1-methyl-2-aminopyridinium iodide | 73813-27-1

• 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: 1-methyl-2-aminopyridinium iodide
• 英文别名: N-(1-methylpyridin-1-ium-2-yl)-1,1-bis(methylsulfanyl)methanimine;iodide
• CAS: 73813-27-1
• 化学式: C₉H₁₃N₂S₂*I
• 分子量: 340.252
• InChiKey: JGIDANQVIHYMRL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  16.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-2-aminopyridinium iodide 在 cesium fluoride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 168.0h， 生成 2-(1-methyl-1,2-dihydropyridylidene)amino-5-(4-chlorophenyl)oxazoline
  参考文献：
  名称：

  Fluoride Ion Promoted Azomethine Ylid Generation from 1-Methyl-2-[methylthio(trimethylsilylmethylimino)methylimino]-1,2-dihydropyridine, a Synthetic Equivalent of Aminonitrile Ylid

  摘要：

  1-Methyl-2-[methylthio(trimethylsilylmethylimino)methyl-imino]-1,2-dihydropyridine (1), prepared from 2-amino-1-methyl-pyridinium iodide in 3 steps, reacted with carbonyl compounds in the presence of cesium fluoride in acetonitrile to give 2-(1-methyl-1,2-dihydropyridylidene)aminooxazoline derivatives (6) via the 1,3-dipolar cycloadditon. This reaction was the first example of reaction of aminonitrile ylid with the C=O double bond.

  DOI：

  10.3987/com-94-6705
• 作为产物：
  描述：

  1-甲基-2(1H)-吡啶亚胺氢碘酸盐(1:1) 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-methyl-2-aminopyridinium iodide
  参考文献：
  名称：

  Fluoride Ion Promoted Azomethine Ylid Generation from 1-Methyl-2-[methylthio(trimethylsilylmethylimino)methylimino]-1,2-dihydropyridine, a Synthetic Equivalent of Aminonitrile Ylid

  摘要：

  1-Methyl-2-[methylthio(trimethylsilylmethylimino)methyl-imino]-1,2-dihydropyridine (1), prepared from 2-amino-1-methyl-pyridinium iodide in 3 steps, reacted with carbonyl compounds in the presence of cesium fluoride in acetonitrile to give 2-(1-methyl-1,2-dihydropyridylidene)aminooxazoline derivatives (6) via the 1,3-dipolar cycloadditon. This reaction was the first example of reaction of aminonitrile ylid with the C=O double bond.

  DOI：

  10.3987/com-94-6705

文献信息

• Synthesis and reactions of heterocyclic dithiocarbamates.
  作者：KAZUMICHI MIZUYAMA、YOSHINORI TOMINAGA、YOSHIRO MATSUDA、GORO KOBAYASHI

  DOI：10.1248/cpb.27.2879

  日期：——

  (Alkylthio) thiocarbonylimino-1-methyl-1, 2-dihydropyridine derivatives (3a-e) were prepared by the reaction of 2-amino-1-methylpyridinium iodide (1a-c or d) with carbon disulfide in the presence of sodium hydride and subsequent methylation with dimethyl sulfate in good yields. Similarly, 1-methyl-4-(methylthio) thiocarbonyl-1, 4-dihydropyridine (3i), 1-methyl-2-(methylthio) thiocarbonyl-1, 2-dihydrothiazole (3g), and 1-methyl-2-(methylthio) thiocarbonyl-1, 2-dihydrobenzothiazole (3h) were synthesized by the reaction of the corresponding 2-imino- and 4-imino-N-methyl heterocyclic compounds with carbon disulfide. The reaction of 3a-e with dimethyl acetylenedicarboxylate afforded the 2- or 4-[1, 2-bis (methoxycarbonyl)-2-thioxoethylidene]-1, 2- or 1, 4-dihydropyridine derivatives (8a-d). The reaction of 3i with dimethyl acetylenedicarboxylate (2 mol) gave cyclobuta [b] azocine (9). The reaction of 3h with dimethyl acetylenedicarboxylate afforded 2, 3-dihydrobenzothiazole-2-spiro-2'-(2H-pyrrole) (10). 2-[N-bis (methylthio) methylene] amino-N-methylpyridinium and benzothiazolium iodide (11b, c), which were prepared by the methylation of 3a and h with methyl iodide, reacted with nucleophiles to yield the corresponding products substituted on one or two methylthio groups.

