4-phenyl-4-(prop-2-ynylamino)but-3-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-phenyl-4-(prop-2-ynylamino)but-3-en-2-one
• 英文别名: (Z)-4-phenyl-4-(prop-2-ynylamino)but-3-en-2-one
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: FXXMEWFEVCMCAH-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-4-(prop-2-ynylamino)but-3-en-2-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 碳酸氢钠 、 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.17h， 生成 1-(4-(4-fluorophenyl)-5-iodo-2-phenylpyridin-3-yl)ethanone
  参考文献：
  名称：

  Facile synthesis of iodopyridines from N-propargylic β-enaminones via iodine-mediated electrophilic cyclization

  摘要：

  A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic beta-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization has been found to be general for a broad range of N-propargylic beta-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The starting N-propargylic beta-enaminones have been prepared by conjugate addition of propargylamine to alpha,beta-allcynic ketones, followed by Sonogashira coupling with aryl iodides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.070
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.0h， 生成 4-phenyl-4-(prop-2-ynylamino)but-3-en-2-one
  参考文献：
  名称：

  Facile synthesis of iodopyridines from N-propargylic β-enaminones via iodine-mediated electrophilic cyclization

  摘要：

  A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic beta-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization has been found to be general for a broad range of N-propargylic beta-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The starting N-propargylic beta-enaminones have been prepared by conjugate addition of propargylamine to alpha,beta-allcynic ketones, followed by Sonogashira coupling with aryl iodides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.070

文献信息

• Vasil'eva,E.V. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, # 2, p. 306 - 309
  作者：Vasil'eva,E.V. et al.

  DOI：——

  日期：——
• Facile synthesis of iodopyridines from N-propargylic β-enaminones via iodine-mediated electrophilic cyclization
  作者：Sedef Karabiyikoglu、Yilmaz Kelgokmen、Metin Zora

  DOI：10.1016/j.tet.2015.04.070

  日期：2015.6

  A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic beta-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization has been found to be general for a broad range of N-propargylic beta-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The starting N-propargylic beta-enaminones have been prepared by conjugate addition of propargylamine to alpha,beta-allcynic ketones, followed by Sonogashira coupling with aryl iodides. (C) 2015 Elsevier Ltd. All rights reserved.