(E)-1-(2-thienyl)-3-phenyl-3-({[(E)-1-phenylethylidene]amino}oxy)-2-propen-1-one | 1246854-91-0

• 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: (E)-1-(2-thienyl)-3-phenyl-3-({[(E)-1-phenylethylidene]amino}oxy)-2-propen-1-one
• 英文别名: (E)-3-phenyl-3-[(E)-1-phenylethylideneamino]oxy-1-thiophen-2-ylprop-2-en-1-one
• CAS: 1246854-91-0
• 化学式: C₂₁H₁₇NO₂S
• 分子量: 347.437
• InChiKey: CHSTXCVMZWOFAX-RQRAPYSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-phenyl-1-(2-thienyl)-2-propyn-1-one 、 (E)-1-phenylethanone oxime 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以85%的产率得到(E)-1-(2-thienyl)-3-phenyl-3-({[(E)-1-phenylethylidene]amino}oxy)-2-propen-1-one
  参考文献：
  名称：

  Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes

  摘要：

  Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 degrees C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH2Cl2, rt, 7 h) to afford (E)-(O)-2-(acyl)vinylketoximes (92-98% stereoselectivity) in a yield of up to 85%. The (E)-adducts obtained are energetically less favorable than the corresponding (Z)-isomers and are gradually enriched with (Z)-isomers, thus indicating the kinetic control of (E)-stereoselectivity of the reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.057

文献信息

• Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes
  作者：Boris A. Trofimov、Tatyana E. Glotova、Marina Yu. Dvorko、Igor’ A. Ushakov、Elena Yu. Schmidt、Al’bina I. Mikhaleva

  DOI：10.1016/j.tet.2010.07.057

  日期：2010.9

  Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 degrees C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH2Cl2, rt, 7 h) to afford (E)-(O)-2-(acyl)vinylketoximes (92-98% stereoselectivity) in a yield of up to 85%. The (E)-adducts obtained are energetically less favorable than the corresponding (Z)-isomers and are gradually enriched with (Z)-isomers, thus indicating the kinetic control of (E)-stereoselectivity of the reaction. (C) 2010 Elsevier Ltd. All rights reserved.