(E)-1-(-2-phenyl-1-(phenylethynyl)cyclopropyl)ethan-1-one O-methyl oxime | 1387605-55-1

• 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)-1-(-2-phenyl-1-(phenylethynyl)cyclopropyl)ethan-1-one O-methyl oxime
• 英文别名: (E)-1-(2-phenyl-1-(phenylethynyl)cyclopropyl)ethanone O-methyl oxime
• CAS: 1387605-55-1
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: BLOUUVTULJBMCX-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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)-1-(-2-phenyl-1-(phenylethynyl)cyclopropyl)ethan-1-one O-methyl oxime 、 苯甲醇 在 (tricyclohexylphosphine)gold(I) chloride 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 4.5h， 以87%的产率得到1-Methoxy-2-methyl-5-phenyl-3-(2-phenyl-2-phenylmethoxyethyl)pyrrole
  参考文献：
  名称：

  Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles

  摘要：

  A gold(I)-catalyzed tandem reaction of 1-(1-alkynyl) cyclopropyl oxime ethers with nucleophiles under mild conditions has been developed, which provides a facile access to highly substituted pyrroles in moderate to excellent yields.

  DOI：

  10.1055/s-0031-1290978
• 作为产物：
  描述：

  1-(2-phenyl-1-(phenylethynyl)cyclopropyl)ethanone 、 甲氧基胺盐酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以95%的产率得到(E)-1-(-2-phenyl-1-(phenylethynyl)cyclopropyl)ethan-1-one O-methyl oxime
  参考文献：
  名称：

  Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles

  摘要：

  A gold(I)-catalyzed tandem reaction of 1-(1-alkynyl) cyclopropyl oxime ethers with nucleophiles under mild conditions has been developed, which provides a facile access to highly substituted pyrroles in moderate to excellent yields.

  DOI：

  10.1055/s-0031-1290978

文献信息

• Pd(II)-Catalyzed Tandem Heterocyclization of 1-(1-Alkynyl)cyclopropyl Oxime Derivatives for the Synthesis of Functionalized Pyrroles
  作者：Dong Pan、Yin Wei、Min Shi

  DOI：10.1021/acs.orglett.6b02068

  日期：2016.8.5

  An efficient approach for the synthesis of highly functionalized pyrroles has been developed by a Pd(TFA)2-catalyzed tandem heterocyclization of 1-(1-alkynyl)cyclopropyl oxime derivatives under mild conditions. The reaction first proceeded via an intramolecular nucleophilic attack followed by a ring-opening process and then intermolecular nucleophilic attack as well as protonation to afford the desired

  通过在温和条件下Pd（TFA）2催化1-（1-炔基）环丙基肟衍生物的串联杂环化反应，已经开发出一种高效合成高度官能化吡咯的有效方法。该反应首先通过分子内亲核进攻，然后是开环过程，然后是分子间亲核进攻以及质子化进行，以中等至极好的收率提供所需的产物。