2-氟-5-硝基苯丙醇 | 91319-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氟-5-硝基苯丙醇
• 英文名称: 3-(2-fluoro-5-nitrophenyl)-1-propanol
• 英文别名: 3-(2-fluoro-5-nitrophenyl)propanol；3-(2-Fluoro-5-nitrophenyl)propan-1-ol
• CAS: 91319-51-6
• 化学式: C₉H₁₀FNO₃
• 分子量: 199.182
• InChiKey: VUDCHEGYZXXBBD-UHFFFAOYSA-N

物化性质

• 熔点：
  35-36 °C
• 沸点：
  342.6±27.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氟-5-硝基苯丙醇 在 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 乙醚 、 丙酮 为溶剂， 反应 12.0h， 以90%的产率得到2-(3-bromopropyl)-1-fluoro-4-nitrobenzene
  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：

  3-(2-fluoro-5-nitrophenyl)propanoic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2-氟-5-硝基苯丙醇
  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

• 6-Nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-S_NAr reaction
  作者：Richard A. Bunce、Takahiro Nago

  DOI：10.1002/jhet.5570450433

  日期：2008.7

  A tandem reductive amination-SNAr reaction has been developed for the synthesis of 6-nitro-1,2,3,4-tetrahydroquinolines. Treatment of 4-(2-fluoro-5-nitrophenyl)-2-butanone or 3-(2-fluoro-5-nitrophenyl)-propanal with primary amines and sodium cyanoborohydride in methanol at room temperature provided good to excellent yields of the substituted tetrahydroquinolines. The reaction proceeded best with the

  一种串联还原胺化-S Ñ氩反应已发展为6-硝基-1,2,3,4-四氢喹啉的合成。在室温下在甲醇中用伯胺和氰基硼氢化钠处理4-（2-氟-5-硝基苯基）-2-丁酮或3-（2-氟-5-硝基苯基）-丙醛提供了优异的优良取代基收率四氢喹啉。使用在α-碳上未分支的伯胺，反应在酮底物上进行得最好。醛还产生目标杂环，但这些杂环伴随有10-15％的未环化侧链还原胺化产物。
• Houghton, Roy P.; Voyle, Martyn; Price, Raymond, Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 925 - 931
  作者：Houghton, Roy P.、Voyle, Martyn、Price, Raymond

  DOI：——

  日期：——
• 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.