1-benzyl-7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepine | 1021389-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-benzyl-7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: 1-Benzyl-7-nitro-2,3,4,5-tetrahydro-1-benzazepine
• CAS: 1021389-60-5
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: HZVNXUFKKXISSQ-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-bromobutyl)-1-fluoro-4-nitrobenzene 、 苄胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以35%的产率得到1-benzyl-7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Benzo‐fused heterocycles and carbocycles by intramolecular S _N Ar and tandem S _N 2‐S _N Ar reactions

  摘要：

  Abstractmagnified imageBenzo‐fused heterocyclic and carbocyclic systems have been synthesized by intramolecular SNAr and tandem SN2‐SNAr reactions. Treatment of 3‐(2‐fluoro‐5‐nitrophenyl)‐1‐propanol with sodium hydride in N,N‐dimethylformamide gave 6‐nitrochroman in 80% yield by an intramolecular SNAr reaction. Treatment of 2‐(3‐bromopropyl)‐1‐fluoro‐4‐nitrobenzene with benzylamine in N,N‐dimethylformamide gave 1‐benzyl‐6‐nitrotetrahydroquinoline in 98% yield by a tandem SN2‐SNAr reaction. Finally, in a similar process, reaction of this same bromide with dimethyl malonate under basic conditions gave 1,1‐bis(methoxycarbonyl)‐6‐nitro‐1,2,3,4‐tetrahydronaphthalene in 80% yield. Further studies exploring ring size effects are also presented.

  DOI：

  10.1002/jhet.5570450239

文献信息

• Benzo‐fused heterocycles and carbocycles by intramolecular S _N Ar and tandem S _N 2‐S _N Ar reactions
  作者：Richard A. Bunce、Takahiro Nago、Nathan Sonobe、Legrande M. Slaughter

  DOI：10.1002/jhet.5570450239

  日期：2008.3

  Abstractmagnified imageBenzo‐fused heterocyclic and carbocyclic systems have been synthesized by intramolecular SNAr and tandem SN2‐SNAr reactions. Treatment of 3‐(2‐fluoro‐5‐nitrophenyl)‐1‐propanol with sodium hydride in N,N‐dimethylformamide gave 6‐nitrochroman in 80% yield by an intramolecular SNAr reaction. Treatment of 2‐(3‐bromopropyl)‐1‐fluoro‐4‐nitrobenzene with benzylamine in N,N‐dimethylformamide gave 1‐benzyl‐6‐nitrotetrahydroquinoline in 98% yield by a tandem SN2‐SNAr reaction. Finally, in a similar process, reaction of this same bromide with dimethyl malonate under basic conditions gave 1,1‐bis(methoxycarbonyl)‐6‐nitro‐1,2,3,4‐tetrahydronaphthalene in 80% yield. Further studies exploring ring size effects are also presented.