1,4-diethoxyphthalazine | 19064-72-3

• 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: 1,4-diethoxyphthalazine
• 英文别名: 1,4-diethoxy-phthalazine；1,4-Diaethoxy-phthalazin
• CAS: 19064-72-3
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: OOTQDEUWWZEDFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-二氯酞嗪 、 sodium ethanolate 在 sodium 作用下， 以 异丙醇 为溶剂， 以55%的产率得到1,4-diethoxyphthalazine
  参考文献：
  名称：

  摘要：

  Electrochemical reduction in dimethylformamide of unsymmetrical 1-Cl-4-X-phthalazines and symmetrical 1,4-X-2-phthalazines (X = Cl, PhO, MeO, EtO, i-PrO) was studied by voltammetry and electrolysis-ESR. The electron trasfer on 1,4-dichlorophthalazine and unsymmetrical 1-Cl-4-X-phthalazines induces anionoid elimination of Cl and X, pyridazine ring cleavage, and phthalonitrile formation. In this previously unknown process the transfer of two electrons induces cleavage of three sigma bonds and formation of two new pi bonds. The reduction of 1,4-dialkoxy(diaryloxy)phthalazines involves formation of stable radical anions which undergo no heteroring cleavage. Possible mechanisms of the processes studied were discussed. It was assumed that the same mechanism with pyridazine ring cleavage may be realized with other phthalazine derivatives and heteroannelated pyridazines containing readily leaving nucleofuge groups alpha to nitrogens.

  DOI：

  10.1023/a:1013979709884

文献信息

• Phase transfer catalysed reductive acylation of nitrogen-containing heteroaromatics with acetylcobalt tetracarbonyl
  作者：Ming de Wang、Howard Alper

  DOI：10.1016/0022-328x(93)83023-o

  日期：1993.6

  Phase transfer catalyzed reductive ring-cleavage acylation of isoxazoles or isothiazoles with acetylcobalt tetracarbonyl gives N-acylated 1-amino-2-alkene-3-ones or thiones. Under the same conditions phthalazine, quinoline and isoquinoline react with acetylcobalt tetracarbonyl to give N-acylated dimers. The reactivity of several other nitrogen-containing heterocycles was also investigated.
• APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：EP2970257A1

  公开（公告）日：2016-01-20
• [EN] APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES<br/>[FR] AGENTS INDUISANT L'APOPTOSE POUR LE TRAITEMENT DU CANCER ET DE MALADIES IMMUNES ET AUTO-IMMUNES
  申请人：ABBVIE INC

  公开号：WO2014158528A1

  公开（公告）日：2014-10-02

  Disclosed herein are compounds that inhibit the activity of anti-apoptotic Bcl-2 proteins, compositions containing the compounds and methods of treating diseases using the compounds.
• ——
  作者：V. V. Yanilkin、B. I. Buzykin、V. I. Morozov、N. V. Nastapova、N. I. Maksimyuk、R. M. Eliseenkova

  DOI：10.1023/a:1013979709884

  日期：——

  Electrochemical reduction in dimethylformamide of unsymmetrical 1-Cl-4-X-phthalazines and symmetrical 1,4-X-2-phthalazines (X = Cl, PhO, MeO, EtO, i-PrO) was studied by voltammetry and electrolysis-ESR. The electron trasfer on 1,4-dichlorophthalazine and unsymmetrical 1-Cl-4-X-phthalazines induces anionoid elimination of Cl and X, pyridazine ring cleavage, and phthalonitrile formation. In this previously unknown process the transfer of two electrons induces cleavage of three sigma bonds and formation of two new pi bonds. The reduction of 1,4-dialkoxy(diaryloxy)phthalazines involves formation of stable radical anions which undergo no heteroring cleavage. Possible mechanisms of the processes studied were discussed. It was assumed that the same mechanism with pyridazine ring cleavage may be realized with other phthalazine derivatives and heteroannelated pyridazines containing readily leaving nucleofuge groups alpha to nitrogens.