(E)-N-(1-phenylethylidene)pyridin-2-amine | 120810-61-9

• 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: (E)-N-(1-phenylethylidene)pyridin-2-amine
• 英文别名: (E)-1-phenyl-N-pyridin-2-ylethanimine
• CAS: 120810-61-9
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: AYBLPWINLACVHO-RVDMUPIBSA-N

物化性质

• 沸点：
  303.2±24.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-(1-phenylethylidene)pyridin-2-amine 在 copper(l) iodide 、 氧气 作用下， 以 N-甲基吡咯烷酮 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 以15%的产率得到2-苯基咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles

  摘要：

  CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.

  DOI：

  10.1021/jo402134x
• 作为产物：
  描述：

  2-氨基吡啶 、 苯乙酮二乙酮 生成 (E)-N-(1-phenylethylidene)pyridin-2-amine
  参考文献：
  名称：

  Schmid; Bangler, Chemische Berichte, 1925, vol. 58, p. 1972

  摘要：

  DOI：

文献信息

• Pd-catalyzed carbonylative cycloamidation of ketoimines for the synthesis of pyrido[1,2-a]pyrimidin-4-ones
  作者：Ying Xie、Tengfei Chen、Shaomin Fu、Huanfeng Jiang、Wei Zeng

  DOI：10.1039/c5cc02631h

  日期：——

  The Pd(ii)-catalyzed pyridine-directed carbonylative cycloamidation of ketoimines has provided an efficient protocol for assembly of pyrido[1,2-a]pyrimidin-4-ones.

  Pd（II）催化的吡啶导向羰基环化肼酮的羰基化环酰胺化反应为合成吡啶并[1,2-a]嘧啶-4-酮提供了高效的方案。
• Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp³ C–H bond activation
  作者：Ying Xie、Tengfei Chen、Shaomin Fu、Xing-Shu Li、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1039/c4cc04676e

  日期：——

  The palladium-catalyzed oxidative [3+2] cycloaddition of ketoimines with alkynes provided an efficient access to multisubstituted pyrroles via Csp³–H activation.

  钯催化的酮亚胺与炔烃的氧化[3+2]环加成反应，通过Csp^3-H活化，有效地实现了对多取代吡咯的高效访问。
• Thiocarbonylation of C(sp3)-H bonds in pyridylamines with CS2: Facile synthesis of pyrido[1,2-a]pyrimidine-4-thiones
  作者：Xiao-Yu Zhou、Xiang-Yu Li、Zhen Zhang、Da-Gang Yu

  DOI：10.1016/j.cclet.2021.05.055

  日期：2021.12

  Herein, a facile synthesis of valuable pyrido[1,2-a]pyrimidine-4-thiones is reported via novel thiocarbonylation of C(sp3)-H bonds with carbon disulfide (CS2). This reaction features easy availability of substrates, good functional group tolerance, high yields, facile scalability and atom economy. Mechanistic investigations indicate that sulfate anion and sulfuric anhydride anion might be involved

  在此，通过C(sp 3 )-H 键与二硫化碳 (CS 2 ) 的新型硫代羰基化，报道了有价值的吡啶并[1,2 - a ]嘧啶-4-硫酮的简便合成。该反应具有底物容易获得、官能团耐受性好、产率高、易于扩展和原子经济等特点。机理研究表明，硫酸根阴离子和硫酸酐阴离子可能参与该反应。
• Gudasi; Nadagouda; Goudar, Journal of the Indian Chemical Society, 2006, vol. 83, # 4, p. 376 - 378
  作者：Gudasi、Nadagouda、Goudar

  DOI：——

  日期：——