1-pyridinio(p-methoxybenzenethiocarbonyl)amidate | 87290-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-pyridinio(p-methoxybenzenethiocarbonyl)amidate
• 英文别名: 4-methoxy-N-pyridin-1-ium-1-ylbenzenecarboximidothioate
• CAS: 87290-02-6
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: KXRFNLFLUWUBLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-pyridinio(p-methoxybenzenethiocarbonyl)amidate 、 碘甲烷 生成 1-{[1-(4-Methoxy-phenyl)-1-methylsulfanyl-meth-(Z)-ylidene]-amino}-pyridinium; iodide
  参考文献：
  名称：

  YOSHIDA, HIROSHI;URUSHIBATA, KIYOMI;OGATA, TSUYOSHI, BULL. CHEM. SOC. JAP., 1983, 56, N 5, 1561-1562

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯二硫代甲酸甲酯 、 1-氨基吡啶碘 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以93%的产率得到1-pyridinio(p-methoxybenzenethiocarbonyl)amidate
  参考文献：
  名称：

  Preparation of New Nitrogen-Bridged Heterocycles. 43.¹ Synthesis and Reaction of 5aH-Pyrido[1,2-d][1,3,4]thiadiazepine Derivatives

  摘要：

  Reactions of some 1-pyridinio- and 1-(4-methylpyridinio)(arenethiocarbonyl) with dimethyl acetylenedicarboxylate in chloroform afforded neither the expected dimethyl 2-aryl-5aH-pyrido-[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates nor their intramolecular Diels-Alder adducts, but gave novel rearranged products, dimethyl 4-aryl-5-thia-2,3-diazatricyclo[4.3.2.0(2,7)]undeca-3,8,10-triene-6,11-dicarboxylates in low to moderate yields. On the other hand, similar reactions of 1-(3-methylpyridinio)- and 1-(2-methylquinolinio)(arenethiocarbonyl)amidates with the same reagent provided 1:1 primary adducts, dimethyl 2-aryl-6-methyl-5aH-pyrido[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates and dimethyl 2-aryl-5a-methyl-5aH-[1,3,4]thiadiazepino[4,5-alpha]quinoline-4,5-dicarboxylates, respectively.

  DOI：

  10.1021/jo971066o

文献信息

• Pyridinium-1-thioacylaminides
  作者：Hiroshi Yoshida、Kiyomi Urushibata、Tsuyoshi Ogata

  DOI：10.1246/bcsj.56.1561

  日期：1983.5

  Pyridinium-, 2-methylpyridinium-, and 2,6-dimethylpyridinium-1-thioacylaminides (5–7) were prepared from the corresponding unsubstituted pyridinium-1-aminides and methyl dithiocarboxylates in fairly good yields. The alkylation reaction of 5–7 took place exclusively on the thiocarbonyl sulfur, yielding pyridinium salts in quantitative yields. The NMR spectroscopic studies indicated that E and Z forms existed for these pyridinium salts. The thermal decomposition of 5–7 yielded the corresponding pyridine, nitrile, and sulfur in good yields.

  以相应的未取代的吡啶-1-酰胺和二硫代羧酸甲酯为原料，制备了吡啶-1-酰胺、2-甲基吡啶-1-酰胺和 2,6-二甲基吡啶-1-硫代羧酸酰胺（5-7），收率相当高。5-7 的烷基化反应完全发生在硫代羰基硫上，定量生成吡啶鎓盐。核磁共振光谱研究表明，这些吡啶鎓盐存在 E 和 Z 两种形式。5-7 的热分解产生了相应的吡啶、腈和硫，收率很高。