1-amino-3-methylpyridin-1-ium iodide | 7583-91-7

• 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-amino-3-methylpyridin-1-ium iodide
• 英文别名: Pyridinium, 1-amino-3-methyl-, iodide；3-methylpyridin-1-ium-1-amine;iodide
• CAS: 7583-91-7
• 化学式: C₆H₉N₂*I
• 分子量: 236.055
• InChiKey: BPTBUSYOFJZQFD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-amino-3-methylpyridin-1-ium iodide 在 sodium ethanolate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 6-Methyl-10-p-tolyl-11-thia-8,9-diaza-tricyclo[5.4.0.0^4,8]undeca-2,5,9-triene-1,2-dicarboxylic acid dimethyl ester
  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
• 作为产物：
  描述：

  3-甲基吡啶 在 氢碘酸 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 为溶剂， 以30%的产率得到1-amino-3-methylpyridin-1-ium iodide
  参考文献：
  名称：

  Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region

  摘要：

  A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P-1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P-1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P-1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.126

文献信息

• Synthesis of Functionalized Pyrazolo[1,5-a]pyridines: [3+2] Cycloaddition of N-Aminopyridines and α,β-Unsaturated Carbonyl Compounds/Alkenes at Room Temperature
  作者：Chitrakar Ravi、Supravat Samanta、Darapaneni Mohan、N. Reddy、Subbarayappa Adimurthy

  DOI：10.1055/s-0036-1588753

  日期：2017.6

  through oxidative [3+2] cycloaddition of N-aminopyridines with α,β-unsaturated carbonyl compounds or electron-withdrawing olefins is described. The reactions proceed in N-methylpyrrolidone as the solvent under metal-free conditions at room temperature. The synthesis of functionalized pyrazolo[1,5-a]pyridines through oxidative [3+2] cycloaddition of N-aminopyridines with α,β-unsaturated carbonyl compounds

  摘要 描述了通过N-氨基吡啶与α，β-不饱和羰基化合物或吸电子烯烃的氧化[3 + 2]环加成反应，合成官能化的吡唑并[1,5- a ]吡啶。反应在室温下在无金属条件下在N-甲基吡咯烷酮作为溶剂中进行。 描述了通过N-氨基吡啶与α，β-不饱和羰基化合物或吸电子烯烃的氧化[3 + 2]环加成反应，合成官能化的吡唑并[1,5- a ]吡啶。反应在室温下在无金属条件下在N-甲基吡咯烷酮作为溶剂中进行。
• Design, synthesis and biological evaluation of new rhodacyanine analogues as potential antitumor agents
  作者：Yang Xiong Li、Xin Zhai、Wei Ke Liao、Wu Fu Zhu、Ying He、Ping Gong

  DOI：10.1016/j.cclet.2012.01.015

  日期：2012.4

  attempt to develop potent antitumor agents, new rhodacyanine analogues containing the pyridinium ring ( 5a – 5h ), the isoquinolinium ring ( 6a – 6c ) and the quinolinium ring ( 7a – 7e ) linked to the rhodanine ring via N–N covalent bond were designed, synthesized and evaluated for antitumor activity against human lung cancer cell line (H460) by MTT assay in vitro . Most of the tested compounds showed enhanced

  摘要为了开发有效的抗肿瘤药物，新的含有酪氨酸环（5a-5h），异喹啉鎓环（6a-6c）和喹啉鎓环（7a-7e）的若丹菁类似物通过N–N共价键与罗丹宁环连接通过MTT法体外设计，合成并评价了对人肺癌细胞系（H460）的抗肿瘤活性。与先导化合物MKT-077相比，大多数测试化合物显示出增强的抗肿瘤活性，IC 50值为0.006至9.2μmol/ L。其中，最有前途的化合物7d（IC 50 = 0.006μmol/ L）的活性是MKT-077（IC 50 = 1.3μmol/ L）的216.7倍。讨论了目标化合物的初步结构-活性关系。
• [3+2] Cycloaddition of N-Aminopyridines and Perfluoroalkynylphosphonates: Facile Synthesis of Perfluoroalkylated Pyrazolo[1,5-a]pyridines Containing a Phosphonate Moiety
  作者：Hui Zhang、Weiguo Cao、Qi Huang、Dong He、Jing Han、Jie Chen、Weimin He、Hongmei Deng、Min Shao

