5,5-difluoro-8,9,10,10a-tetrahydro-9-isopropyl-2-phenyl-2H-[1.2,4]triazolo[1,2-α]cinnoline-1,3(5H,7H)-dione | 1070912-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,5-difluoro-8,9,10,10a-tetrahydro-9-isopropyl-2-phenyl-2H-[1.2,4]triazolo[1,2-α]cinnoline-1,3(5H,7H)-dione
• CAS: 1070912-85-4
• 化学式: C₁₉H₂₁F₂N₃O₂
• 分子量: 361.391
• InChiKey: VQNRZZYEARMGPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48.93
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 (4S)-1-(2-bromo-2,2-difluoroethyl)-4-(2-bromoisopropyl)-cyclohexene 生成 4-(2-bromo-2,2-difluoroethyl)-1-isopropylcyclohexene 、 4-(2-bromo-2,2-difluoroethyl)-1-isopropylcyclohexane 、 5,5-difluoro-8,9,10,10a-tetrahydro-9-isopropyl-2-phenyl-2H-[1.2,4]triazolo[1,2-α]cinnoline-1,3(5H,7H)-dione
  参考文献：
  名称：

  Sodium dithionite initiated addition of CF2Br2 to β-pinene and reactions of the adduct

  摘要：

  Sodium dithionite effectively promotes the addition of dibromodifluoromethane to the exocyclic double bond of P-pinene. The reaction proceeded in a MeCN/H2O system to give almost quantitatively an adduct, 1-(2-bromo-2,2-difluoroethyl)-4-(2-bromoisopropyl)-cyclohexene, as the sole product. On treatment of the adduct with 2,2,6,6-tetramethylpiperidine elimination of HBr only from the (CH3)(2)CHBr group occurred to give a mixture of regioisomeric dienes, while treatment with 50% KOH under phase transfer catalysis conditions or with K2CO3 in DMF resulted in total dehydrobromination to give trienes possessing an exocyclic CH = CF2 group. Surprisingly, the main course of the reactions of the adduct with DBU (1,8-diazabicyclo[5.4.0]undece-7-ene) and also with t-BuOK in THF was elimination of HBr only from the CH2CF2Br group to afford 1-(2,2-difluorovinyl)-4-(2-bromoisopropyl)cyclohexene as the main product. Catalytic hydrogenation of the adduct followed by treatment with DBU afforded a conjugated diene, 1-(2,2-difluorovinyl)-4-isopropylcyclohexene. Compounds bearing the CH = CF2 group are new 1, 1 -difluorodienes which readily reacted with 4-phenyl-3H-1,2,4-triazoline-3,5-dione to give cycloadducts, derivatives of triazolo[1,2-alpha]cinnoline. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.07.004