4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one | 75643-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one
• 英文别名: 4-acetyl-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one；5-acetyl-3,4-bis(4-chlorophenyl)-6(1H)-pyridazinone；5-acetyl-3,4-bis(4-chlorophenyl)-1H-pyridazin-6-one
• CAS: 75643-31-1
• 化学式: C₁₈H₁₂Cl₂N₂O₂
• 分子量: 359.211
• InChiKey: VEKTYHRMOKSDMU-UHFFFAOYSA-N

物化性质

• 熔点：
  269-271 °C(Solv: acetonitrile (75-05-8))
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one 在 吡啶 、 氢氧化钾 、 sodium iodide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 43.5h， 生成 4-acetyl-5,6-bis(4-chlorophenyl)-2-(2-iodoethyl)-2H-pyridazin-3-one
  参考文献：
  名称：

  Antihypertensive 5,6-diarylpyridazin-3-ones

  摘要：

  The synthesis of a series of 5,6-diarylpyridazinones is described. Some members of this series display an antihypertensive effect in both the spontaneously hypertensive rat (SHR) model and the deoxycorticosteroid (DOCA) model of hypertension. The most potent compounds in the series have halogen substituents on the 5,6-diphenyl rings, a beta-substituted alkyl group at the 2 position of the ring, and acetyl or cyano substituent at the 4 position.

  DOI：

  10.1021/jm00186a021
• 作为产物：
  描述：

  4-acetyl-5,6-bis(4-chlorophenyl)-3-methoxypyridazine 在 氢碘酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one
  参考文献：
  名称：

  哒嗪的金属化和交叉偶联制备5,6-二芳基哒嗪-3-酮的新途径

  摘要：

  从3,6-二氯哒嗪开始，描述了一种抗高血压的5,6-二芳基哒嗪-3-酮的新途径。该途径包括区域选择性金属化，随后是三甲基甲硅烷基部分的取代。通过另一种金属化引入的碘允许芳基硼酸的交叉偶联。然后将6-甲氧基裂解以得到哒嗪酮。

  DOI：

  10.1002/jhet.5570320364

文献信息

• Antihypertensive pyridazin(2H)-3-ones
  申请人：Diamond Shamrock Corporation

  公开号：US04238490A1

  公开（公告）日：1980-12-09

  Compounds of the formula ##STR1## are useful antihypertensive agents.

  式为##STR1##的化合物是有用的降压剂。
• Isolation and Identification of Impurities in 4-Acetyl-2-(2′-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one, an Antihypertensive Agent
  作者：Larry J. Powersx、David J. Eckert、Lane Gehrlein

  DOI：10.1002/jps.2600700419

  日期：1981.4

  Three trace impurities found in 4-acetyl-2-(2'-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one (II), a novel antihypertensive agent, were isolated by a combination of low-pressure liquid chromatography and preparative TLC. These impurities were identified as the formate ester of II, a pyridazinone having a 2-methyl rather than the 2'-hydroxyethyl substituent, and a bis(pyridazinonyl)methane

  通过组合分离在4-乙酰基-2-（2'-羟乙基）-5,6-双（4-氯苯基）-2H-哒嗪-3-酮（II）中发现的三种微量杂质液相色谱和制备薄层色谱的制备 这些杂质被鉴定为II的甲酸酯，具有2-甲基而不是2'-羟乙基取代基的哒嗪酮和双（吡啶并壬基）甲烷类似物。此外，通过高性能检测到了4-乙酰基5,6-双（4-氯苯基）-2H-哒嗪-3-酮（I）与碳酸亚乙酯的O-烷基化而不是N-烷基化的产物液相色谱。将这四种杂质的生物活性与II进行了比较。
• Quinoline catalyzed synthesis of pyridazinone pharmaceutical
  申请人：Diamond Shamrock Corporation

  公开号：US04281125A1

  公开（公告）日：1981-07-28

  Valuable pyridazinone intermediates to pharmaceutically useful compounds can be prepared in surprisingly high yields by the quinoline catalyzed reaction of the corresponding monohydrazone with an appropriately substituted acetic acid ester. In an especially preferred embodiment, p,p'-dichlorobenzil monohydrazone and methyl acetoacetate are reacted in a xylene solvent in the presence of quinoline to afford 4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one, which can then be reacted with ethylene carbonate in the presence of potassium carbonate to afford the antihypertensive agent, 4-acetyl-5,6-bis(p-chlorophenyl)-2-(2'-hydroxyethyl)-2H-pyridazin-3-one.

  通过喹啉催化反应相应的单肼与适当取代的乙酸酯反应，可以制备出具有药用价值的吡啶并咪唑酮中间体，收率惊人地高。在特别优选的实施方式中，p,p'-二氯苯甲酰单肼和乙酰乙酸甲酯在二甲苯溶剂中在喹啉的存在下反应，得到4-乙酰基-5,6-双(对氯苯基)-2H-吡啶并咪唑酮，然后在碳酸钾的存在下与乙二醇碳酸酯反应，得到降压药物4-乙酰基-5,6-双(对氯苯基)-2-(2'-羟乙基)-2H-吡啶并咪唑酮。
• Synthesis of pyridazinone pharmaceutical intermediates using diketene
  申请人：Diamond Shamrock Corporation

  公开号：US04286091A1

  公开（公告）日：1981-08-25

  Valuable pyridazinone intermediates to pharmaceutically useful compounds can be prepared in surprisingly high yields by the reaction of the corresponding monohydrazone with diketene, preferably in the presence of a basic catalyst. In an especially preferred embodiment, p,p'-dichlorobenzil monohydrazone and diketene are reacted in a xylene solvent in the presence of triethylamine to afford 4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one, which can then be reacted with ethylene carbonate in the presence of potassium carbonate to afford the antihypertensive agent, 4-acetyl-5,6-bis(p-chlorophenyl)-2-(2'-hydroxyethyl)-2H-pyridazine-3-one.

  通过将相应的单酰肼与二酮在碱催化剂的存在下反应，可以以惊人的高产率制备用于制药的有用化合物的有价值的吡啶并酮中间体。在一种特别优选的实施方式中，p，p'-二氯苯甲酰单酰肼和二酮在三乙胺存在下的二甲苯溶剂中反应，得到4-乙酰基-5,6-双(对氯苯基)-2H-吡啶并[3,2-c][1,2,4]噻唑-3-酮，然后在碳酸钾存在下与碳酸乙烯酯反应，得到降压剂4-乙酰基-5,6-双(对氯苯基)-2-(2'-羟乙基)-2H-吡啶并[3,2-c][1,2,4]噻唑-3-酮。
• Pyridazin (2H)-3-ones, process for their preparation and their use in antihypertensive agents
  申请人：DIAMOND SHAMROCK CORPORATION

  公开号：EP0018063A1

  公开（公告）日：1980-10-29

  Substituted keto-pyridazine compounds of the formula where R, and R7 are substituents selected from atoms and groups as listed in the disclosure and X and Y denote the same or different optional substituents also selected as listed in the disclosure, are new compounds which are useful antihypertensive agents. The methods of preparation and properties of examples of the compounds are given, together with their use as antihypertensive agents.

  式中的取代酮哒嗪化合物 其中 R 和 R7 是选自公开文献中所列原子和基团的取代基，X 和 Y 表示相同或不同的任选取代基，也选自公开文献中所列基团。本文给出了这些化合物的制备方法和性质实例，以及它们作为降压药的用途。