2-(methylamino)-N-(2-(trifluoromethyl)phenyl)benzamide | 348613-34-3

• 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: 2-(methylamino)-N-(2-(trifluoromethyl)phenyl)benzamide
• 英文别名: 2-(methylamino)-N-[2-(trifluoromethyl)phenyl]benzamide
• CAS: 348613-34-3
• 化学式: C₁₅H₁₃F₃N₂O
• 分子量: 294.276
• InChiKey: YETLMYHXITWXTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-甲基-2-噻吩甲醛 、 2-(methylamino)-N-(2-(trifluoromethyl)phenyl)benzamide 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以69%的产率得到1-methyl-2-(5-methylthiophen-2-yl)-3-[2-(trifluoromethyl)phenyl]-2H-quinazolin-4-one
  参考文献：
  名称：

  N-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin

  摘要：

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.

  DOI：

  10.1021/jm4002346
• 作为产物：
  描述：

  邻氨基三氟甲苯 、 1-甲基苯唑 在 溶剂黄146 作用下， 生成 2-(methylamino)-N-(2-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Scaffold‐Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst‐Controlled Assembly of a Pharmaceutically Relevant Atropisomer

  摘要：

  A new class of superbasic, bifunctional peptidyl guanidine catalysts is presented, which enables the organocatalytic, atroposelective synthesis of axially chiral quinazolinediones. Computational modeling unveiled the conformational modulation of the catalyst by a novel phenyl urea N‐cap, that preorganizes the structure into the active, folded state. A previously unanticipated noncovalent interaction involving a difluoroacetamide acting as a hybrid mono‐ or bidentate hydrogen bond donor emerged as a decisive control element inducing atroposelectivity. These discoveries spurred from a scaffold‐oriented project inspired from a fascinating investigational BTK inhibitor featuring two stable chiral axes and relies on a mechanistic framework that was foreign to the extant lexicon of asymmetric catalysis.

  DOI：

  10.1002/chem.202401109