4-propenyltetrafluoropyridine | 72378-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-propenyltetrafluoropyridine
• 英文别名: 2,3,5,6-Tetrafluor-4-trans-propenyl-pyridin；2,3,5,6-Tetrafluor-4-cis-propenyl-pyridin；2,3,5,6-Tetrafluor-4-propenyl-pyridin；2,3,5,6-Tetrafluoro-4-prop-1-enylpyridine
• CAS: 72378-95-1
• 化学式: C₈H₅F₄N
• 分子量: 191.128
• InChiKey: SWJVMEJEAOZOAF-UHFFFAOYSA-N

物化性质

• 沸点：
  174.1±35.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-propenyltetrafluoropyridine 在 盐酸羟胺 、 臭氧 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 tetrafluoropyridine-4-aldoxime
  参考文献：
  名称：

  Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

  摘要：

  Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pK(a)) and second-order rate constants (k(ox)-) of the fluorinated pyridinealdoximes towards satin were measured. 2,3,5,6-Tetrafluoropyridine-4-aldoxime had the best profile: its k(ox)- approached that of the therapeutic oxime P2S (310 vs. 120 l mol(-1) min(-1)), but its higher pK(a) (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK(a) nearer to 8 and enhance their therapeutic potential. Crown Copyright (c) 2011 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.05.028
• 作为产物：
  描述：

  nonafluoro-2,3,4,5-tetrahydropyridine 以 乙醚 为溶剂， 生成 4-propenyltetrafluoropyridine
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.5, 4, page 115 - 148

  摘要：

  DOI：

文献信息

• Fluoropyridines and derivatives
  申请人：HASZELDINE ROBERT N

  公开号：US03317542A1

  公开（公告）日：1967-05-02

  The invention comprises 2,3,5,6-tetrafluoropyridine -4-carboxylic acid and the preparation thereof by oxidizing 2,3,5,6-tetrafluoro-4-propenylpyridine with nitric acid. The 4-carboxylic acid can be decarboxylated by heating to 2,3,5,6-tetrafluoropyridine. The s-benzylthiouronium derivative of the acid is obtained by reacting the acid with s-benzylthiouronium chloride.

  该发明包括2,3,5,6-四氟吡啶-4-羧酸及其通过用硝酸氧化2,3,5,6-四氟-4-丙烯基吡啶来制备。4-羧酸可以通过加热转化为2,3,5,6-四氟吡啶。酸的s-苄基硫代脲衍生物是通过将酸与s-苄基硫代脲氯化物反应获得的。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.5, 4, page 115 - 148
  作者：

  DOI：——

  日期：——
• Banks, R. E.; Burgess, J. E.; Cheng, W. M., Journal of the Chemical Society
  作者：Banks, R. E.、Burgess, J. E.、Cheng, W. M.、Haszeldine, R. N.

  DOI：——

  日期：——
• Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning
  作者：Christopher M. Timperley、R. Eric Banks、Ian M. Young、Robert N. Haszeldine

  DOI：10.1016/j.jfluchem.2011.05.028

  日期：2011.8

  Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pK(a)) and second-order rate constants (k(ox)-) of the fluorinated pyridinealdoximes towards satin were measured. 2,3,5,6-Tetrafluoropyridine-4-aldoxime had the best profile: its k(ox)- approached that of the therapeutic oxime P2S (310 vs. 120 l mol(-1) min(-1)), but its higher pK(a) (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK(a) nearer to 8 and enhance their therapeutic potential. Crown Copyright (c) 2011 Published by Elsevier B.V. All rights reserved.