2-<(E)-2-(N,N-dimethylamino)ethenyl>pyridine | 137475-72-0

• 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: 2-<(E)-2-(N,N-dimethylamino)ethenyl>pyridine
• 英文别名: (E)-2-(2-dimethylaminoethenyl)pyridine；2-[(E)-2-(N,N-dimethylamino)ethenyl]pyridine；Ethenamine, N,N-dimethyl-2-(2-pyridinyl)-, (1E)-；(E)-N,N-dimethyl-2-pyridin-2-ylethenamine
• CAS: 137475-72-0
• 化学式: C₉H₁₂N₂
• 分子量: 148.208
• InChiKey: RKBYFFZYJDNCQL-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苯基-5-噁唑酮 、 2-<(E)-2-(N,N-dimethylamino)ethenyl>pyridine 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 3-benzoylamino-4H-quinolizin-4-one
  参考文献：
  名称：

  Copar, Anton; Stanovnik, Branko; Tisler, Miha, Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 7, p. 533 - 538

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙烯基吡啶 、 二甲胺 在 [Rh(COD)(DPEphos)][BF4] 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 以79%的产率得到2-(2-二甲基氨基乙基)吡啶
  参考文献：
  名称：

  Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes

  摘要：

  The transition metal-catalyzed anti-Markovnikov hydroamination of unactivated vinylarenes with a rhodium complex of DPEphos is reported. The reaction of electron-neutral or electron-rich vinylarenes with a variety of secondary amines in the presence of catalyst forms the products from anti-Markovnikov hydroamination in high yields. Reactions of morpholine, N-phenylpiperazine, N-Boc-piperazine, piperidine, 2,5-dimethylmorpholine, and perhydroisoquinoline reacted with styrene to form the amine product in 51-71% yield. Reactions of a variety of vinylarenes with morpholine generated amine as the major product. Reactions of morpholine with electron-poor vinylarenes gave lower amine:enamine ratios than reactions of electron-rich vinylarenes at the same concentration of vinylarene, but conditions were developed with lower concentrations of electron-poor vinylarene to maintain formation of the amine as the major product. Reactions of dimethylamine with vinylarenes were fast and formed amine as the major product. Mechanistic studies on the hydroamination process showed that the amine:enamine ratio was lower for reactions conducted with higher concentrations of vinylarene and that one vinylarene influences the selectivity for reaction of another. A mechanism proceeding through a metallacyclic intermediate that opens in the presence of a second vinylarene accounts for these and other mechanistic observations.

  DOI：

  10.1021/ja0293608

文献信息

• CASSITY R. P.; TAYLOR L. T.; WOLFE J. F., J. ORG. CHEM., 1978, 43, NO 11, 2286-2288
  作者：CASSITY R. P.、 TAYLOR L. T.、 WOLFE J. F.

  DOI：——

  日期：——
• Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes
  作者：Masaru Utsunomiya、Ryoichi Kuwano、Motoi Kawatsura、John F. Hartwig

  DOI：10.1021/ja0293608

  日期：2003.5.1

  The transition metal-catalyzed anti-Markovnikov hydroamination of unactivated vinylarenes with a rhodium complex of DPEphos is reported. The reaction of electron-neutral or electron-rich vinylarenes with a variety of secondary amines in the presence of catalyst forms the products from anti-Markovnikov hydroamination in high yields. Reactions of morpholine, N-phenylpiperazine, N-Boc-piperazine, piperidine, 2,5-dimethylmorpholine, and perhydroisoquinoline reacted with styrene to form the amine product in 51-71% yield. Reactions of a variety of vinylarenes with morpholine generated amine as the major product. Reactions of morpholine with electron-poor vinylarenes gave lower amine:enamine ratios than reactions of electron-rich vinylarenes at the same concentration of vinylarene, but conditions were developed with lower concentrations of electron-poor vinylarene to maintain formation of the amine as the major product. Reactions of dimethylamine with vinylarenes were fast and formed amine as the major product. Mechanistic studies on the hydroamination process showed that the amine:enamine ratio was lower for reactions conducted with higher concentrations of vinylarene and that one vinylarene influences the selectivity for reaction of another. A mechanism proceeding through a metallacyclic intermediate that opens in the presence of a second vinylarene accounts for these and other mechanistic observations.
• Copar, Anton; Stanovnik, Branko; Tisler, Miha, Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 7, p. 533 - 538
  作者：Copar, Anton、Stanovnik, Branko、Tisler, Miha

  DOI：——

  日期：——