N-methoxycarbonyl-2-phenyl-1,2,3,4-tetrahydropyridine | 125592-91-8

• 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: N-methoxycarbonyl-2-phenyl-1,2,3,4-tetrahydropyridine
• 英文别名: methyl 2-phenyl-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 125592-91-8
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: CMWHOOQRJJWDIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,O-bis(methoxycarbonyl)-N-[(2-phenylcyclobutyl)methyl]hydroxylamine 500.0 ℃ 、1.33 Pa 条件下， 以13%的产率得到N-methoxycarbonyl-2-phenyl-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Thermal Reactions ofN-Acyl Phenylcyclobutylimines

  摘要：

  AbstractFlash vacuum thermolysis of the parent and phenyl substituted N‐acyl cyclobutylimines 3 was under investigation. At 500 °C and 0.01 torr, 3d with phenyl group on C‐1 and 3e with phenyl group on C‐2 of cyclobutane ring underwent ring expansion processes to produce N‐acyl 1,2,3,4‐tetrahydropyridines 8d and 8e. Meanwhile the parent N‐acyl cyclobutylimines 3a together with the phenyl group on C‐3 (3c) and imine carbon (3b) proceeded a hydrogen shift reaction to afford N‐acylaminomethylenecyclobutanes 8a‐c. In addition, cycloreversion competed with ring expansion or hydrogen shift in all cases.

  DOI：

  10.1002/jccs.199800030

文献信息

• Regioselective palladium-catalyzed tandem .alpha.-arylation/isomerization of cyclic enamides
  作者：Kristina Nilsson、Anders Hallberg

  DOI：10.1021/jo00295a041

  日期：1990.4
• Thermal Reactions of<i>N</i>-Acyl Phenylcyclobutylimines
  作者：Pei-Lin Wu、Chang-Fu Chen

  DOI：10.1002/jccs.199800030

  日期：1998.2

  AbstractFlash vacuum thermolysis of the parent and phenyl substituted N‐acyl cyclobutylimines 3 was under investigation. At 500 °C and 0.01 torr, 3d with phenyl group on C‐1 and 3e with phenyl group on C‐2 of cyclobutane ring underwent ring expansion processes to produce N‐acyl 1,2,3,4‐tetrahydropyridines 8d and 8e. Meanwhile the parent N‐acyl cyclobutylimines 3a together with the phenyl group on C‐3 (3c) and imine carbon (3b) proceeded a hydrogen shift reaction to afford N‐acylaminomethylenecyclobutanes 8a‐c. In addition, cycloreversion competed with ring expansion or hydrogen shift in all cases.