5,6-dihydro-4H-[2,3']bipyridinyl-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: 5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 6-pyridin-3-yl-3,4-dihydro-2H-pyridine-1-carboxylate
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: FWXFGGVCRKBYCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester 在 palladium 10% on activated carbon 、 ammonium formate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到N-叔-丁氧羰基新烟碱
  参考文献：
  名称：

  Expedient Synthesis of α-Heteroaryl Piperidines Using a Pd-Catalyzed Suzuki Cross-Coupling–Reduction Sequence

  摘要：

  A method for the modular synthesis of alpha-heteroaryl piperidines is reported. The two-step procedure consists of an initial Pd-catalyzed Suzuki cross-coupling of the heteroaryl bromide with a boronate ester derived from N-Boc piperidone, followed by subsequent tetrahydropyridine reduction. Using this method, alpha-heteroaryl piperidine products featuring a broad range of pharmaceutically relevant azine and diazine substitutions have been prepared.

  DOI：

  10.1021/ol403367b
• 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 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pd(0)-Catalyzed Cross-Coupling Reactions of Boron Derivatives with a Lactam-Derived N-Boc Enol Triflate

  摘要：

  The cross-coupling reaction of 2-(1-alkenyl)-1,3,2-benzodioxaboroles, obtained from alkynes and catecholborane, and other boron derivatives with a lactam-derived N-Boc enol triflate occurred under very mild conditions in a THF-water medium employing (Ph3P)(2)PdCl2 as a catalyst, providing the corresponding B-substituted N-Boc 3,4-dihydro-2H-pyridines in high yields.

  DOI：

  10.1021/ol005759u

文献信息

• Trapping of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles: Controlling the formation of α-amino quaternary and vicinal stereocenters
  作者：Timothy K. Beng、Nathan Fox、Daniel P. Bassler、Amir Alwali、Kayla Sincavage、Ann Wens V. Silaire

  DOI：10.1039/c5ob01371b

  日期：——

  The interception of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles has led to the diastereoselective synthesis of vicinally functionalized piperidines bearing α-amino quaternary stereocenters.

  通过对碳锂化衍生的三级苄基α锂吡啶与碳亲电试剂的拦截，实现了含α-氨基季碳立体中心的邻位官能化吡啶的对映选择性合成。
• Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C–H activation/cross-coupling of cyclic enamides with boronic acids
  作者：Timothy K. Beng、Spencer Langevin、Hannah Braunstein、Monique Khim

  DOI：10.1039/c5ob02263k

  日期：——

  The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described. The desired outcome is achieved through ruthenium-catalyzed, site-selective sp2 C–H activation/cross-coupling with aryl and alkenyl boronic acids. The regioselectivity (α-sp2vs. α-sp3vs. β-sp2 C–H functionalization) is governed by the rate differences between

  描述了通过环酰胺的中间体合成α-芳基和烯基吡咯烷-，哌啶-和氮杂环庚烷衍生物。理想的结果是通过钌催化的，位点选择性的sp 2 C H活化/与芳基和烯基硼酸交叉偶联而实现的。区域选择性（α-SP 2 VS。α-SP 3 VS。β-SP 2 C-H官能化）是通过SP之间的速率差支配2和SP 3的钌金属和之间C-H活化和必要性螯合羰基导向基团。
• Pd(0)-Catalyzed Cross-Coupling Reactions of Boron Derivatives with a Lactam-Derived <i>N</i>-Boc Enol Triflate
  作者：Ernesto G. Occhiato、Andrea Trabocchi、Antonio Guarna

  DOI：10.1021/ol005759u

  日期：2000.5.1

  The cross-coupling reaction of 2-(1-alkenyl)-1,3,2-benzodioxaboroles, obtained from alkynes and catecholborane, and other boron derivatives with a lactam-derived N-Boc enol triflate occurred under very mild conditions in a THF-water medium employing (Ph3P)(2)PdCl2 as a catalyst, providing the corresponding B-substituted N-Boc 3,4-dihydro-2H-pyridines in high yields.
• Expedient Synthesis of α-Heteroaryl Piperidines Using a Pd-Catalyzed Suzuki Cross-Coupling–Reduction Sequence
  作者：Kevin D. Hesp、Dilinie P. Fernando、Wenhua Jiao、Allyn T. Londregan

  DOI：10.1021/ol403367b

  日期：2014.1.17

  A method for the modular synthesis of alpha-heteroaryl piperidines is reported. The two-step procedure consists of an initial Pd-catalyzed Suzuki cross-coupling of the heteroaryl bromide with a boronate ester derived from N-Boc piperidone, followed by subsequent tetrahydropyridine reduction. Using this method, alpha-heteroaryl piperidine products featuring a broad range of pharmaceutically relevant azine and diazine substitutions have been prepared.