2,4-dichloro-6-hydrazinopyridine | 837365-03-4

• 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: 2,4-dichloro-6-hydrazinopyridine
• 英文别名: (4,6-dichloropyridin-2-yl)hydrazine
• CAS: 837365-03-4
• 化学式: C₅H₅Cl₂N₃
• mdl: MFCD09031041
• 分子量: 178.021
• InChiKey: GYMRGLRMUMWBBA-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  225.2±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-hydrazinopyridine 在 copper(II) sulfate 作用下， 生成 2,4-二氯吡啶
  参考文献：
  名称：

  Rerouting Nucleophilic Substitution from the 4-Position to the 2- or 6-Position of 2,4-Dihalopyridines and 2,4,6-Trihalopyridines: The Solution to a Long-Standing Problem

  摘要：

  2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, the halogen at the 6-(2-)position is displaced selectively. This synthetically valuable regiocontrol can also be realized with other halopyridines such as 2,4-dichloro- and 2,4,6-trichloropyridine.

  DOI：

  10.1021/ol047826g
• 作为产物：
  描述：

  2,4,6-三氯吡啶 在 正丁基锂 、 四丁基氟化铵 、 一水合肼 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.75h， 生成 2,4-dichloro-6-hydrazinopyridine
  参考文献：
  名称：

  Regiochemically Flexible Substitutions of Di-, Tri-, and Tetrahalopyridines:  The Trialkylsilyl Trick

  摘要：

  2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.

  DOI：

  10.1021/jo047962z

文献信息

• Rerouting Nucleophilic Substitution from the 4-Position to the 2- or 6-Position of 2,4-Dihalopyridines and 2,4,6-Trihalopyridines: The Solution to a Long-Standing Problem
  作者：Manfred Schlosser、Thierry Rausis、Carla Bobbio

  DOI：10.1021/ol047826g

  日期：2005.1.1

  2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, the halogen at the 6-(2-)position is displaced selectively. This synthetically valuable regiocontrol can also be realized with other halopyridines such as 2,4-dichloro- and 2,4,6-trichloropyridine.
• [EN] 6-AZA-TETRAHYDRO-γ-CARBOLINE DERIVATIVE AND MEDICINAL USE OF SAME<br/>[FR] DÉRIVÉ DE 6-AZA-TÉTRAHYDRO-γ-CARBOLINE ET SON UTILISATION MÉDICALE<br/>[JA] ６－アザ－テトラヒドロ－γ－カルボリン誘導体及びその医薬用途
  申请人：TORAY INDUSTRIES

  公开号：WO2016152759A1

  公开（公告）日：2016-09-29

  　本発明は、５－ＨＴ２Ｃ受容体作動活性を有する、腹圧性尿失禁の治療剤又は予防剤として有用な化合物を提供することを目的としている。本発明は、下記の化学式に代表される６－アザ－テトラヒドロ－γ－カルボリン誘導体又はその薬学的に許容される酸付加塩を提供する。
• 双環式ピリジン誘導体およびその塩、並びに、当該誘導体又はその塩を有効成分として含有することを特徴とする有害生物防除剤
  申请人：[en]HOKKO CHEMICAL INDUSTRY CO., LTD.;[ja]北興化学工業株式会社

  公开号：WO2024117205A1

  公开（公告）日：2024-06-06

  本発明は、下記一般式（１）で表される双環式ピリジン誘導体又はその塩、及び、前記双環式ピリジン誘導体又はその塩を有効成分として含有する農園芸用薬剤、殺虫剤等を提供する。前記一般式（１）中、Ｒ１、Ｒ２、Ｚ、及びＡ１～Ａ３は、それぞれ所定の置換基を表し、ｎは０または１を表す。
• Regiochemically Flexible Substitutions of Di-, Tri-, and Tetrahalopyridines:  The Trialkylsilyl Trick
  作者：Manfred Schlosser、Carla Bobbio、Thierry Rausis

  DOI：10.1021/jo047962z

  日期：2005.4.1

  2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.