6-methyl-1-phenylazepan-2-one | 156542-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-methyl-1-phenylazepan-2-one
• CAS: 156542-38-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: ITPYXTRUVVYVPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  碘苯 在 potassium phosphate 、 copper(l) iodide 、 氢气 、 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 2-甲基-2-丁醇 、 甲苯 为溶剂， 90.0~110.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 6-methyl-1-phenylazepan-2-one 、 5-methyl-N-phenylhex-5-enamide
  参考文献：
  名称：

  Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes

  摘要：

  A palladium(0)-catalyzed rearrangement of piperidones and piperidines bearing a spirocyclopropane ring was developed. The ring expansion reaction led to a variety of functionalized caprolactam and azepane products in good to excellent yields. Experimental and computational mechanistic studies revealed an initial oxidative addition of the distal carbon carbon bond of a cyclopropane ring to the palladium(0) catalyst and the relief of ring strain as a driving force for product formation.

  DOI：

  10.1021/acs.joc.5b01846

文献信息

• Structural determination of ε-lactams by ¹ H and ¹³ C NMR
  作者：Rubén Montalvo-González、Armando Ariza-Castolo

  DOI：10.1002/mrc.2504

  日期：2009.12

  AbstractThe thermodynamic products (ε‐lactams) of the degradation of ten different spirocyclic oxaziridines were analyzed by 1H and 13C NMR spectroscopy. The preferred conformations were determined by examining the homonuclear spin–spin coupling constant and the chemical shift effects of the N‐substituent and the alkyl group of the aliphatic ring on 1H and 13C NMR spectra. Copyright © 2009 John Wiley & Sons, Ltd.