(S)-2-phenyl-5-methoxy-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan | 1252832-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: (S)-2-phenyl-5-methoxy-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan
• 英文别名: (5S)-5-methoxy-2-phenyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan
• CAS: 1252832-62-4
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: SWYKTUDDGULYDW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 1-phenylethynyl-bicyclo[4.1.0]heptan-2-one 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以63%的产率得到(S)-2-phenyl-5-methoxy-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan
  参考文献：
  名称：

  Stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles

  摘要：

  The stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles was investigated. The substrates were prepared in non-racemic form (up to 88% ee) through parallel kinetic resolution (CBS reduction) and reoxidation of the separated diastereomeric alcohols. The key Au-catalyzed reaction was then found to proceed without significant loss of absolute stereochemical information: this way, an achiral carbocationic intermediate could be excluded. Thus, a bicyclobutonium-type intermediate seems to be attacked in a S(N)2-type fashion by the nucleophile in accordance with computational predictions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.019

文献信息

• Stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles
  作者：Stephan Labsch、Shute Ye、Andreas Adler、Jörg-Martin Neudörfl、Hans-Günther Schmalz

  DOI：10.1016/j.tetasy.2010.05.019

  日期：2010.7

  The stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles was investigated. The substrates were prepared in non-racemic form (up to 88% ee) through parallel kinetic resolution (CBS reduction) and reoxidation of the separated diastereomeric alcohols. The key Au-catalyzed reaction was then found to proceed without significant loss of absolute stereochemical information: this way, an achiral carbocationic intermediate could be excluded. Thus, a bicyclobutonium-type intermediate seems to be attacked in a S(N)2-type fashion by the nucleophile in accordance with computational predictions. (C) 2010 Elsevier Ltd. All rights reserved.