7-[(E)-hex-1-enyl]-2,3,4,5-tetrahydroazepine-1-carboxylic acid benzyl ester

• 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: 7-[(E)-hex-1-enyl]-2,3,4,5-tetrahydroazepine-1-carboxylic acid benzyl ester
• 英文别名: benzyl 7-[(E)-hex-1-enyl]-2,3,4,5-tetrahydroazepine-1-carboxylate
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: ACMQWKYAJCHMPA-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  benzyl 2-oxoazepane-1-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 六甲基磷酰三胺 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.25h， 生成 7-[(E)-hex-1-enyl]-2,3,4,5-tetrahydroazepine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Suzuki Reaction of Vinyl Triflates from Six- and Seven-Membered N-Alkoxycarbonyl Lactams with Boronic Acids and Esters

  摘要：

  The Pd(0)-catalyzed reaction of vinyl triflates from N-alkoxycarbonyl lactams with different boron compounds has been studied. The coupling reaction of alkenylboronates and arylboronic acids with six- and seven-membered lactam-derived N-alkoxycarbonyl vinyl triflates was feasible under very mild conditions in THF-water employing (Ph3P)(2)PdCl2 as a catalyst and Na2CO3 as a base, which provided in high yields the corresponding 6- or 7-substituted N-alkoxycarbonyl-3,4-dihydro-2H-pyridines and N-alkoxycarbonyl-2,3,4,5-tetrahydroazepines. Allylboronates reacted slower but, with vinyl triflates from delta -valerolactam, still gave acceptable yields of the coupling product. Alkylboronic acids required different reaction conditions, in particular the presence of Ag2O together with a base in anhydrous toluene and (dppf)PdCl2 as a catalyst, affording the corresponding 6-alkyl-N-alkoxycarbonyl-3,4-dihydro-2H-pyridines in high yields.

  DOI：

  10.1021/jo001807c

文献信息

• Suzuki Reaction of Vinyl Triflates from Six- and Seven-Membered <i>N</i>-Alkoxycarbonyl Lactams with Boronic Acids and Esters
  作者：Ernesto G. Occhiato、Andrea Trabocchi、Antonio Guarna

  DOI：10.1021/jo001807c

  日期：2001.4.1

  The Pd(0)-catalyzed reaction of vinyl triflates from N-alkoxycarbonyl lactams with different boron compounds has been studied. The coupling reaction of alkenylboronates and arylboronic acids with six- and seven-membered lactam-derived N-alkoxycarbonyl vinyl triflates was feasible under very mild conditions in THF-water employing (Ph3P)(2)PdCl2 as a catalyst and Na2CO3 as a base, which provided in high yields the corresponding 6- or 7-substituted N-alkoxycarbonyl-3,4-dihydro-2H-pyridines and N-alkoxycarbonyl-2,3,4,5-tetrahydroazepines. Allylboronates reacted slower but, with vinyl triflates from delta -valerolactam, still gave acceptable yields of the coupling product. Alkylboronic acids required different reaction conditions, in particular the presence of Ag2O together with a base in anhydrous toluene and (dppf)PdCl2 as a catalyst, affording the corresponding 6-alkyl-N-alkoxycarbonyl-3,4-dihydro-2H-pyridines in high yields.