1-phenyl-4-(4′-methylphenyl)phthalazine | 5778-09-6

• 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: 1-phenyl-4-(4′-methylphenyl)phthalazine
• 英文别名: 4-(4-Methyl-phenyl)-1-phenyl-phthalazin；1-phenyl-4-p-tolylphthalazine；1-Phenyl-4-p-tolyl-phthalazin；1-(4-Methylphenyl)-4-phenylphthalazine；1-(4-methylphenyl)-4-phenylphthalazine
• CAS: 5778-09-6
• 化学式: C₂₁H₁₆N₂
• 分子量: 296.371
• InChiKey: IKGBHHWDWOHTJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4'-Methyl-2-benzyl-diphenylketimin 在 氧气 、 copper diacetate 、 肼 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 8.0h， 以119.6 mg的产率得到1-phenyl-4-(4′-methylphenyl)phthalazine
  参考文献：
  名称：

  Copper-Catalyzed Benzylic C−H Oxygenation under an Oxygen Atmosphere via N-H Imines as an Intramolecular Directing Group

  摘要：

  Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.

  DOI：

  10.1021/ol200425c

文献信息

• Facile synthesis of 1-substituted 4-H phthalazine, a versatile scaffold for chemically diverse phthalazines
  作者：Rungsima Hadsarung、Sanit Thongnest、Sittisak Oekchuae、Duangduan Chaiyaveij、Jutatip Boonsombat、Somsak Ruchirawat

  DOI：10.1016/j.tet.2022.132920

  日期：2022.8

  An improved synthetic strategy for 1-substituted 4-H phthalazines using a convenient, three-step reaction sequence under mild conditions is described. The protocol involves condensation of hydrazine hydrate with o-ketobenzaldehydes derived through the Pb(OAc)4 oxidation of the N-acylhydrazones of salicylaldehydes. This pathway is of high practical value since a wide variety of substituted acylhydrazides

  描述了在温和条件下使用方便的三步反应序列改进 1-取代 4-H 酞嗪的合成策略。该协议涉及水合肼与通过水杨醛的N-酰基腙的 Pb(OAc) 4氧化衍生的邻酮苯甲醛的缩合。该途径具有很高的实用价值，因为种类繁多的取代酰肼和水杨醛是N-酰基腙是可商购的。此外，三步序列可以扩大规模，无需中间纯化，以高产率提供广泛的产品。1-苯基 4-H 酞嗪是一种多功能化合物，可提供多种酞嗪类似物，包括血管扩张剂 MY5445。
• Guyot; Vallette, Annales de Chimie (Cachan, France), 1911, vol. <8> 23, p. 376
  作者：Guyot、Vallette

  DOI：——

  日期：——
• Copper-Catalyzed Benzylic C−H Oxygenation under an Oxygen Atmosphere via <i>N</i>-H Imines as an Intramolecular Directing Group
  作者：Line Zhang、Gim Yean Ang、Shunsuke Chiba

  DOI：10.1021/ol200425c

  日期：2011.4.1

  Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.