应用而令人信服。