5-amino-4-[(pyren-1-yl)methylidene]-2,1,3-benzothiadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5-amino-4-[(pyren-1-yl)methylidene]-2,1,3-benzothiadiazole
• 化学式: C₂₃H₁₄N₄S
• 分子量: 378.457
• InChiKey: AWTOPAATOUZOKK-BRJLIKDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-芘甲醛 、 2,1,3-苯并噻二唑-4,5-二胺 以 甲苯 为溶剂， 反应 6.0h， 以15%的产率得到7-Pyren-1-yl-8-pyren-1-ylmethyl-8H-imidazo[4',5':3,4]benzo[1,2-c][1,2,5]thiadiazole
  参考文献：
  名称：

  Site-selective formation of N-arylmethylimidazoles and C-arylimines in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with aromatic aldehydes

  摘要：

  Regioselective formation of N-arylmethylimidazoles and C-arylimines was found in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with selected aromatic aldehydes. The regiochemistry of the reaction products was confirmed by single crystal X-ray analysis. Gibbs free energy calculation using DFT method at the B3LYP/6-31G(d) level supports the regio-selectivity observed. The 4-imine obtained in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with pyrene-1-carboxaldehyde showed an unusually low magnetic field shift of the imine proton that was reproduced by molecular calculations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.006

文献信息

• Site-selective formation of N-arylmethylimidazoles and C-arylimines in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with aromatic aldehydes
  作者：Akihito Saitoh、Keiji Okinaka、Koichi Suzuki、Akihiro Seno、Maki Kasahara、Kazunori Ueno、Taisuke Matsumoto、Shuntaro Mataka

  DOI：10.1016/j.tet.2004.02.006

  日期：2004.3

  Regioselective formation of N-arylmethylimidazoles and C-arylimines was found in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with selected aromatic aldehydes. The regiochemistry of the reaction products was confirmed by single crystal X-ray analysis. Gibbs free energy calculation using DFT method at the B3LYP/6-31G(d) level supports the regio-selectivity observed. The 4-imine obtained in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with pyrene-1-carboxaldehyde showed an unusually low magnetic field shift of the imine proton that was reproduced by molecular calculations. (C) 2004 Elsevier Ltd. All rights reserved.