6-phenyl-1,2,3,4-tetrahydropyridine

• 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-phenyl-1,2,3,4-tetrahydropyridine
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: DENLOAFFAKFBAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 bis-triphenylphosphine-palladium(II) chloride 六甲基磷酰三胺 、 三氟甲磺酸三甲基硅酯 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 6-phenyl-1,2,3,4-tetrahydropyridine
  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

• Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
  作者：Joshua J. Clarke、Yuuki Maekawa、Masakazu Nambo、Cathleen M. Crudden

  DOI：10.1021/acs.orglett.1c01892

  日期：2021.9.3

  Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation

  在氢硅烷和氢气氛的存在下，介离子卡宾稳定的硼离子有效地将取代的吡啶还原为哌啶。对照实验和氘标记研究证明了吡啶的可逆氢化硅烷化，能够在较温和的条件下完全还原 N-杂环。硅烷是防止哌啶产物和硼催化剂之间形成加合物的关键反应组分。
• [EN] ELECTRON TRANSPORT MATERIAL AND ORGANIC ELECTROLUMINESCENT ELEMENTS USING SAME<br/>[FR] MATIÈRE DE TRANSPORT D'ÉLECTRONS ET ÉLÉMENTS ÉLECTROLUMINESCENTS ORGANIQUES UTILISANT CELLE-CI
  申请人：JNC CORP

  公开号：WO2012005214A1

  公开（公告）日：2012-01-12

  本発明の式（１）で表される化合物は、有機ＥＬ素子の電子輸送材料として有用であり、この電子輸送材料を用いることによって有機ＥＬ素子の長寿命化等に寄与する。 式（１）中、Ｐｙは下記式（２）、（３）、（４）および（５）で表される１価の基の群から選ばれる１つであり；Ａｒ１はナフタレン－１，４－ジイルまたはナフタレン－１，５－ジイルであり；Ａｒ２はフェニルまたは２－ナフチルである。Ｐｙ、Ａｒ１およびＡｒ２の任意の水素は炭素数１～６のアルキルおよび／または炭素数３～６のシクロアルキルで置き換えられていてもよい。
• 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.