3-nitrodithieno<3,4-b:3',4'-d>pyridine | 132491-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3-nitrodithieno<3,4-b:3',4'-d>pyridine
• 英文别名: 5-Nitro-4,11-dithia-7-azatricyclo[7.3.0.02,6]dodeca-1(12),2,5,7,9-pentaene
• CAS: 132491-69-1
• 化学式: C₉H₄N₂O₂S₂
• 分子量: 236.275
• InChiKey: PXWXUDKOHXBFND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dithieno<3,4-b:3',4'-d>pyridine 在 硝酸 作用下， 以 三氟乙酸 为溶剂， 反应 7.0h， 以28.6%的产率得到1-nitrodithieno<3,4-b:3',4'-d>pyridine
  参考文献：
  名称：

  Experimental and theoretical study of orientation in the nitration of dithieno[3,4-b:3',4'-d]pyridine

  摘要：

  The nitration of ditheino[3,4-b:3',4'-d]pyridine was investigated. Despite the similarity of the electrophilic reaction centers, high positional selectivity was found. Thus, the 1-, 8-, and 3-nitro isomers were obtained in the relative amounts 78%, 20%, and 2%, respectively. In spite of the unusually large size of the molecular systems, the structure and electronic properties of the Wheland intermediates (sigma complexes) and the transition states were calculated at the ab initio 3-21G* level. Harmonic frequencies have been calculated to characterize the stationary points obtained. The Wheland intermediate model failed to predict the site preferences, probably due to steric hindrance. However, the energies found for the transition-state complexes are in good agreement with the experimental findings. The transition-state geometry of the ring system shows greater similarity to the parent structure than to the Wheland intermediate. Orientation effects could be explained by the electron distribution of the transition-state structures.

  DOI：

  10.1021/jo00004a046

文献信息

• SZABO, KALMAN J.;HORNFELDT, ANNA-BRITTA;GRONOWITZ, SALO, J. ORG. CHEM., 56,(1991) N, C. 1590-1596
  作者：SZABO, KALMAN J.、HORNFELDT, ANNA-BRITTA、GRONOWITZ, SALO

  DOI：——

  日期：——