2-phenyl-4-trifluoromethyl-3H-benzo[b][1,4]diazepine | 53511-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-phenyl-4-trifluoromethyl-3H-benzo[b][1,4]diazepine
• 英文别名: 4-phenyl-2-trifluoromethyl-3H-1,5-benzodiazepine；2-phenyl-4-trifluoromethyl-1(5)H-benzo[b][1,4]diazepine；2-phenyl-4-(trifluoromethyl)-3H-1,5-benzodiazepine
• CAS: 53511-21-0
• 化学式: C₁₆H₁₁F₃N₂
• 分子量: 288.272
• InChiKey: GINNNEPKZPSKNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-4-(2-Amino-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以90%的产率得到2-phenyl-4-trifluoromethyl-3H-benzo[b][1,4]diazepine
  参考文献：
  名称：

  REACTIONS OF β-ALKOXYVINYL TRIFLUOROMETHYL KETONES. THE SYNTHESIS OF N-[1-ARYL-3-OXO-4,4,4-TRIFLUORO-1-BUTEN-1-YL]-o-PHENYLENEDIAMINES AND 4-ARYL-2-TRIFLUOROMETHYL-3H-1,5-BENZODIAZEPINES

  摘要：

  A series of five N-[1-aryl-3-oxo-4,4,4-trifluoro-1-buten-1-yl]-o-phenylenediamines 2 [CF3COCH=C(R)NH-o-PhNH2], where R=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh from the reaction of beta-aryl-beta-methoxyvinyl trifluoromethyl ketones 1 with o-phenylenediamine was prepared and isolated in good yield (59-71%). Another series of five 4-aryl-2-trifluoromethyl-3H-1,5-benzodiazepines 3, where aryl=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh was also obtained in an one-step reaction from ketones 1 by an intramolecular cyclization reaction with o-phenylenediamine under mild acid conditions in good yields (60-77%).

  DOI：

  10.1081/scc-120013748

文献信息

• Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol
  作者：V. I. Filyakova、N. S. Boltacheva、D. V. Sevenard、V. N. Charushina

  DOI：10.1007/s11172-010-0314-x

  日期：2010.9

  synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene in an MeOH-AcOH-HCl mixture at 0 °C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major products, whereas the reaction with 2-aminothiophenol

  摘要 1,3-二酮酸锂与1,2-二氨基苯和2,3-二氨基萘在甲醇中反应合成了1,5-苯并[b]-和1,5-萘并[2,3-b]二氮杂-AcOH-HCl 混合物在 0 °C。含氟烷基的 1,3-二酮酸锂与 1,2-二氨基苯和 1,2-二氨基-4,5-二氟苯在乙酸中回流反应，主要产物为含 2-氟烷基的苯并咪唑，而反应与 2-氨基苯硫酚生成 2-苯基苯并噻唑。含有环己烷和环戊烷部分的二酮酸锂与 1,2-二氨基芳烃和 2-氨基苯硫醇的反应伴随着碳环的打开形成 2-(6-氧代-7,7,7-三氟庚基)苯并咪唑和 2- (5-氧代-6,6,6-三氟己基)苯并噻唑水合物。
• Synthesis of trifluoromethylated [1,4]diazepines from 1,1,1-trifluoroalk-3-yn-2-ones
  作者：Alexey R. Romanov、Alexander Yu. Rulev、Igor A. Ushakov、Vasiliy M. Muzalevskiy、Valentine G. Nenajdenko

  DOI：10.1016/j.mencom.2014.09.007

  日期：2014.9

  Reaction of 1,1,1-trifluoroalk-3-yn-2-ones with 1,2-diamines affords trifluoromethylated [1,4]diazepines.
• REACTIONS OF β-ALKOXYVINYL TRIFLUOROMETHYL KETONES. THE SYNTHESIS OF <i>N</i>-[1-ARYL-3-OXO-4,4,4-TRIFLUORO-1-BUTEN-1-YL]-<i>o</i>-PHENYLENEDIAMINES AND 4-ARYL-2-TRIFLUOROMETHYL-<i>3H</i>-1,5-BENZODIAZEPINES
  作者：Helio Gauze Bonacorso、Livete Magali Leão Marques、Nilo Zanatta、Marcos Antonio Pinto Martins

  DOI：10.1081/scc-120013748

  日期：2002.1.1

  A series of five N-[1-aryl-3-oxo-4,4,4-trifluoro-1-buten-1-yl]-o-phenylenediamines 2 [CF3COCH=C(R)NH-o-PhNH2], where R=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh from the reaction of beta-aryl-beta-methoxyvinyl trifluoromethyl ketones 1 with o-phenylenediamine was prepared and isolated in good yield (59-71%). Another series of five 4-aryl-2-trifluoromethyl-3H-1,5-benzodiazepines 3, where aryl=Ph, 4-MePh, 4-BrPh, 4-ClPh, 4-OMePh was also obtained in an one-step reaction from ketones 1 by an intramolecular cyclization reaction with o-phenylenediamine under mild acid conditions in good yields (60-77%).