6-(tert-butyldimethylsilyloxy)-7,8-dimethylchroman-2-one | 1206474-46-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 6-(tert-butyldimethylsilyloxy)-7,8-dimethylchroman-2-one
• 英文别名: 6-[Tert-butyl(dimethyl)silyl]oxy-7,8-dimethyl-3,4-dihydrochromen-2-one
• CAS: 1206474-46-5
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: SQVHDKQANXZSEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(tert-butyldimethylsilyloxy)-7,8-dimethylchroman-2-one 、 (S)-(-)-甲基对甲苯亚砜 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以74%的产率得到(SS)-6-(tert-butyldimethylsilyloxy)-7,8-dimethyl-2-(p-tolylsulfinylmethyl)chroman-2-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
• 作为产物：
  描述：

  6-hydroxy-7,8-dimethylchroman-2-one 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以100%的产率得到6-(tert-butyldimethylsilyloxy)-7,8-dimethylchroman-2-one
  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.