  DOI：10.1055/s-0037-1610443

  日期：2018.9

  3-Zwitterions generated from N-aminopyridines in the presence of base are trapped by perfluoroalkynylphosphonates to yield a variety of perfluoroalkylated pyrazolo[1,5-a]pyridine derivatives bearing a phosphonate group. The salient features of these [3+2] cycloadditions include operational simplicity, good tolerance of functional groups, and good to excellent yields at room temperature. 1,3-Zwitterions generated

  §对这项工作有同等贡献。 抽象的 由N-氨基吡啶在碱存在下产生的1，3-两性离子被全氟炔基膦酸酯捕获，得到各种带有膦酸酯基团的全氟烷基化吡唑并[1，5- a ]吡啶衍生物。这些[3 + 2]环加成反应的显着特征包括操作简便，对官能团的良好耐受性以及在室温下良好至优异的收率。 由N-氨基吡啶在碱存在下产生的1，3-两性离子被全氟炔基膦酸酯捕获，得到各种带有膦酸酯基团的全氟烷基化吡唑并[1，5- a ]吡啶衍生物。这些[3 + 2]环加成反应的显着特征包括操作简便，对官能团的良好耐受性以及在室温下良好至优异的收率。
• Composition for dyeing keratin fibers comprising at least one cationic 3-amino-pyrazolopyridine derivative, and methods of use thereof
  申请人：Fadli Aziz

  公开号：US20070136959A1

  公开（公告）日：2007-06-21

  The present disclosure relates to a composition for the dyeing of keratin fibers, such as the hair, comprising at least oneoxidation base chosen from cationic 3-amino pyrazolo-[1,5-a]-pyridine derivatives and addition salts thereof, and a method employing this composition. The present disclosure also relates to cationic 3-amino pyrazolo-[1,5-a]-pyridine derivatives and the addition salts thereof.

  本公开涉及一种用于染色角蛋白纤维（如头发）的组合物，包括至少一种氧化碱，所述氧化碱选自阳离子3-氨基吡唑-1,5-吡啶衍生物及其加成盐，并且使用该组合物的方法。本公开还涉及阳离子3-氨基吡唑-1,5-吡啶衍生物及其加成盐。
• Preparation of New Nitrogen-Bridged Heterocycles. 42. Synthesis and the Reaction of Pyridinium<i>N</i>-Ylides Using Bifunctional Ethyl Thiocyanatoacetates
  作者：Akikazu Kakehi、Suketaka Ito、Yasunobu Hashimoto

  DOI：10.1246/bcsj.69.1769

  日期：1996.6

  cycloadditions of some pyridinium (unsymmetrically substituted cyanomethylide)s with dimethyl acetylenedicarboxylate (DMAD) in various solvents afforded only dimethyl 3-cyanoindolizine-1,2-dicarboxylate, except a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium t-butoxide, gave new bicyclic mesoionic compounds

  各种吡啶鎓（单取代的甲基化物）在硫氰酸乙酯或 2-硫氰酸根合丙酸乙酯中顺利地攻击氰基，以低到中等的产率得到相应的吡啶鎓（取代的氰基甲基化物），而吡啶鎓（未取代的酰胺化物）与在相同的试剂中酯羰基以可观的产率得到吡啶鎓（硫氰酸根合乙酰基）-或（2-硫氰酸根合丙基）酰胺。除了几个例子外，一些吡啶鎓（不对称取代的氰基甲基化物）与乙炔二甲酸二甲酯 (DMAD) 在各种溶剂中的 1,3-偶极环加成仅得到 3-氰基吲哚腙-1,2-二甲酸二甲酯。另一方面，用强碱（如叔丁醇钾）处理吡啶鎓（硫氰基乙酰基）-或（2-硫氰基丙酸基）酰胺，得到了新的双环介离子化合物 N-[2-(1,3,4-噻二唑并[3,2-a]吡啶并)]乙酰胺衍生物，收率适中。N-[1-(2-thiocyanatopyridinio)]aceta的中间体...