  (在氢化钠存在下，2-氨基-1-甲基吡啶碘化物（1a-c 或 d）与二硫化碳反应，然后用硫酸二甲酯进行甲基化，制备了（烷硫基）硫代羰基亚氨基-1-甲基-1, 2-二氢吡啶衍生物（3a-e），产率良好。同样，通过相应的 2-亚氨基和 4-亚氨基-N-甲基杂环化合物与二硫化碳的反应，合成了 1-甲基-4-（甲硫基）硫代羰基-1，4-二氢吡啶（3i）、1-甲基-2-（甲硫基）硫代羰基-1，2-二氢噻唑（3g）和 1-甲基-2-（甲硫基）硫代羰基-1，2-二氢苯并噻唑（3h）。3a-e 与乙炔二甲酸二甲酯反应，可得到 2-或 4-[1，2-双（甲氧羰基）-2-硫酮亚乙基]-1，2-或 1，4-二氢吡啶衍生物（8a-d）。3i 与乙炔二甲酸二甲酯（2 摩尔）反应生成环丁[b]氮杂吖啶（9）。3h 与乙酰二羧酸二甲酯反应得到 2，3-二氢苯并噻唑-2-螺-2'-（2H-吡咯）（10）。由 3a 和 h 与碘甲烷甲基化制备的 2-[N-双（甲硫基）亚甲基]氨基-N-甲基吡啶鎓和苯并噻唑鎓碘化物（11b、c）与亲核剂发生反应，得到被一个或两个甲硫基取代的相应产物。
• Formal (3+2) Cycloaddition Reactions of 1-Methyl-2-(methylthio-(trimethylsilylmethylimino)methylimino)-1,2-dihydropyridine and Related Compound with Carbonyl Compounds Promoted by Fluoride Ion.
  作者：Shinya KOHRA、Kazuo UEDA、Yoshinori TOMINAGA

  DOI：10.1248/cpb.43.204

  日期：——

  Reaction of 1-methyl-2-[methylthio(trimethylsilylmethylimino)methylimino]-1, 2-dihydropyridine (1), prepared from 2-amino-1-methyl-pyridinium iodide in 3 steps, with carbonyl compounds in the presence of 2 eq of cesium fluoride in acetonitrile afforded 2-(1-methyl-1, 2-dihydropyridylidene)aminooxazoline derivatives (12), which correspond to formal [3+2] cycloadducts of the aminonitrile ylid. Further, compound 1 reacted with carbonyl compounds in the presence of a catalytic amount of tetra-n-butylammonium fluoride (TBAF) to give corresponding cycloadducts.

  由2-氨基-1-甲基-碘化吡啶鎓分3步制备得到的1-甲基-2-[甲硫基(三甲基甲硅烷基甲基亚氨基)甲基亚氨基]-1, 2-二氢吡啶(1)与羰基化合物在2当量存在下反应氟化铯在乙腈中的反应得到2-(1-甲基-1,2-二氢吡啶基)氨基恶唑啉衍生物(12)，其对应于氨基腈内鎓的形式[3+2]环加合物。此外，化合物1在催化量的四正丁基氟化铵(TBAF)存在下与羰基化合物反应，得到相应的环加合物。
• MIZUYAMA K.; TOMINAGA Y.; MATSUDA Y.; KOBAYASHI G., CHEM. AND PHARM. BULL., 1979, 27, NO 12, 2879-2889
  作者：MIZUYAMA K.、 TOMINAGA Y.、 MATSUDA Y.、 KOBAYASHI G.

  DOI：——

  日期：——
• Kohra Shinya, Tominaga Yoshinori, Heterocycles, 38 (1994) N 6, S 1217-1220
  作者：Kohra Shinya, Tominaga Yoshinori

  DOI：——

  日期：——