3-acetyl-N-benzylpyridinium chloride | 5096-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-N-benzylpyridinium chloride
• 英文别名: 3-aceto-1-benzylpyridinium chloride；3-acetyl-1-benzyl-pyridinium; chloride；3-Acetyl-1-benzyl-pyridinium; Chlorid；1-Benzyl-3-acetyl-pyridinium-chlorid；3-Acetyl-1-benzylpyridinium chloride；1-(1-benzylpyridin-1-ium-3-yl)ethanone;chloride
• CAS: 5096-12-8
• 化学式: C₁₄H₁₄NO*Cl
• 分子量: 247.724
• InChiKey: UOWKGIUYMOGOMF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-acetyl-N-benzylpyridinium chloride 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以48%的产率得到1-(1-benzyl-1,4,5,6-tetrahydropyridin-3-yl)ethanone
  参考文献：
  名称：

  Paglietti, Giuseppe; Sanna, Paolo; Nuvole, Antonio, Journal of Chemical Research, Miniprint, 1983, # 10, p. 2326 - 2342

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰基吡啶 、 氯化苄 在 甲醇 作用下， 生成 3-acetyl-N-benzylpyridinium chloride
  参考文献：
  名称：

  A Study of the Primary Acid Reaction on Model Compounds of Reduced Diphosphopyridine Nucleotide^1,2

  摘要：

  DOI：

  10.1021/ja01537a063

文献信息

• Covalent adducts from 1,3-disubstituted pyridinium salts and piperidine
  作者：F. Micheletti Moracci、B. Di Rienzo、S. Tortorella、F. Liberators

  DOI：10.1016/s0040-4020(01)93695-6

  日期：1980.1

  isolated from the reaction between piperidine and pyridinium salts 1a-f. 3a-f are stable both in the solid state and in apolar solvents, whereas their fast dissociation back to piperidine and pyridinium ions occurs in aqueous solution. The latter, in the alkaline environment produced by the amine, yields the correspondent pseudobases, which are key intermediates of the subsequent reactions. For instance

  从哌啶和吡啶鎓盐1a-f之间的反应中分离出共价加合物3a -f。3a-f在固态和非极性溶剂中都是稳定的，而它们在水溶液中快速解离回到哌啶和吡啶鎓离子。在胺产生的碱性环境中，后者产生相应的假碱，它们是后续反应的关键中间体。例如，来自1a，b的假碱基可以与相应的吡啶鎓阳离子进行开环反应或氧化还原过程。
• Generation and reactions of 1-(2-indolyl)vinylcopper derivatives with pyridinium salts
  作者：M.-Lluı̈sa Bennasar、Cecı́lia Juan、Tomàs Roca、Manuel Monerris、Joan Bosch

  DOI：10.1016/s0040-4020(01)01065-1

  日期：2001.12

  1-(2-Indolyl)vinylstannane 1b has been transmetallated into both the corresponding HO mixed cyanocuprate and the Cu-catalysed organomagnesium reagent, and the reactivity of these species towards N-alkyl-3-acylpyridinium salts 8 and 17 has been tested.

  1-（2-吲哚基）乙烯基锡烷1b已被金属转移到相应的HO混合氰铜酸盐和Cu催化的有机镁试剂中，并且已经测试了这些物质对N-烷基-3-酰基吡啶鎓盐8和17的反应性。
• Synthesis of 3,5-diacyl-4-phenyl-1,4-dihydropyridines
  作者：M.-Lluïsa Bennasar、Cecília Juan、Joan Bosch

  DOI：10.1016/s0040-4039(98)02084-x

  日期：1998.12

  via a regio- and chemoselective addition of Ph2Cu(CN)Li2 to β-substituted N-alkylpyridinium salts, followed by acylation of the intermediate 1,4-dihydropyridines with trichloroacetic anhydride and subsequent haloform-type reaction. A similar sequence using an N-silylpyridinium salt and PhMgBr allows the preparation of the corresponding N-unsubstituted dihydropyridines.

  3,5-二酰基-4-苯基-1,4-二氢吡啶是通过将Ph 2 Cu（CN）Li 2的区域和化学选择性加成到β-取代的N-烷基吡啶鎓盐中，然后将中间体1酰化而合成的，4-二氢吡啶与三氯乙酸酐和随后的卤仿型反应。使用N-甲硅烷基吡啶鎓盐和PhMgBr的相似序列使得可以制备相应的N-未取代的二氢吡啶。
• Addition of organocopper reagents to N-alkylpyridinium salts. A flexible access to polysubstituted dihydropyridines
  作者：M.-Lluı̈sa Bennasar、Cecı́lia Juan、Joan Bosch

  DOI：10.1016/s0040-4039(00)02006-2

  日期：2001.1

  The addition of a series of organocopper (alkyl, vinyl, allyl, and ethynyl) reagents to 3-acyl-N-alkylpyridinium salts, followed by acylation of the intermediate 1,4- or 1,2-dihydropyridines with trichloroacetic anhydride has been studied.

  研究了向3-酰基-N-烷基吡啶鎓盐中添加一系列有机铜（烷基，乙烯基，烯丙基和乙炔基）试剂，然后用三氯乙酸酐酰化中间体1,4-或1,2-二氢吡啶的方法。 。
• A short procedure for the preparation of highly functionalized di- and tetrahydropyridines
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Cecília Juan、Laura Llauger、Joan Bosch

  DOI：10.1016/s0040-4039(99)00621-8

  日期：1999.5

  The addition of a series of stabilized carbon nucleophiles to 3-acyl-1-alkylpyridinium salts. followed by acylation of the intermediate dihydropyridines with trichloroacetic anhydride has been studied. The C-4 adducts resulting from the addition of α-(methylsulfanyl)ester enolates have been converted into synthetically useful 1,2,3,4-tetrahydropyridines.

  向3-酰基-1-烷基吡啶鎓盐中添加一系列稳定的碳亲核试剂。然后研究了中间产物二氢吡啶与三氯乙酸酐的酰化作用。由α-（甲基硫烷基）酯烯酸酯的添加所产生的C-4加合物已被转化为合成上有用的1,2,3,4-四氢吡啶。