4-(nitromethyl)quinoline | 22918-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(nitromethyl)quinoline
• 英文别名: 4-nitromethylquinoline；4-nitromethyl-quinoline；4-Nitromethylchinolin；4-(Nitromethyl)quinoline
• CAS: 22918-11-2
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: SZQIQRGCQAIYRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(nitromethyl)quinoline 在 乙酸铵 、 Selectfluor 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以96%的产率得到4-(difluoronitromethyl)-quinoline
  参考文献：
  名称：

  Sonochemical fluorination of heterocyclic nitro compounds with Selectfluor™ (F-TEDA-BF4)

  摘要：

  CH and CH2 groups attached to a heterocycle and a nitro function were rapidly mono- or difluorinated by reaction with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis-tetrafluoroborate (Selectfluor) in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), preferably with Ultrasonic irradiation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.037
• 作为产物：
  描述：

  4-甲基喹啉 在 lithium diisopropyl amide 、 硝酸甲酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 以85%的产率得到4-(nitromethyl)quinoline
  参考文献：
  名称：

  Fluorination and chlorination of nitroalkyl groups

  摘要：

  Heterocycles substituted with a nitromethyl (CH2NO2) or phenyl-nitromethyl (CHPhNO2) group were prepared by reaction of a methyl- or phenylmethyl-substituted heterocycle, respectively, with lithium di-isopropylamide followed by quenching the intermediate carbanion with methyl nitrate. Conversion of CH2NO2 attached to an alkyl or aryl moiety into a dichloronitromethyl (CCl2NO2) group was achieved using N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) in dichloromethane. Similarly, CH2NO2 attached to an alkyl or aryl group was converted into difluoronitromethyl (CF2NO2) using either 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis( tetrafluoroborate) (Selectfluor (TM)) or N-fluorobenzenesulfonimide with DBU as base and dichloromethane as solvent. Reaction of omega-nitroacetophenone with Selectfluor/DBU in dimethylformamide followed by acidification and distillation gave the parent difluoronitromethane in a useful 'one-pot' procedure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.020

文献信息

• Sonochemical fluorination of heterocyclic nitro compounds with Selectfluor
  作者：Majid M. Sadeghi、Hossein Loghmani-Khouzani、Reza Ranjbar-Karimi、Philip Butler、Bernard T. Golding

  DOI：10.1016/j.tetlet.2006.03.144

  日期：2006.6
• Fluorination and chlorination of nitroalkyl groups
  作者：Philip Butler、Bernard T. Golding、Gilles Laval、Hossein Loghmani-Khouzani、Reza Ranjbar-Karimi、Majid M. Sadeghi

  DOI：10.1016/j.tet.2007.08.020

  日期：2007.11

  Heterocycles substituted with a nitromethyl (CH2NO2) or phenyl-nitromethyl (CHPhNO2) group were prepared by reaction of a methyl- or phenylmethyl-substituted heterocycle, respectively, with lithium di-isopropylamide followed by quenching the intermediate carbanion with methyl nitrate. Conversion of CH2NO2 attached to an alkyl or aryl moiety into a dichloronitromethyl (CCl2NO2) group was achieved using N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) in dichloromethane. Similarly, CH2NO2 attached to an alkyl or aryl group was converted into difluoronitromethyl (CF2NO2) using either 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis( tetrafluoroborate) (Selectfluor (TM)) or N-fluorobenzenesulfonimide with DBU as base and dichloromethane as solvent. Reaction of omega-nitroacetophenone with Selectfluor/DBU in dimethylformamide followed by acidification and distillation gave the parent difluoronitromethane in a useful 'one-pot' procedure. (c) 2007 Elsevier Ltd. All rights reserved.
• Sonochemical fluorination of heterocyclic nitro compounds with Selectfluor™ (F-TEDA-BF4)
  作者：Majid M. Sadeghi、Hossein Loghmani-Khouzani、Reza Ranjbar-Karimi、Bernard T. Golding

  DOI：10.1016/j.tetlet.2006.01.037

  日期：2006.4

  CH and CH2 groups attached to a heterocycle and a nitro function were rapidly mono- or difluorinated by reaction with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis-tetrafluoroborate (Selectfluor) in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), preferably with Ultrasonic irradiation. (c) 2006 Elsevier Ltd. All rights reserved.