1-nitrodithieno<3,4-b:3',4'-d>pyridine | 132491-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 1-nitrodithieno<3,4-b:3',4'-d>pyridine
• 英文别名: 1-Nitrodithieno[3,4-b:3,4-d]pyridine；3-nitro-4,11-dithia-7-azatricyclo[7.3.0.02,6]dodeca-1(12),2,5,7,9-pentaene
• CAS: 132491-67-9
• 化学式: C₉H₄N₂O₂S₂
• 分子量: 236.275
• InChiKey: YYQGWOKSCBOKIW-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：

  tert-butyl N-(4-bromo-5-nitrothiophen-3-yl)carbamate 、 2-呋喃硼酸 以55%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Experimental and theoretical study of orientation in the nitration of dithieno[3,4-b:3',4'-d]pyridine
  作者：Kalman J. Szabo、Anna Britta Hoernfeldt、Salo Gronowitz

  DOI：10.1021/jo00004a046

  日期：1991.2

  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.
• 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：——