3-Nitrophenyl picolinate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-Nitrophenyl picolinate
• 英文别名: (3-Nitrophenyl) pyridine-2-carboxylate
• 化学式: C₁₂H₈N₂O₄
• 分子量: 244.207
• InChiKey: UFEITKZJZGELAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Nitrophenyl picolinate 在 水 、 铜 作用下， 生成 2-吡啶甲酸 、 间硝基苯酚
  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 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-Nitrophenyl picolinate
  参考文献：
  名称：

  用氧离子化学合成铬（3，4-二氢苯并吡喃）的杂狄尔斯-阿尔德方法：Oxa-Povarov反应

  摘要：

  已经开发出了众所周知的Povarov反应的氧杂类似物，用于合成3，4-二氢苯并吡喃（chromans）。该反应涉及原位生成的阳离子芳基2-氧杂二烯氧碳鎓离子与烯烃的形式逆电子需量[4 + 2]环加成反应。氧离子中间体是通过路易斯酸（SnCl 4）促进酚衍生的Rychnovsky型混合乙缩醛的反应而生成的。发现苯并二氢吡喃产物的产率和非对映选择性取决于前体烯烃（即，单取代的，反式或顺式-二取代的和环状的烯烃）的取代方式。一般来说，反应得到内切非对映体为主要产品，除了的反应，反式-β-甲基，其承受外-色度。产物分布的从的反应的比较反式-和顺-β甲基表明该反应进行，至少部分地由一个nonconcerted离子通路。就像aza-Povarov反应一样，有两种潜在的反应机理。第一种机制涉及直接的异步[4 + 2]环加成途径，而第二种机制是通过将烯烃逐步Prins加成到芳基2-恶二烯氧鎓离子上，然后发

  DOI：

  10.1021/jo302328s

文献信息

• One pot synthesis of diarylfurans from aryl esters and PhI(OAc)₂via palladium-associated iodonium ylides
  作者：Yong-Sheng Bao、Bao Agula、Bao Zhaorigetu、Meilin Jia、Menghe Baiyin

  DOI：10.1039/c5ob00273g

  日期：——

  The example of palladium-catalyzed intermolecular cyclization for the synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and the other one from PhI(OAc)2 has been reported. The reaction is carried out through two steps: the rearrangement of palladium-associated iodonium ylides to form o-iodo diaryl ether and then palladium catalyzed

  已经报道了用于合成各种二芳基呋喃的钯催化的分子间环化的例子，其中芳环之一来自起始酯的酚部分，另一个芳环来自PhI（OAc）2。该反应通过两个步骤进行：与钯缔合的碘鎓基化物的重排以形成邻碘二芳基醚，然后由钯催化的分子内直接芳基化。该反应可以耐受多种官能团，并且是先前合成二芳基呋喃的方法的替代或补充。
• Leaving group effect in the cleavage of picolinate esters catalyzed by hydroxy-functionalized metallomicelles
  作者：Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo00080a006

  日期：1994.1

  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)
• A Hetero Diels–Alder Approach to the Synthesis of Chromans (3,4-Dihydrobenzopyrans) Using Oxonium Ion Chemistry: The Oxa-Povarov Reaction
  作者：Rivka R. R. Taylor、Robert A. Batey

  DOI：10.1021/jo302328s

  日期：2013.2.15

  for the synthesis of 3,4-dihydrobenzopyrans (chromans). The reaction involves the formal inverse electron demand [4 + 2] cycloaddition reaction of in situ-generated cationic aryl 2-oxadiene oxocarbenium ions with alkenes. The oxonium ion intermediates are generated through Lewis acid (SnCl4)-promoted reactions of phenol-derived Rychnovsky-type mixed acetals. The yield and diastereoselectivity of the

  已经开发出了众所周知的Povarov反应的氧杂类似物，用于合成3，4-二氢苯并吡喃（chromans）。该反应涉及原位生成的阳离子芳基2-氧杂二烯氧碳鎓离子与烯烃的形式逆电子需量[4 + 2]环加成反应。氧离子中间体是通过路易斯酸（SnCl 4）促进酚衍生的Rychnovsky型混合乙缩醛的反应而生成的。发现苯并二氢吡喃产物的产率和非对映选择性取决于前体烯烃（即，单取代的，反式或顺式-二取代的和环状的烯烃）的取代方式。一般来说，反应得到内切非对映体为主要产品，除了的反应，反式-β-甲基，其承受外-色度。产物分布的从的反应的比较反式-和顺-β甲基表明该反应进行，至少部分地由一个nonconcerted离子通路。就像aza-Povarov反应一样，有两种潜在的反应机理。第一种机制涉及直接的异步[4 + 2]环加成途径，而第二种机制是通过将烯烃逐步Prins加成到芳基2-恶二烯氧鎓离子上，然后发