(1S)-1-cyclohexyl-2-triethylsilyloxyethanol | 211044-57-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S)-1-cyclohexyl-2-triethylsilyloxyethanol
• CAS: 211044-57-4
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: DFVBHXFGOSVGJL-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三乙基氯硅烷 、 (S)-1-cyclohexyl-1,2-ethanediol 在 (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine 、 N,N-二异丙基乙胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 0.67h， 以9%的产率得到(S)-5-cyclohexyl-3,3,8,8-tetraethyl-4,7-dioxa-3,8-disiladecane
  参考文献：
  名称：

  Site-Selective Catalysis: Toward a Regiodivergent Resolution of 1,2-Diols

  摘要：

  This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.

  DOI：

  10.1021/ja3027086

文献信息

• Site-Selective Catalysis: Toward a Regiodivergent Resolution of 1,2-Diols
  作者：Amanda D. Worthy、Xixi Sun、Kian L. Tan

  DOI：10.1021/ja3027086

  日期：2012.5.2

  This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.