6-溴-4,5-氯-3(2H)-哒嗪 | 933041-14-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 哒嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-溴-4,5-氯-3(2H)-哒嗪
• 中文别名: 6-溴-4,5-二氯-3(2H)-吡嗪酮
• 英文名称: 6-bromo-4,5-dichloropyridazin-3(2H)-one
• 英文别名: 3-bromo-4,5-dichloro-1H-pyridazin-6-one；6-Bromo-4,5-dichloro-3(2H)-pyridazinone
• CAS: 933041-14-6
• 化学式: C₄HBrCl₂N₂O
• 分子量: 243.875
• InChiKey: CIXBFXGEDMRWSN-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

用途

6-溴-4,5-氯-3(2H)-哒嗪是一种有用的有机合成研究化学品，广泛应用于其他化学过程。

反应信息

• 作为反应物：
  描述：

  6-溴-4,5-氯-3(2H)-哒嗪 、 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以25 g的产率得到6-bromo-4,5-dichloro-2-((2-methyl-6-(trifluoromethyl)-pyridin-3-yl)methyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Reductions in log P Improved Protein Binding and Clearance Predictions Enabling the Prospective Design of Cannabinoid Receptor (CB1) Antagonists with Desired Pharmacokinetic Properties

  摘要：

  Several strategies have been employed to reduce the long in vivo half-life of our lead CB1 antagonist, triazolopyridazinone 3, to differentiate the pharmacokinetic profile versus the lead clinical compounds. An in vitro and in vivo clearance data set revealed a lack of correlation; however, when compounds with <5% free fraction were excluded, a more predictable correlation was observed. Compounds with log P between 3 and 4 were likely to have significant free fraction, so we designed compounds in this range to give more predictable clearance values. This strategy produced compounds with desirable in vivo half-lives, ultimately leading to the discovery of compound 46. The progression of compound 46 was halted due to the contemporaneous marketing and clinical withdrawal of other centrally acting CB1 antagonists; however, the design strategy successfully delivered a potent CB1 antagonist with the desired pharmacokinetic properties and a clean off-target profile.

  DOI：

  10.1021/jm4010835
• 作为产物：
  描述：

  4,5-二氯-3-羟基哒嗪 在 溴 作用下， 以 水 为溶剂， 反应 48.0h， 以57%的产率得到6-溴-4,5-氯-3(2H)-哒嗪
  参考文献：
  名称：

  Studies on Improved Synthesis of 2'-Deoxyribonucleosides of Pyridazine Derivatives

  摘要：

  通过在丙酮中将相应的卤代哒嗪衍生物的钾盐或DBU盐进行糖基化，制备了一系列卤代哒嗪衍生的2'-脱氧核苷。反应主要产生β-异构体，可通过简单结晶或柱层析纯化。在研究的哒嗪和脱氧核苷中，只有4-溴-6-氯哒嗪-3-酮和6-氯-2-(2'-脱氧核糖呋喃糖基)哒嗪-3-酮显示出对CK2激酶的适度抑制作用。

  DOI：

  10.1135/cccc20060889

文献信息

• [EN] PYRIDAZINONES DERIVATIVES AS HERBICIDAL COMPOUNDS<br/>[FR] DÉRIVÉS DE PYRIDAZINONES EN TANT QUE COMPOSÉS HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2015052095A1

  公开（公告）日：2015-04-16

  The present invention relates to novel herbicidal pyridazinones of formula (I), processes and intermediates used for their preparation, as well as herbicidal compositions comprising such pyridazinones. The invention further extends to the use of such compounds and compositions in controlling undesirable plant and in particular the use in controlling weeds, such as broadleaved dicotyledonous weeds, in crops of useful plants.

  本发明涉及新型杂环醚嘧啶酮的化学式(I)，用于其制备的工艺和中间体，以及包含这些杂环醚嘧啶酮的除草剂组合物。该发明进一步涉及在控制不良植物，特别是在控制杂草（如双子叶宽叶杂草）在有用植物作物中的使用中，使用这些化合物和组合物。
• PYRIDAZINONE HERBICIDAL COMPOUNDS
  申请人：Syngenta Limited

  公开号：US20150031540A1

  公开（公告）日：2015-01-29

  The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein X 1 , R 1 , R 2 , R 3 , R 5 , G and n are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and to their use for controlling weeds, in particular in crops of useful plants.

  本发明涉及Formula（I）的化合物，或者该化合物的农学上可接受的盐，其中X1、R1、R2、R3、R5、G和n如本文中所定义。该发明还涉及包含Formula（I）化合物的除草剂组合物，并且用于控制杂草，特别是在有用植物作物中的使用。
• [EN] PYRIDAZINONE HERBICIDAL COMPOUNDS<br/>[FR] COMPOSÉS HERBICIDES PYRIDAZINONE
  申请人：SYNGENTA LTD

  公开号：WO2013160126A1

  公开（公告）日：2013-10-31

  The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein X1, R1, R2, R3, R5, G and n are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and to their use for controlling weeds, in particular in crops of useful plants.

  本发明涉及式（I）化合物，或者该化合物的农业上可接受的盐，其中X1、R1、R2、R3、R5、G和n的定义如本文所述。该发明还涉及含有式（I）化合物的除草剂组合物，并且用于控制杂草，特别是在有用植物作物中的使用。
• [EN] HERBICIDAL PYRIDAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS HERBICIDES DE PYRIDAZINONE
  申请人：DU PONT

  公开号：WO2009086041A1

  公开（公告）日：2009-07-09

  Disclosed are compounds of Formula (1), N-oxides, and salts thereof, wherein W1 is O or S, and R1, R2, R3, G and J are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

  揭示了Formula (1)的化合物、N-氧化物及其盐，其中W1是O或S，R1、R2、R3、G和J的定义如披露所述。还揭示了含有Formula (1)化合物的组合物，以及用于控制不受欢迎的植被的方法，包括将不受欢迎的植被或其环境与本发明的化合物或组合物的有效量接触。
• Studies on Improved Synthesis of 2'-Deoxyribonucleosides of Pyridazine Derivatives
  作者：Zygmunt Kazimierczuk、Jarosław Kamiński、Flavio Meggio

  DOI：10.1135/cccc20060889

  日期：——

  A number of 2'-deoxyribonucleosides of halogenated pyridazine derivatives were prepared by glycosylation of their respective potassium or DBU salts in acetone. The reaction yielded predominatly β-anomers that could be purified by simple crystallization or column chromatography. Of the studied pyridazines and deoxynucleosides, only 4-bromo-6-chloropyridazin-3-one and 6-chloro-2-(2'-deoxyribofuranosyl)pyridazin-3-one showed modest inhibition of CK2 kinase.

  通过在丙酮中将相应的卤代哒嗪衍生物的钾盐或DBU盐进行糖基化，制备了一系列卤代哒嗪衍生的2'-脱氧核苷。反应主要产生β-异构体，可通过简单结晶或柱层析纯化。在研究的哒嗪和脱氧核苷中，只有4-溴-6-氯哒嗪-3-酮和6-氯-2-(2'-脱氧核糖呋喃糖基)哒嗪-3-酮显示出对CK2激酶的适度抑制作用。