2-methoxy-N-(pyridin-2-ylmethyl)benzamide | 57786-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-N-(pyridin-2-ylmethyl)benzamide
• CAS: 57786-40-0
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: DTHQZOFZHUGLTI-UHFFFAOYSA-N

物化性质

• 溶解度：
  >36.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-N-(pyridin-2-ylmethyl)benzamide 在 三溴化硼 、 三氯氧磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 3-(2'-hydroxyphenyl)imidazo<1,5-a>pyridine
  参考文献：
  名称：

  Photoinduced Intramolecular Proton Transfer and Charge Redistribution in Imidazopyridines

  摘要：

  The ground-state conformation and fluorescence properties of two closely related dyes 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine (1,2-HPIP) and 3-(2'-hydroxyphenyl)imidazo[1,5-a]pyridi (1,5-HPIP) have been studied in various solvents at room temperature to determine the origin of the large red-shifted emission spectra. The two compounds have a ground-state planar conformation stabilized by an intramolecular ii bond (MB) between the imino and phenol groups. On electronic excitation in cyclohexane solution a weak fluorescence is observed in the two dyes, with large Stokes shifts (1,2-HPIP: lambda(max) = 588 nm, Delta v = 11 000 cm(-1) 1,5-HPIP: lambda(max) 440 nm, Delta v = 9000 cm(-1)). For the first dye it is proposed that the emission takes place from a zwitterion produced by a proton-transfer reaction in the singlet manifold. A quinonoid, neutral phototautomer is excluded on the basis of the electronic structure of the molecule. In the case of 1,5-HPIP, the IHB is broken on electronic excitation and neither a proton nor H atom transfer occurs due to the reversal of the proton affinity of the imino group. The anomalous fluorescence is assigned to significant changes in the geometry of the emitting state following excitation.

  DOI：

  10.1021/j100001a014
• 作为产物：
  描述：

  2-氨甲基吡啶 、 邻甲氧基苯甲酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-methoxy-N-(pyridin-2-ylmethyl)benzamide
  参考文献：
  名称：

  烯丙基砜与甲基吡啶的无金属CC偶联，可通过吡啶引发的亚磺酸根阴离子原位生成乙烯基砜。

  摘要：

  乙烯基砜因其生物学活性和合成用途而享有特权。合成转化以有效地获得具有这些基序的高价值化合物是人们所期望和追求的。在本文中，描述了一种新的方法，可通过药理学上普遍的甲基吡啶酰胺的吡啶环附近的C（sp 3）-H键与烯基砜1-甲基-4-（丙基）的选择性官能化来形成含乙烯基砜的化合物-1,2-二烯-1-基磺酰基）苯。反应条件温和，不需要金属催化剂或添加剂，并且显示出良好的官能团耐受性。对于这种异常转化的机理研究表明，该反应通过罕见的吡啶引发的p-甲苯磺酸根阴离子介导的烯丙基砜的活化，类似于膦触发的反应。

  DOI：

  10.1021/acs.joc.0c00788

文献信息

• Metal-Free C–C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated In Situ Generation of Sulfinate Anion
  作者：Humair M. Omer、Peng Liu、Kay M. Brummond

  DOI：10.1021/acs.joc.0c00788

  日期：2020.6.19

  Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to form vinyl sulfone-containing compounds by selective functionalization of the C(sp3)–H bond adjacent to the pyridine ring of pharmacologically prevalent

  乙烯基砜因其生物学活性和合成用途而享有特权。合成转化以有效地获得具有这些基序的高价值化合物是人们所期望和追求的。在本文中，描述了一种新的方法，可通过药理学上普遍的甲基吡啶酰胺的吡啶环附近的C（sp 3）-H键与烯基砜1-甲基-4-（丙基）的选择性官能化来形成含乙烯基砜的化合物-1,2-二烯-1-基磺酰基）苯。反应条件温和，不需要金属催化剂或添加剂，并且显示出良好的官能团耐受性。对于这种异常转化的机理研究表明，该反应通过罕见的吡啶引发的p-甲苯磺酸根阴离子介导的烯丙基砜的活化，类似于膦触发的反应。
• Photoinduced Intramolecular Proton Transfer and Charge Redistribution in Imidazopyridines
  作者：Abderrazzak Douhal、Francisco Amat-Guerri、A. Ulises Acuna

  DOI：10.1021/j100001a014

  日期：1995.1

  The ground-state conformation and fluorescence properties of two closely related dyes 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine (1,2-HPIP) and 3-(2'-hydroxyphenyl)imidazo[1,5-a]pyridi (1,5-HPIP) have been studied in various solvents at room temperature to determine the origin of the large red-shifted emission spectra. The two compounds have a ground-state planar conformation stabilized by an intramolecular ii bond (MB) between the imino and phenol groups. On electronic excitation in cyclohexane solution a weak fluorescence is observed in the two dyes, with large Stokes shifts (1,2-HPIP: lambda(max) = 588 nm, Delta v = 11 000 cm(-1) 1,5-HPIP: lambda(max) 440 nm, Delta v = 9000 cm(-1)). For the first dye it is proposed that the emission takes place from a zwitterion produced by a proton-transfer reaction in the singlet manifold. A quinonoid, neutral phototautomer is excluded on the basis of the electronic structure of the molecule. In the case of 1,5-HPIP, the IHB is broken on electronic excitation and neither a proton nor H atom transfer occurs due to the reversal of the proton affinity of the imino group. The anomalous fluorescence is assigned to significant changes in the geometry of the emitting state following excitation.