4-amino-2-(4-methoxyphenyl)phthalazin-1(2H)-one | 1415648-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-amino-2-(4-methoxyphenyl)phthalazin-1(2H)-one
• 英文别名: 2-(4-methoxyphenyl)-4-aminophthalazin-1(2H)-one；4-Amino-2-(4-methoxyphenyl)phthalazin-1-one；4-amino-2-(4-methoxyphenyl)phthalazin-1-one
• CAS: 1415648-00-8
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: LXCDKMQCDPJIAL-UHFFFAOYSA-N

物化性质

• 沸点：
  486.1±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(三氟甲基磺酰氧基)苯甲酸甲酯 在 copper(l) iodide 、 tetrafluoroboric acid 、 trans-1,2-Diaminocyclohexane 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 24.41h， 生成 4-amino-2-(4-methoxyphenyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  Multicomponent Synthesis of 4-Aminophthalazin-1(2H)-ones by Palladium-Catalyzed Isocyanide Insertion

  摘要：

  4-Aminophthalazin-1(2H)-ones (APOs) are underexplored heterocyclic compounds with promising and diverse biological activities. The classical synthesis of these compounds is tedious and does not allow the regioselective introduction of substituents. Here, we present our full studies on the Pd-catalyzed cross-coupling of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion allowing straightforward access to diversely substituted APOs. We illustrate the advantages of this method compared to other approaches and describe solutions for the limitations we encountered. In addition, we have developed efficient diversifications of this heterocyclic scaffold that allow access to more diverse APOs as well as novel heterocyclic scaffolds.

  DOI：

  10.1021/jo401131p

文献信息

• Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones
  作者：Gani Koza、Selbi Keskin、Merve Sinem Özer、Betül Cengiz、Ertan Şahin、Metin Balci

  DOI：10.1016/j.tet.2012.10.010

  日期：2013.1

  of the ketoesters with hydrazine provided the hydrazone derivatives. An intramolecular cyclization in the presence of thionyl chloride formed a fused pyridazinone skeleton. Hydrolysis of the remaining ester groups and transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the isocyanates. Reaction of the isocyanates with methanol and water produced urethane

  我们在此报告新型化合物的合成，7-氨基呋喃-和7-氨基噻吩并[2,3 - d ]哒嗪-4（5 H）-one和4-氨基酞嗪-1（2 H）-由2-（2-甲氧基-2-氧代乙基）呋喃甲酸甲酯和噻吩-3-羧酸甲酯和2-（2-甲氧基-2-氧代乙基）苯甲酸甲酯开始。直接连接到芳环的酯官能团被区域特异性地转化成酸，而亚甲基被氧化成相应的酮酯。酮酯与肼的反应提供了derivatives衍生物。在亚硫酰氯存在下的分子内环化形成稠合的哒嗪酮骨架。其余酯基的水解和酸官能度向酰基叠氮化物的转化，然后Curtius重排，得到异氰酸酯。异氰酸酯与甲醇和水的反应分别生成氨基甲酸酯和氨基哒嗪酮衍生物。
• Multicomponent Synthesis of 4-Aminophthalazin-1(2<i>H</i>)-ones by Palladium-Catalyzed Isocyanide Insertion
  作者：Tjøstil Vlaar、Pieter Mampuys、Madeleine Helliwell、Bert U. W. Maes、Romano V. A. Orru、Eelco Ruijter

  DOI：10.1021/jo401131p

  日期：2013.7.5

  4-Aminophthalazin-1(2H)-ones (APOs) are underexplored heterocyclic compounds with promising and diverse biological activities. The classical synthesis of these compounds is tedious and does not allow the regioselective introduction of substituents. Here, we present our full studies on the Pd-catalyzed cross-coupling of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion allowing straightforward access to diversely substituted APOs. We illustrate the advantages of this method compared to other approaches and describe solutions for the limitations we encountered. In addition, we have developed efficient diversifications of this heterocyclic scaffold that allow access to more diverse APOs as well as novel heterocyclic scaffolds.