pyridine-2-carboxylic acid sec-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: pyridine-2-carboxylic acid sec-butyl ester
• 英文别名: Butan-2-yl pyridine-2-carboxylate；butan-2-yl pyridine-2-carboxylate
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: UPGQGMLLXSNAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-吡啶甲酸 、 仲丁醇 在 4-二甲氨基吡啶 、 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 pyridine-2-carboxylic acid sec-butyl ester
  参考文献：
  名称：

  将脂肪族仲醇衍生为吡啶甲酸酯——手性固定相 HPLC 分析的新选择

  摘要：

  Derivatization of secondary alcohols ((RRCHOH)-R-1-C-2) to benzoates has frequently employed to determine enantiomer ratios using HPLC with chiral stationary phase (CSP). However, a small difference in substituents (R-1, R-2) often results in insufficient separation. To find an alternative derivatization that detects such a small difference, picolinates (2-pyridyl-(CO2CHRR2)-R-1) possessing Me/Et, Me/vinyl, Me/acetylenic, Et/n-Pr, and n-Pr/allyl substituents were prepared and separation efficiency was compared with that of benzoates ((PhCO2CHRR2)-R-1). Eight commercially available CSPs containing carbamates or benzoates of cellulose and amylose were examined to find that retention factors (k'(1) and k'(2)) and resolution (R-s) of picolinates were greater than those of the corresponding benzoates and that good to excellent R-s values (>= 1.25) were recorded over a wide range of CSPs.

  DOI：

  10.3987/com-18-s(t)17

文献信息

• No Stirring Necessary:  Parallel Carbonylation of Aryl Halides with CO and Various Alcohols under Pressure
  作者：Hans-Ulrich Blaser、Martin Diggelmann、Hans Meier、Frédéric Naud、Elke Scheppach、Anita Schnyder、Martin Studer

  DOI：10.1021/jo034112v

  日期：2003.5.1

  The parallel carbonylation of aryl halides with 6-25 bar of CO in 1-mL vials in a standard autoclave was investigated. 4-Bromoacetophenone and 2-chloropyridine were used as model substrates with 102 different O-nucleophiles (primary and secondary alcohols, phenols). No inertization during the loading was necessary. Fifty esters (43 new, yield up to 60%) were isolated and characterized. Ether, ester, ketone, and sometimes even olefin functions were usually tolerated. The new method is suitable for screening and small scale products synthesis.
• Catalytic Synthesis and Asymmetric Reduction of Pyridylglyoxylic Amides and Esters
  作者：Samuel Couve-Bonnaire、Jean-François Carpentier、André Mortreux、Yves Castanet

  DOI：10.1002/1615-4169(20010330)343:3<289::aid-adsc289>3.0.co;2-1

  日期：2001.3.30

  The preparation of 2-pyridyl- and 4-pyridylglyoxylic esters and amides in moderate to high yields via palladium-catalyzed double carbonylation of 2-iodo- and 4-iodopyridines is reported. The effect of temperature, CO pressure, solvent, nature and concentration of nucleophile, nature of catalyst precursor, and substituents on iodopyridines has been investigated. The reduction of 4-pyridylglyoxylate esters into the corresponding alpha -hydroxy esters via ruthenium-catalyzed asymmetric hydrogenation or using alpine-borane proceeded in high yields but poor enantioselectivity. The results for the carbonylation and the hydrogenation catalytic processes are discussed in terms of electronic effects induced by the pyridyl ring.
• Derivatization of Secondary Aliphatic Alcohols to Picolinates – A New Option for HPLC Analysis with Chiral Stationary Phase
  作者：Yuichi Kobayashi、Keita Nishimura、Shuhei Tanabe、Riku Shinohara

  DOI：10.3987/com-18-s(t)17

  日期：——

  Derivatization of secondary alcohols ((RRCHOH)-R-1-C-2) to benzoates has frequently employed to determine enantiomer ratios using HPLC with chiral stationary phase (CSP). However, a small difference in substituents (R-1, R-2) often results in insufficient separation. To find an alternative derivatization that detects such a small difference, picolinates (2-pyridyl-(CO2CHRR2)-R-1) possessing Me/Et, Me/vinyl, Me/acetylenic, Et/n-Pr, and n-Pr/allyl substituents were prepared and separation efficiency was compared with that of benzoates ((PhCO2CHRR2)-R-1). Eight commercially available CSPs containing carbamates or benzoates of cellulose and amylose were examined to find that retention factors (k'(1) and k'(2)) and resolution (R-s) of picolinates were greater than those of the corresponding benzoates and that good to excellent R-s values (>= 1.25) were recorded over a wide range of CSPs.