4-(tert-butylamino)-2-phenylphthalazin-1(2H)-one | 1346229-14-8

• 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-(tert-butylamino)-2-phenylphthalazin-1(2H)-one
• 英文别名: 4-(Tert-butylamino)-2-phenylphthalazin-1-one；4-(tert-butylamino)-2-phenylphthalazin-1-one
• CAS: 1346229-14-8
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: ZWBVGAFUQWRDHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-butylamino)-2-phenylphthalazin-1(2H)-one 在 tetrafluoroboric acid 作用下， 以 水 、 正丁醇 为溶剂， 反应 0.33h， 生成 4-amino-2-phenylphthalazin-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
• 作为产物：
  描述：

  异氰酸叔丁酯 、 邻溴苯甲酸甲酯 、 苯肼 在 palladium diacetate 、 二异丙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以63%的产率得到4-(tert-butylamino)-2-phenylphthalazin-1(2H)-one
  参考文献：
  名称：

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

  摘要：

  Palladium-catalyzed cross-coupling of a wide range of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion followed by lactamization efficiently affords 4-aminophthalazin-1(2H)-ones that are difficult to obtain regioselectively by classical methods.

  DOI：

  10.1021/ol202784d

文献信息

• Palladium-Catalyzed Synthesis of 4-Aminophthalazin-1(2<i>H</i>)-ones by Isocyanide Insertion
  作者：Tjøstil Vlaar、Eelco Ruijter、Anass Znabet、Elwin Janssen、Frans J. J. de Kanter、Bert U. W. Maes、Romano V. A. Orru

  DOI：10.1021/ol202784d

  日期：2011.12.16

  Palladium-catalyzed cross-coupling of a wide range of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion followed by lactamization efficiently affords 4-aminophthalazin-1(2H)-ones that are difficult to obtain regioselectively by classical methods.
• 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.