(S)-3-[6-(tert-butyldimethylsilyloxy)-2,7,8-trimethylchroman-2-yl]propan-1-ol | 1206474-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-3-[6-(tert-butyldimethylsilyloxy)-2,7,8-trimethylchroman-2-yl]propan-1-ol
• 英文别名: 3-[(2S)-6-[tert-butyl(dimethyl)silyl]oxy-2,7,8-trimethyl-3,4-dihydrochromen-2-yl]propan-1-ol
• CAS: 1206474-52-3
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: YCSUBILHTBNKFD-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-[6-(tert-butyldimethylsilyloxy)-2,7,8-trimethylchroman-2-yl]propan-1-ol 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3-(6-(tertbutyldimethylsilyloxy)-2,7,8-trimethylchroman-2-yl)propanal
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (S)-γ-CEHC [(S)-LLU-α]

  摘要：

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.

  DOI：

  10.1021/ol9027804
• 作为产物：
  描述：

  在 Ni Raney 作用下， 以 乙醇 为溶剂， 生成 (S)-3-[6-(tert-butyldimethylsilyloxy)-2,7,8-trimethylchroman-2-yl]propan-1-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (S)-γ-CEHC [(S)-LLU-α]

  摘要：

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.

  DOI：

  10.1021/ol9027804

文献信息

• Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (<i>S</i>)-γ-CEHC [(<i>S</i>)-LLU-α]
  作者：Mercedes Lecea、Gloria Hernández-Torres、Antonio Urbano、M. Carmen Carreño、Françoise Colobert

  DOI：10.1021/ol9027804

  日期：2010.2.5

  The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.