6-butyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

• 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: 6-butyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 6-butyl-3,4-dihydropyridine-1(2H)-carboxylate；tert-butyl 6-butyl-3,4-dihydro-2H-pyridine-1-carboxylate
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: ZTBWRBBPXVTZEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-butyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 在 四氢吡咯 、 di-tert-butoxydiazene 、 六正丁基二锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 tert-butyl 6-oxo-8-((phenylsulfonyl)methyl)octahydroquinoline-1(2H)-carboxylate
  参考文献：
  名称：

  Free-Radical Carbo-alkenylation of Enamides and Ene-carbamates

  摘要：

  The addition of xanthates and vinyldisulfones across the double bond of enamides and ene-carbamates provides access to the corresponding three.. component adducts in good to excellent yields with a high level of diastereocontrol in cyclic systems. This strategy illustrates a complementary reactivity for these versatile olefins and extends their scope of application.

  DOI：

  10.1021/ol401147w
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 六甲基磷酰三胺 、 potassium carbonate 、 silver(l) oxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 6-butyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl 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

• Free-Radical Carbo-alkenylation of Enamides and Ene-carbamates
  作者：Clément Poittevin、Virginie Liautard、Redouane Beniazza、Frédéric Robert、Yannick Landais

  DOI：10.1021/ol401147w

  日期：2013.6.7

  The addition of xanthates and vinyldisulfones across the double bond of enamides and ene-carbamates provides access to the corresponding three.. component adducts in good to excellent yields with a high level of diastereocontrol in cyclic systems. This strategy illustrates a complementary reactivity for these versatile olefins and extends their scope of application.
• 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.