1-benzyl-3-phenylpyridin-1-ium;chloride | 162411-79-2

• 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-benzyl-3-phenylpyridin-1-ium;chloride
• CAS: 162411-79-2
• 化学式: C₁₈H₁₆N*Cl
• 分子量: 281.785
• InChiKey: BJXCSZPOQOCAKW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2E,4E)-5-(diethylamino)-2-phenylpenta-2,4-dienal 、 benzylamine hydrochloride 以 正丁醇 为溶剂， 以96%的产率得到1-benzyl-3-phenylpyridin-1-ium;chloride
  参考文献：
  名称：

  Reaction of Aldimine Anions with Vinamidinium Chloride:  Three-Component Access to 3-Alkylpyridines and 3-Alkylpyridinium Salts and Access to 2-Alkyl Glutaconaldehyde Derivatives

  摘要：

  [GRAPHICS]N-tert-Butylimino derivatives of aldehydes were deprotonated with LDA and reacted with vinamidinium chloride to give 2-alkylaminopentadienimine derivatives, which were isolated as their corresponding hydrochloride in 68-81% yield. Reaction of these derivatives with ammonium acetate or salts of primary amines, in n-butanol at 80 degrees C, afforded the corresponding 3-alkylpyridines or 3-alkylpyridinium salts in high yield. Alkaline hydrolysis of 2-alkylaminopentadieneimine derivatives allowed a practical accesss to potassium salts of 2-alkylglutaconaldehyde.

  DOI：

  10.1021/jo702311k

文献信息

• Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment
  作者：Ben W. Joynson、Graham R. Cumming、Liam T. Ball

  DOI：10.1002/anie.202305081

  日期：2023.8

  demonstrate that pyridinium and quinolinium salts can be accessed by the insertion of a single C-atom from an arylchlorodiazirine into the parent N-alkyl pyrrole or indole. The azinium products of ring expansion are activated towards oxygenation and hydrogenation, expediting further structural diversification. Safer methods for the use of diazirines as carbene precursors have been developed with insight

  我们证明，吡啶盐和喹啉盐可以通过将芳基氯二嗪中的单个 C 原子插入母体 N-烷基吡咯或吲哚来获得。扩环的氮化产物被激活，进行氧化和氢化，加速了进一步的结构多样化。利用差示扫描量热法的洞察力，已经开发了使用二嗪嗪作为卡宾前体的更安全的方法。
• Reaction of Aldimine Anions with Vinamidinium Chloride:  Three-Component Access to 3-Alkylpyridines and 3-Alkylpyridinium Salts and Access to 2-Alkyl Glutaconaldehyde Derivatives
  作者：Jean-Charles Wypych、Tuan Minh Nguyen、Michel Bénéchie、Christian Marazano

  DOI：10.1021/jo702311k

  日期：2008.2.1

  [GRAPHICS]N-tert-Butylimino derivatives of aldehydes were deprotonated with LDA and reacted with vinamidinium chloride to give 2-alkylaminopentadienimine derivatives, which were isolated as their corresponding hydrochloride in 68-81% yield. Reaction of these derivatives with ammonium acetate or salts of primary amines, in n-butanol at 80 degrees C, afforded the corresponding 3-alkylpyridines or 3-alkylpyridinium salts in high yield. Alkaline hydrolysis of 2-alkylaminopentadieneimine derivatives allowed a practical accesss to potassium salts of 2-alkylglutaconaldehyde.