pyridine-2-carboxylic acid 2-methoxyethyl ester | 153621-46-6

• 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 2-methoxyethyl ester
• 英文别名: 2-Methoxyethyl picolinate；2-Methoxyethyl pyridine-2-carboxylate
• CAS: 153621-46-6
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: XRYUDHIMWBGXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyridine-2-carboxylic acid 2-methoxyethyl ester 在 水 、 铜 作用下， 生成 2-吡啶甲酸 、 乙二醇甲醚
  参考文献：
  名称：

  Leaving group effect in the cleavage of picolinate esters catalyzed by hydroxy-functionalized metallomicelles

  摘要：

  Micellar aggregates of complexes of transition metal ions with the hydroxy-functionalized surfactant 1a are very effective catalysts of the cleavage of activated esters of alpha-amino acids. To ascertain their effectiveness toward unactivated esters, a systematic kinetic study was undertaken employing as substrates the picolinic acid esters 3a-1, the pK(a) of their alcoholic portion spanning more than 12 units from 3.6 to 16. The leaving group effect was investigated in water, pH=6.3, in the absence and presence of CU2+ ions, in the presence of the nonmicellar complex 2-CU2+, and in the presence of micellar aggregates made of 1a-Cu2+ or of its O-methylated analog 1b-Cu2+. In the presence of free metal ions the leaving group effect is negligible in the case of esters with good leaving groups (pK(a)

  DOI：

  10.1021/jo00080a006
• 作为产物：
  描述：

  2-吡啶甲酸 、 乙二醇甲醚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以54%的产率得到pyridine-2-carboxylic acid 2-methoxyethyl ester
  参考文献：
  名称：

  Leaving group effect in the cleavage of picolinate esters catalyzed by hydroxy-functionalized metallomicelles

  摘要：

  Micellar aggregates of complexes of transition metal ions with the hydroxy-functionalized surfactant 1a are very effective catalysts of the cleavage of activated esters of alpha-amino acids. To ascertain their effectiveness toward unactivated esters, a systematic kinetic study was undertaken employing as substrates the picolinic acid esters 3a-1, the pK(a) of their alcoholic portion spanning more than 12 units from 3.6 to 16. The leaving group effect was investigated in water, pH=6.3, in the absence and presence of CU2+ ions, in the presence of the nonmicellar complex 2-CU2+, and in the presence of micellar aggregates made of 1a-Cu2+ or of its O-methylated analog 1b-Cu2+. In the presence of free metal ions the leaving group effect is negligible in the case of esters with good leaving groups (pK(a)

  DOI：

  10.1021/jo00080a006

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.