2-phenyl-1,2-dihydrophthalazine | 128174-77-6

• 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: 2-phenyl-1,2-dihydrophthalazine
• 英文别名: Phthalazine, 1,2-dihydro-2-phenyl-；2-phenyl-1H-phthalazine
• CAS: 128174-77-6
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: RSSGKNIPDNJYDI-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：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氰基溴苄 在 iron(III) chloride 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 28.42h， 生成 2-phenyl-1,2-dihydrophthalazine
  参考文献：
  名称：

  Synthesis of 2-Aryl-1,2-dihydrophthalazines via Reaction of 2-(Bromomethyl)benzaldehydes with Arylhydrazines

  摘要：

  The reaction of 2-(bromomethyl)benzaldehydes with arylhydrazines employing K2CO3 as a base and FeCl3 as a catalyst in CH3CN at 100 degrees C delivers 2-aryl-1,2-dihydrophthalazines with yields ranging from 60 to 91%. The transformation is considered to proceed as an intermolecular condensation/intramolecular nucleophilic substitution.

  DOI：

  10.1021/jo302491x

文献信息

• Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: syntheses of pyrazole, pyrazolidine and phthalazine derivatives
  作者：Yuhong Ju、Rajender S. Varma

  DOI：10.1016/j.tetlet.2005.07.018

  日期：2005.9

  Direct syntheses of 4,5-dihydro-pyrazole, pyrazolidine, and 1,2-dihydro-phthalazine derivatives via double-alkylation of hydrazines by alkyl dihalides or ditosylates were accomplished in aqueous media under microwave irradiation conditions; the environmentally friendlier chemical transformation occurred in a single step and eliminated the use of expensive metal catalysts in building two C–N bonds.

  在微波辐射条件下，在含水介质中，通过烷基二卤化物或二甲苯磺酸盐对肼的双烷基化反应，直接合成4，5-二氢吡唑，吡唑烷和1，2-二氢邻苯二甲酰肼衍生物。有利于环境的化学转化过程一步完成，消除了使用昂贵的金属催化剂来构建两个C–N键的过程。
• Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides:  Microwave-Assisted Syntheses of <i>N</i>-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives
  作者：Yuhong Ju、Rajender S. Varma

  DOI：10.1021/jo051878h

  日期：2006.1.1

  The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple C C and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-diliydro-1H-isoindoles. 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.
• Butler, Richard N.; Gillan, Ann M.; Lysaght, Fiona A., Journal of the Chemical Society. Perkin transactions I, 1990, p. 555 - 564
  作者：Butler, Richard N.、Gillan, Ann M.、Lysaght, Fiona A.、McArdle, Patrick、Cunningham, D.

  DOI：——

  日期：——
• Synthesis of 2-Aryl-1,2-dihydrophthalazines via Reaction of 2-(Bromomethyl)benzaldehydes with Arylhydrazines
  作者：Nayyef Aljaar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/jo302491x

  日期：2013.2.1

  The reaction of 2-(bromomethyl)benzaldehydes with arylhydrazines employing K2CO3 as a base and FeCl3 as a catalyst in CH3CN at 100 degrees C delivers 2-aryl-1,2-dihydrophthalazines with yields ranging from 60 to 91%. The transformation is considered to proceed as an intermolecular condensation/intramolecular nucleophilic substitution.