(S)-1-chloro-3-((triethylsilyl)oxy)propan-2-ol | 1373441-13-4

• 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: (S)-1-chloro-3-((triethylsilyl)oxy)propan-2-ol
• 英文别名: (S)-1-chloro-3-(triethylsilyloxy)propan-2-ol；(2S)-1-chloro-3-triethylsilyloxypropan-2-ol
• CAS: 1373441-13-4
• 化学式: C₉H₂₁ClO₂Si
• 分子量: 224.803
• InChiKey: TXBOFUHJVKEADS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• 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 、 3-氯-1,2-丙二醇 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 叔丁醇 为溶剂， 反应 1.25h， 以41%的产率得到(S)-1-chloro-3-((triethylsilyl)oxy)propan-2-ol
  参考文献：
  名称：

  Resolution of Terminal 1,2-Diols via Silyl Transfer

  摘要：

  Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of chemically differentiating a terminal 1,2-diol with concomitant resolution of the enantiomers.

  DOI：

  10.1021/jo4012909

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.
• Resolution of Terminal 1,2-Diols via Silyl Transfer
  作者：Xixi Sun、Amanda D. Worthy、Kian L. Tan

  DOI：10.1021/jo4012909

  日期：2013.10.18

  Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of chemically differentiating a terminal 1,2-diol with concomitant resolution of the enantiomers.