3-methylthio-[1,2,4]triazolo[3,4-a]phthalazin-6(5H)-one | 502934-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-methylthio-[1,2,4]triazolo[3,4-a]phthalazin-6(5H)-one
• CAS: 502934-53-4
• 化学式: C₁₀H₈N₄OS
• 分子量: 232.266
• InChiKey: YRXNDYIZUZALBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.05
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-methylthio-[1,2,4]triazolo[3,4-a]phthalazin-6(5H)-one 在 四丁基氢氧化铵 、 silica gel 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.33h， 生成 5-methyl-3-methylthio-[1,2,4]triazolo[3,4-a]phthalazin-6(5H)-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
• 作为产物：
  描述：

  [1,2,4]triazolo[4,3-a]phthalazine-6(5H)-one-3(2H)-thione 、 碘甲烷 在 四丁基氢氧化铵 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.33h， 以85%的产率得到3-methylthio-[1,2,4]triazolo[3,4-a]phthalazin-6(5H)-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