2-(2-fluoro-5-nitrobenzyl)-1,3-propanoic acid | 683215-78-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(2-fluoro-5-nitrobenzyl)-1,3-propanoic acid
• 英文别名: 2-[(2-Fluoro-5-nitrophenyl)methyl]propanedioic acid
• CAS: 683215-78-3
• 化学式: C₁₀H₈FNO₆
• 分子量: 257.175
• InChiKey: VYACZFNJHLWWJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-fluoro-5-nitrobenzyl)-1,3-propanoic acid 反应 0.5h， 以94%的产率得到3-(2-fluoro-5-nitrophenyl)propanoic acid
  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
• 作为产物：
  描述：

  di-tert-butyl 2-(2-fluoro-5-nitrobenzyl)-1,3-propanedioate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到2-(2-fluoro-5-nitrobenzyl)-1,3-propanoic acid
  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.