4,5,6,7-tetrahydropyrido[4,3-g][1,2,4]thiadiazocino[2,3,4-cd]-[1,2,4]triazolo[4,3-b]pyridazine-9(8H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,5,6,7-tetrahydropyrido[4,3-g][1,2,4]thiadiazocino[2,3,4-cd]-[1,2,4]triazolo[4,3-b]pyridazine-9(8H)-one
• 英文别名: 5-Thia-2,3,10,15,18-pentazatetracyclo[8.7.1.04,18.012,17]octadeca-1,3,12(17),13,15-pentaen-11-one；5-thia-2,3,10,15,18-pentazatetracyclo[8.7.1.04,18.012,17]octadeca-1,3,12(17),13,15-pentaen-11-one
• 化学式: C₁₂H₁₁N₅OS
• 分子量: 273.318
• InChiKey: AHFVKNCPBZKNTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  pyrido[3,4-d][1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thione 在 四丁基氢氧化铵 、 silica gel 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 4,5,6,7-tetrahydropyrido[4,3-g][1,2,4]thiadiazocino[2,3,4-cd]-[1,2,4]triazolo[4,3-b]pyridazine-9(8H)-one
  参考文献：
  名称：

  Preparative and theoretical study on chain length-dependence and substrate selectivity in the cycloalkylation of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones

  摘要：

  Cyclization of condensed [1,2,4]triazolo[4,3-b]pyridazine-3(2H)-6(5H)-ones with alpha,omega-dibromoalkanes afforded a series of novel ring systems including zwitterions and isomeric tetracyclic lactams. The product distribution is controlled by the chain-length of the reagent, the polarity of the solvent and the structure of ring A in the substrate. The observed substrate selectivity was interpreted on the basis of amide-I IR frequencies and by the results of ab initio B3LYP DFr calculations carried out at 6-31 G and 6-31 G(d) basis sets using IPCM solvation model. The cycloalkylation with 1,4-dibromobutane gave also macrocyles as detectable by-products which underwent ring contraction yielding lactams on attempted chromatographic separation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01156-0

文献信息

• Preparative and theoretical study on chain length-dependence and substrate selectivity in the cycloalkylation of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones
  作者：Antal Csámpai、Mónika Simó、Zoltán Szlávik、András Kotschy、Gábor Magyarfalvi、György Túrós

  DOI：10.1016/s0040-4020(02)01156-0

  日期：2002.10

  Cyclization of condensed [1,2,4]triazolo[4,3-b]pyridazine-3(2H)-6(5H)-ones with alpha,omega-dibromoalkanes afforded a series of novel ring systems including zwitterions and isomeric tetracyclic lactams. The product distribution is controlled by the chain-length of the reagent, the polarity of the solvent and the structure of ring A in the substrate. The observed substrate selectivity was interpreted on the basis of amide-I IR frequencies and by the results of ab initio B3LYP DFr calculations carried out at 6-31 G and 6-31 G(d) basis sets using IPCM solvation model. The cycloalkylation with 1,4-dibromobutane gave also macrocyles as detectable by-products which underwent ring contraction yielding lactams on attempted chromatographic separation. (C) 2002 Elsevier Science Ltd. All rights reserved.