2,3-dihydro-1,2,2-trimethyl-3-[N-(trifluoromethylsulfonyl)imino]5-phenyl-1H-benzo[e][1,4]diazepine

• 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: 2,3-dihydro-1,2,2-trimethyl-3-[N-(trifluoromethylsulfonyl)imino]5-phenyl-1H-benzo[e][1,4]diazepine
• 英文别名: 1,1,1-trifluoro-N-(1,2,2-trimethyl-5-phenyl-1,4-benzodiazepin-3-ylidene)methanesulfonamide
• 化学式: C₁₉H₁₈F₃N₃O₂S
• 分子量: 409.432
• InChiKey: XNGFPHLMLYIEFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  triflic azide 、 1-methyl-2-(1-methylethyl)-4-phenylquinazolinium hexafluorophosphate 在 air 、 potassium hydride 作用下， 以 苯 为溶剂， 以2%的产率得到1,2-dihydro-1-methyl-2-[N-(trifluoromethylsulfonyl)imino]-4-phenylquinazoline
  参考文献：
  名称：

  Ring Expansion of 2-Alkylidenedihydroquinazolines to Iminodihydro-1,4-benzodiazepines by Methanesulfonyl and Trifluoromethanesulfonyl Azide

  摘要：

  2-Alkyl-1 -methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluoromethanesulfonyl azide (5b) gives mixtures of colourless (15) and intensely yellow N-sulfonylimino-1,4-benzodiazepines 16 along with products due to cleavage of the exocyclic double bond of 10, viz. 11 and 13. The ethylidene compound 10b yields the bicyclic products 18 and 19, apparently by complex sequences of reactions that are triggered by removal of the acidic proton at C-2 of 16b and 16f. The structures of the products are based on spectroscopic evidence and X-ray diffraction analyses performed on 15b, 16d, 16e, and 19.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1577::aid-ejoc1577>3.0.co;2-6

文献信息

• Ring Expansion of 2-Alkylidenedihydroquinazolines to Iminodihydro-1,4-benzodiazepines by Methanesulfonyl and Trifluoromethanesulfonyl Azide
  作者：Helmut Quast、Svetlana Ivanova、Eva-Maria Peters、Karl Peters

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1577::aid-ejoc1577>3.0.co;2-6

  日期：2000.4

  2-Alkyl-1 -methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluoromethanesulfonyl azide (5b) gives mixtures of colourless (15) and intensely yellow N-sulfonylimino-1,4-benzodiazepines 16 along with products due to cleavage of the exocyclic double bond of 10, viz. 11 and 13. The ethylidene compound 10b yields the bicyclic products 18 and 19, apparently by complex sequences of reactions that are triggered by removal of the acidic proton at C-2 of 16b and 16f. The structures of the products are based on spectroscopic evidence and X-ray diffraction analyses performed on 15b, 16d, 16e, and 19.