4-(4-ethoxy-phenyl)-2H-phthalazin-1-one

• 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-ethoxy-phenyl)-2H-phthalazin-1-one
• 英文别名: 4-(4-ethoxyphenyl)-2H-phthalazin-1-one
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: ULZIWUNVIQPQMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-2-triethylsilylacetylene 、 4-(4-ethoxy-phenyl)-2H-phthalazin-1-one 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以76%的产率得到4-(4-ethoxy-2-triethylsilanylethynyl-phenyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  铑（III）通过C-H键活化催化4-芳基酞菁-1（2H）-1骨架的炔基化

  摘要：

  开发了铑（III）催化的4-芳基酞嗪-1（2 H）-one的选择性C H键单/双炔基化。银盐AgSbF 6被证明在促进双炔基化反应中起着至关重要的作用。此外，6-芳基哒嗪-3（2 H）-one支架分别适用于选择性单炔基化和顺序双炔基化。当前的炔基化策略简单，有效，并且在空气气氛下具有高的官能团耐受性和广泛的底物范围。

  DOI：

  10.1002/ejoc.201901731
• 作为产物：
  描述：

  苯乙醚 在 三氯化铝 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-(4-ethoxy-phenyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones

  摘要：

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

  DOI：

  10.1021/jm00077a008

文献信息

• Late-stage functionalization of 4-arylphthalazin-1(2H)-ones by a regioselective iridium-catalyzed C-H bond amidation reaction
  作者：Huimin Li、Wenqing Lan、Ruohan Li、Jianghua Li、Junmin Chen

  DOI：10.24820/ark.5550190.p012.050

  日期：——
• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a008

  日期：1993.12

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.
• Rhodium(III)-Catalyzed Alkynylation of 4-Arylphthalazin-1(2<i>H</i> )-one Scaffolds via C-H Bond Activation
  作者：Xuxin Du、Hongcen Hou、Yongli Zhao、Shouri Sheng、Junmin Chen

  DOI：10.1002/ejoc.201901731

  日期：2020.3.8

  Rhodium(III)‐catalyzed selective C–H bond mono‐/bialkynylation of 4‐aryl phthalazin‐1(2H)‐one was developed. The silver salt AgSbF6 are demonstrated to play a vital role in promoting the bialkynylation reactions. Additionally, 6‐aryl pyridazin‐3(2H)‐one scaffold is amenable to the selective monoalkynylation and sequential bialkynylation, respectively. The present alkynylation strategy is simple, efficient

  开发了铑（III）催化的4-芳基酞嗪-1（2 H）-one的选择性C H键单/双炔基化。银盐AgSbF 6被证明在促进双炔基化反应中起着至关重要的作用。此外，6-芳基哒嗪-3（2 H）-one支架分别适用于选择性单炔基化和顺序双炔基化。当前的炔基化策略简单，有效，并且在空气气氛下具有高的官能团耐受性和广泛的底物范围。