N-(tert-butyl)-4-chlorophthalazin-1-amine

• 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: N-(tert-butyl)-4-chlorophthalazin-1-amine
• 英文别名: N-tert-butyl-4-chlorophthalazin-1-amine
• 化学式: C₁₂H₁₄ClN₃
• 分子量: 235.716
• InChiKey: TUEJEULNOICWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯苯甲酸甲酯 在 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氯氧磷 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 22.08h， 生成 N-(tert-butyl)-4-chlorophthalazin-1-amine
  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

• 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.