4-(4-chlorophenyl)-3-phenyl-1H-pyridazin-6-one | 351416-13-2

• 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-(4-chlorophenyl)-3-phenyl-1H-pyridazin-6-one
• CAS: 351416-13-2
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: MFSFHFRHJIURPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-3-phenyl-1H-pyridazin-6-one 在 三氯氧磷 作用下， 反应 3.0h， 以83%的产率得到6-Chloro-4-(4-chloro-phenyl)-3-phenyl-pyridazine
  参考文献：
  名称：

  Mono- and Di-substituted 5,6-Diphenyl-3-alkylaminopyridazines Active as ACAT Inhibitors

  摘要：

  A series of mono- or di-para-substituted 5,6-diphenyl-3-alkylaminopyridazines were synthesized and their inhibitory activity against acylCoA:cholesterol acyltransferase (ACAT) was tested on the enzyme prepared from rat liver microsomes. The compound which combines a chlorine atom on the 6-phenyl ring and a n-hexylamino chain showed a significant enhancement of activity with respect to the unsubstituted derivative. Attempts to correlate the activity of the compounds to their structural features, also through theoretical calculations, are reported.

  DOI：

  10.3987/com-01-9351
• 作为产物：
  描述：

  2-(4-氯苯基)-1-苯乙酮 在 sodium hydroxide 、 sodium hydride 、 一水合肼 、 sodium 3-nitrobenzenesulfonate 作用下， 以 sodium hydroxide 、 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 6.0h， 生成 4-(4-chlorophenyl)-3-phenyl-1H-pyridazin-6-one
  参考文献：
  名称：

  Mono- and Di-substituted 5,6-Diphenyl-3-alkylaminopyridazines Active as ACAT Inhibitors

  摘要：

  A series of mono- or di-para-substituted 5,6-diphenyl-3-alkylaminopyridazines were synthesized and their inhibitory activity against acylCoA:cholesterol acyltransferase (ACAT) was tested on the enzyme prepared from rat liver microsomes. The compound which combines a chlorine atom on the 6-phenyl ring and a n-hexylamino chain showed a significant enhancement of activity with respect to the unsubstituted derivative. Attempts to correlate the activity of the compounds to their structural features, also through theoretical calculations, are reported.

  DOI：

  10.3987/com-01-9351

文献信息

• Pyridazines. Part 26: Efficient and Regioselective Pd-Catalysed Arylation of 4-Bromo-6-chloro-3-phenylpyridazine
  作者：Eddy Sotelo、Enrique Raviña

  DOI：10.1055/s-2002-19761

  日期：——

  The regioselective arylation at position 4 of 4-bromo-6-chloro-3-phenylpyridazine has been performed using a Suzuki cross-coupling reaction. This route allows access to a wide-ranging series of pharmacologically useful pyridazine derivatives and confirms the usefulness of chloropyridazines as a masking group for the carbonyl moiety in cross-coupling reactions involving 5-bromo-3(2H)-pyridazinones.

  4-bromo-6-chloro-3-phenylpyridazine 4-bromo-6-chloro-3-phenylpyridazine 的区域选择性芳基化已经使用 Suzuki 交叉偶联反应进行。该路线允许获得一系列广泛的药理学有用的哒嗪衍生物，并证实了氯哒嗪在涉及 5-溴-3(2H)-哒嗪酮的交叉偶联反应中作为羰基部分的掩蔽基团的有用性。
• Pyridazines. Part 35:Traceless Solid PhaseSynthesis of 4,5- and 5,6-Diaryl-3(2<i>H</i>)-pyridazinones
  作者：Enrique Raviña、Eddy Sotelo

  DOI：10.1055/s-2003-39882

  日期：——

  A new method for the traceless solid phase synthesis of 3(2H)-pyridazinones has been developed employing dihydropyran-functionalized resin. The procedure has permitted the preparation of several diarylpyridazinones through a Suzuki cross-coupling reaction and cleavage conditions that promoted a retro-ene fragmentation.

  利用二氢吡喃功能化树脂开发了一种无痕固相合成 3(2H)-哒嗪酮的新方法。该方法通过铃木交叉偶联反应和促进逆烯碎片的裂解条件，制备出了多种二芳基哒嗪酮。
• Pyridazines Part XXIII: Efficient Arylation at Position 5 of the 6-Phenyl-(2H)-pyridazin-3-one System Using a Suzuki Cross-Coupling Reaction
  作者：Alberto Coelho、Eddy Sotelo、Isabel Estévez、Enrique Raviña

  DOI：10.1055/s-2001-13409

  日期：——

  A highly efficient procedure for introducing aryl or heteroaryl rings at position 5 of the 6-phenyl-(2H)-pyridazin-3-one system using a Suzuki cross-coupling reaction has been developed in the search for new platelet aggregation inhibitors.

  为了寻找新的血小板聚集抑制剂，我们开发了一种高效的程序，利用铃木交叉偶联反应在 6-苯基-(2H)-哒嗪-3-酮体系的第 5 位引入芳基或杂芳基环。
• Pyridazines. Part 30:Palladium-Catalysed Synthesis of 5-Substituted 6-Phenyl-3(2<i>H</i>)-pyridazinones Asissted by a Retro-Ene Transformation
  作者：Eddy Sotelo、Alberto Coelho、Enrique Raviña

  DOI：10.1055/s-2002-35567

  日期：——

  The efficient one-pot functionalization, through palladium-catalysed reactions, of position 5 of the 6-phenyl-3(2H)-pyridazinone system has been performed using a retro-ene-assisted fragmentation. This route allows accessthrough a short synthetic sequence to several pharmacologically useful 3(2H)-pyridazinones.

  通过钯催化反应，6-苯基-3(2H)-哒嗪酮系统的第 5 位的有效一锅官能化已使用逆烯辅助碎裂进行。该路线允许通过短合成序列获得几种药理学上有用的 3(2H)-哒嗪酮。
• Pyridazines. Part 36: Synthesis and antiplatelet activity of 5-substituted-6-phenyl-3(2H)-pyridazinones
  作者：Alberto Coelho、Eddy Sotelo、Nuria Fraiz、Matilde Yáñez、Reyes Laguna、Ernesto Cano、Enrique Raviña

  DOI：10.1016/j.bmcl.2003.11.009

  日期：2004.1

  A convenient and efficient palladium-catalysed retro-ene-assisted method has been developed to prepare a series of 5-substituted-6-phenyl-3(2H)-pyridazinones as potential antiplatelet drugs. The most active compounds were those that contain a 3-phenyl-3-oxo-propenyl fragment or a phenylthio group at position 5 of the heterocyclic ring. (C) 2003 Elsevier Ltd. All rights reserved.