3,5-dichloro-2,4-dimethoxy-6-fluoropyridine | 2693-58-5

• 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: 3,5-dichloro-2,4-dimethoxy-6-fluoropyridine
• 英文别名: 4,6-(CH3O)2-3,5-Cl2-C5FN；3,5-dichloro-2-fluoro-4,6-dimethoxy-pyridine；2,4-Dimethoxy-3,5-dichlor-6-fluorpyridin；3,5-Dichlor-2-fluor-4,6-dimethoxypyridin；3,5-Dichloro-2-fluoro-4,6-dimethoxypyridine
• CAS: 2693-58-5
• 化学式: C₇H₆Cl₂FNO₂
• 分子量: 226.035
• InChiKey: CRNXMVXLSDHVGX-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  234.9±35.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-2,4-dimethoxy-6-fluoropyridine 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2,4-Dimethoxy-6-[4-[3-(trifluoromethyl)phenoxy]phenoxy]pyridine
  参考文献：
  名称：

  Dimethoxypyrimidines as Novel Herbicides. Part 1. Synthesis and Herbicidal Activity of Dimethoxyphenoxyphenoxypyrimidines and Analogues

  摘要：

  A number of 6-(4-phenoxyphenoxy)pyrimidines and triazines were synthesized and their herbicidal activity was measured. Compounds with the methoxy groups at the 2- and 4-positions on the pyrimidine and triazine rings exhibited high herbicidal activity. Introduction of a substituent into the 5-position of the pyrimidine ring diminished the activity. In the phenoxyphenoxy substructure at the 6-position, the central ether bond can be replaced by a methylene group without loss of activity. The optimum substituent on the terminal phenyl ring was 3-trifluoromethyl. The compounds showed a strong Hill reaction inhibition, but unfortunately showed poor selectivity between weeds and crops.

  DOI：

  10.1002/(sici)1096-9063(199606)47:2<103::aid-ps396>3.0.co;2-z
• 作为产物：
  描述：

  sodium methylate 、 3,5-二氯-2,4,6-三氟吡啶 以 甲醇 为溶剂， 反应 1.0h， 以85.2%的产率得到3,5-dichloro-2,4-dimethoxy-6-fluoropyridine
  参考文献：
  名称：

  Dimethoxypyrimidines as Novel Herbicides. Part 1. Synthesis and Herbicidal Activity of Dimethoxyphenoxyphenoxypyrimidines and Analogues

  摘要：

  A number of 6-(4-phenoxyphenoxy)pyrimidines and triazines were synthesized and their herbicidal activity was measured. Compounds with the methoxy groups at the 2- and 4-positions on the pyrimidine and triazine rings exhibited high herbicidal activity. Introduction of a substituent into the 5-position of the pyrimidine ring diminished the activity. In the phenoxyphenoxy substructure at the 6-position, the central ether bond can be replaced by a methylene group without loss of activity. The optimum substituent on the terminal phenyl ring was 3-trifluoromethyl. The compounds showed a strong Hill reaction inhibition, but unfortunately showed poor selectivity between weeds and crops.

  DOI：

  10.1002/(sici)1096-9063(199606)47:2<103::aid-ps396>3.0.co;2-z

文献信息

• Polyhalogenated heterocyclic compounds
  作者：Richard D. Chambers、Ali Khalil、Christopher B. Murray、Graham Sandford、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.jfluchem.2005.01.018

  日期：2005.7

  Model studies show that displacement of fluorine, rather than chlorine, occurs upon reaction of 3,5-dichloro-2,4,6-trifluoropyridine with sodium methoxide and phenoxide. Subsequent hydro-dechlorination can be achieved by reaction with lithium aluminium hydride whereas reaction of sodium in iso-propanol leads to formation of the tri-iso-propoxy pyridine derivative, via nucleophilic substitution of the

  模型研究表明，当3,5-二氯-2,4,6-三氟吡啶与甲醇钠和酚盐反应时，会发生氟而不是氯的置换。随后的加氢脱氯化氢可通过与氢化铝锂反应来实现，而钠在异丙醇中的反应则是通过甲氧基的亲核取代而不是脱氯产物形成三异丙氧基吡啶衍生物。大环化合物可以通过适当的双官能氧亲核试剂与3,5-二氯-2,4,6-三氟吡啶的反应合成，其中一种通过X射线晶体学表征。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.5, 4, page 115 - 148
  作者：

  DOI：——

  日期：——
• Chambers, R. D.; Hutchinson, J.; Musgrave, W. K. R., Journal of the Chemical Society
  作者：Chambers, R. D.、Hutchinson, J.、Musgrave, W. K. R.

  DOI：——

  日期：——
• GB1107882
  申请人：——

  公开号：——

  公开（公告）日：——