(E)-2-(2-phenylethynyl)benzaldehyde O-benzyl-oxime | 1159003-32-3

• 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: (E)-2-(2-phenylethynyl)benzaldehyde O-benzyl-oxime
• CAS: 1159003-32-3
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: WVNOOPAMADCAMU-HAVVHWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-phenylethynyl)benzaldehyde O-benzyl-oxime 在 三氟甲磺酸 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以95%的产率得到3-苯基异喹啉
  参考文献：
  名称：

  AgOTf and TfOH co-catalyzed isoquinoline synthesis via redox reactions of O-alkyl oximes

  摘要：

  Under AgOTf and Bronsted acid co-catalysis, O-alkyl o-alkynylbenzaldoxime derivatives undergo a cyclization-induced N-O cleavage to produce isoquinolines with the simultaneous oxidation of O-alkyl group. This redox-based method provides a general access to diverse isoquinoline-derived heterocycles that are simple, efficient, and tolerant of various functional groups from readily available and hydrolytically stable oxime precursors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.144
• 作为产物：
  描述：

  溴甲苯 、 2-phenylethynylbenzaldehyde oxime 在 氢氧化钾 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以40%的产率得到(E)-2-(2-phenylethynyl)benzaldehyde O-benzyl-oxime
  参考文献：
  名称：

  AgOTf and TfOH co-catalyzed isoquinoline synthesis via redox reactions of O-alkyl oximes

  摘要：

  Under AgOTf and Bronsted acid co-catalysis, O-alkyl o-alkynylbenzaldoxime derivatives undergo a cyclization-induced N-O cleavage to produce isoquinolines with the simultaneous oxidation of O-alkyl group. This redox-based method provides a general access to diverse isoquinoline-derived heterocycles that are simple, efficient, and tolerant of various functional groups from readily available and hydrolytically stable oxime precursors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.144

文献信息

• A Dramatic Substituent Effect in Silver(I)-Catalyzed Regioselective Cyclization of ortho-Alkynylaryl Aldehyde Oxime Derivatives
  作者：Hongyin Gao、Junliang Zhang

  DOI：10.1002/adsc.200800568

  日期：2009.1

  A dramatic substituent effect was found in the silver(I)-catalyzed cyclization reaction of ortho-alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)-catalyzed reaction in dimethylacetamide at 110 °C (conditions A) affords isoquinolines in good to excellent yields, in contrast, isoquinolin-1(2 H)-ones were produced in moderate to high yields under conditions B (dimethylformamide

  在邻炔基芳基醛肟肟衍生物的银（I）催化的环化反应中发现了显着的取代作用。当R为烷基时，在110°C（条件A）下在二甲基乙酰胺中的Ag（I）催化反应以良好至极好的收率得到异喹啉，相反，异喹啉-1（2  H）-以中等至当R为乙酰基时，在条件B（二甲基甲酰胺，室温）下高收率。通过细微的结构修饰，为该产物选择性控制反应（PSCR）提出了合理的机制。