1-Benzyl-2,3,4,5-tetrahydropyridin-1-ium | 66120-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Benzyl-2,3,4,5-tetrahydropyridin-1-ium
• CAS: 66120-29-4
• 化学式: C₁₂H₁₆N
• 分子量: 174.266
• InChiKey: BOZAODHSNSDLSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2,3,4,5-tetrahydropyridin-1-ium 在 水 作用下， 以 甲苯 为溶剂， 生成 1-benzyl-N-cyclohexylpiperidine-2-carboxamide
  参考文献：
  名称：

  Regioselective Metal-Free Decarboxylative Multicomponent Coupling of α-Amino Acids, Aldehydes and Isonitriles Leading toN-Substituted Azacyclic-2-carboxamides with Antithrombotic Activity

  摘要：

  An atom-economical regioselective synthesis of N-substituted prolinamides or N-substituted piperidine-2-carboxamides via a metal-free decarboxylative multicomponent coupling between l-proline or pipecolic acid, aldehydes, and isonitriles is described. The cascade event involves sequential imine formation, decarboxylation, isonitrile insertion, and hydrolysis to afford the product in one-pot. Two of the prolinamides were found to display appreciable antithrombotic activity via inhibition of platelet aggregation.

  DOI：

  10.1021/jo502029k
• 作为产物：
  描述：

  以 甲苯 为溶剂， 生成 1-Benzyl-2,3,4,5-tetrahydropyridin-1-ium
  参考文献：
  名称：

  Regioselective Metal-Free Decarboxylative Multicomponent Coupling of α-Amino Acids, Aldehydes and Isonitriles Leading toN-Substituted Azacyclic-2-carboxamides with Antithrombotic Activity

  摘要：

  An atom-economical regioselective synthesis of N-substituted prolinamides or N-substituted piperidine-2-carboxamides via a metal-free decarboxylative multicomponent coupling between l-proline or pipecolic acid, aldehydes, and isonitriles is described. The cascade event involves sequential imine formation, decarboxylation, isonitrile insertion, and hydrolysis to afford the product in one-pot. Two of the prolinamides were found to display appreciable antithrombotic activity via inhibition of platelet aggregation.

  DOI：

  10.1021/jo502029k

文献信息

• Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C–H nucleophiles with low catalyst loading
  作者：Jing Guo、Ying Xie、Qiao-Lei Wu、Wen-Tian Zeng、Albert S. C. Chan、Jiang Weng、Gui Lu

  DOI：10.1039/c8ra02340a

  日期：——

  An aerobic decarboxylative cross-coupling of α-amino acids with diverse C–H nucleophiles has been realized using Cu2(OH)2CO3 (1 mol%) as the catalyst under air. This protocol enables highly efficient formation of various C(sp3)–C(sp3), C(sp3)–C(sp2) and C(sp3)–C(sp) bonds under simple conditions without the use of any ligand or extra oxidant, providing a practical approach to numerous nitrogen-containing

  使用Cu 2 (OH) 2 CO 3 (1 mol%)作为催化剂在空气下实现了α-氨基酸与多种C-H亲核试剂的需氧脱羧交叉偶联。该协议能够在简单的条件下高效形成各种 C(sp 3 )–C(sp 3 )、C(sp 3 )–C(sp 2 ) 和 C(sp 3 )–C(sp) 键，而无需使用任何配体或额外的氧化剂，为许多含氮化合物提供了一种实用的方法，产率从良好到极好。克级实验和 Rad51 抑制剂的三步合成也证明了效率和实用性。