1-(1R,5S)-6-Oxa-bicyclo[3.1.0]hex-1-yl-1-phenyl-ethanol | 83459-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-(1R,5S)-6-Oxa-bicyclo[3.1.0]hex-1-yl-1-phenyl-ethanol
• 英文别名: 1-[(1R,5S)-6-oxabicyclo[3.1.0]hexan-1-yl]-1-phenylethanol
• CAS: 83459-08-9
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: QPXHVFDIJPCWIP-IAMFDIQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1R,5S)-6-Oxa-bicyclo[3.1.0]hex-1-yl-1-phenyl-ethanol 在 ammonium hydroxide 、 氯化亚砜 、 18-冠醚-6 、 potassium tert-butylate 、 氯化铵 作用下， 以 异丙醇 为溶剂， 生成 (1R,2S)-2-Amino-1-(1-phenyl-vinyl)-cyclopentanol
  参考文献：
  名称：

  Synthesis applications of aza-cope rearrangements. Stereoselective synthesis of trans-alkyl-cis-3a-aryloctahydroindolones.

  摘要：

  DOI：

  10.1016/s0040-4039(00)87444-4
• 作为产物：
  描述：

  1-溴环戊-1-烯 、 苯乙酮 在 magnesium 、 间氯过氧苯甲酸 作用下， 生成 1-(1R,5S)-6-Oxa-bicyclo[3.1.0]hex-1-yl-1-phenyl-ethanol
  参考文献：
  名称：

  Synthesis applications of aza-cope rearrangements. Stereoselective synthesis of trans-alkyl-cis-3a-aryloctahydroindolones.

  摘要：

  DOI：

  10.1016/s0040-4039(00)87444-4

文献信息

• Stereoselective Reductive Rearrangement of α-Hydroxy Epoxides:  A New Method for Synthesis of 1,3-Diols¹
  作者：Yong Qiang Tu、Liang Dong Sun、Ping Zhen Wang

  DOI：10.1021/jo981097z

  日期：1999.1.1

  A novel and short synthetic method for the stereoselective synthesis of 1,3-diols has been developed by an unusual reductive rearrangement of a series of cl-hydroxy epoxides with aluminum isopropoxide. The reaction process was also investigated with deuterium-labeled aluminum isopropoxide, which revealed a site-specific 1,2-carbon-to-carbon migration and successive stereoselective hydride shift. The main synthetically valuable feature is that up to three contiguous carbon centers, the C-1, C-2, and C-3, were stereoselectively controlled with C-2 being quaternary. This reaction is of particular importance to the synthesis of newly developed powerful asymmetric hydrogenation catalysts containing the chiral ligands of spirocyclic diols.
• Synthesis applications of aza-cope rearrangements. Stereoselective synthesis of trans-alkyl-cis-3a-aryloctahydroindolones.
  作者：Larry E Overman、Leah T Mendelson、Lee A Flippin

  DOI：10.1016/s0040-4039(00)87444-4

  日期：——