4-Benzyl-1,4-dihydro-1,3-diphenyl-1,2,4-benzotriazin | 74172-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Benzyl-1,4-dihydro-1,3-diphenyl-1,2,4-benzotriazin
• 英文别名: 4-benzyl-1,3-diphenyl-1,4-dihydrobenzo[e][1,2,4]triazine；4-Benzyl-1,3-diphenyl-1,2,4-benzotriazine；4-benzyl-1,3-diphenyl-1,2,4-benzotriazine
• CAS: 74172-90-0
• 化学式: C₂₆H₂₁N₃
• 分子量: 375.473
• InChiKey: QDAUGWSSWRUTGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  18.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲酸2-(2-硝基苯基)酰肼 在 tin 、 溶剂黄146 作用下， 以 四氢呋喃 、 二丁醚 为溶剂， 反应 1.75h， 生成 4-Benzyl-1,4-dihydro-1,3-diphenyl-1,2,4-benzotriazin
  参考文献：
  名称：

  Access to 1,4-Dihydrobenzo[e][1,2,4]triazin-4-yl Derivatives

  摘要：

  A simple, one-pot method for the preparation of 1 -aryl-3-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals by addition of aryllithium to the readily available 3-phenylbenzo[e][1,2,4]triazine followed by aerial oxidation is described. The intermediate anion is also trapped as an N-benzyloxycarbonyl derivative and purified prior to deprotection and oxidation to the radical. The method was demonstrated for nine (het)arenes, and the regioselectivity of nucleophilic addition to the benzo [e] [1,2,4]triazine and trapping of the intermediate anion with electrophiles was assessed computationally.

  DOI：

  10.1021/acs.orglett.5b03528

文献信息

• Neugebauer, Franz Alfred; Umminger, Irmgard, Chemische Berichte, 1980, vol. 113, # 4, p. 1205 - 1225
  作者：Neugebauer, Franz Alfred、Umminger, Irmgard

  DOI：——

  日期：——
• Chirality of the trisubstituted nitrogen center – XRD, dynamic NMR, and DFT investigation of 1,2-dihydrobenzo[e][1,2,4]triazine derivatives
  作者：Piotr Kaszyński、Arkadiusz Kłys、Sławomir Domagała、Krzysztof Woźniak

  DOI：10.1016/j.tet.2017.05.032

  日期：2017.7

  Molecular structures of two 1-aryl-2-benzyloxycarbonyl-1,2-dihydrobenzo[e][1,2,4]triazines 1 were established by single crystal XRD and compared to those of 4-benzyloxycarbonyl (2) and 4-benzyl (4) analogues. The structures revealed a highly pyramidalized asymmetric N(1) center stabilized by steric interactions in 1, but not in 2 and 3. Activation parameters for enantiomer interconversion were obtained by DNMR methods in C6D5Cl: Delta H-double dagger = 18.1(1) kcal mol(-1), Delta S-double dagger= -0.6(1) cal mol(-1) K-1 for Ar = Ph (1a) and Delta H-double dagger = 18.6(4) kcal mol(-1), Delta S-double dagger = 5.2(6) cal mol(-1) K-1 for Ar = 2-anisyl (1b). DFT computational investigation of the origin of the interconversion barrier on model compounds revealed steric destabilization of the inversion TS. (C) 2017 Elsevier Ltd. All rights reserved.
• Access to 1,4-Dihydrobenzo[<i>e</i>][1,2,4]triazin-4-yl Derivatives
  作者：Christos P. Constantinides、Emilia Obijalska、Piotr Kaszyński

  DOI：10.1021/acs.orglett.5b03528

  日期：2016.3.4

  A simple, one-pot method for the preparation of 1 -aryl-3-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals by addition of aryllithium to the readily available 3-phenylbenzo[e][1,2,4]triazine followed by aerial oxidation is described. The intermediate anion is also trapped as an N-benzyloxycarbonyl derivative and purified prior to deprotection and oxidation to the radical. The method was demonstrated for nine (het)arenes, and the regioselectivity of nucleophilic addition to the benzo [e] [1,2,4]triazine and trapping of the intermediate anion with electrophiles was assessed computationally.