(S)-1-hydroxyallyltrimethylsilane | 1233923-73-3

• 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-hydroxyallyltrimethylsilane
• 英文别名: (1S)-1-trimethylsilylprop-2-en-1-ol
• CAS: 1233923-73-3
• 化学式: C₆H₁₄OSi
• 分子量: 130.262
• InChiKey: BBLGXBVGDKCXQQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-1-(trimethylsilyl)allyl acetate 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 2.5h， 生成 (S)-1-hydroxyallyltrimethylsilane 、 (R)-1-hydroxyallyltrimethylsilane
  参考文献：
  名称：

  Enzymatic kinetic resolution of α-hydroxysilanes

  摘要：

  The enzymatic kinetic resolution of alpha-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various alpha-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active alpha-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.030

文献信息

• Stereoconvergent [1,2]- and [1,4]-Wittig Rearrangements of 2-Silyl-6-aryl-5,6-dihydropyrans: A Tale of Steric vs Electronic Regiocontrol of Divergent Pathways
  作者：Luis M. Mori-Quiroz、Robert E. Maleczka

  DOI：10.1021/jo5026942

  日期：2015.1.16

  The regiodivergent ring contraction of diastereomeric 2-silyl-5,6-dihydro-6-aryl-(2H)-pyrans via [1,2]- and [1,4]-Wittig rearrangements to the corresponding a-silylcyclopentenols or (alpha-cyclopropyl)acylsilanes favor the [1,4]-pathway by ortho and para directing groups in the aromatic appendage and/or by sterically demanding silyl groups. The [1,2]-pathway is dominant with meta directing or electron-poor aromatic moieties. Exclusive [1,2]-Wittig rearrangements are observed when olefin substituents proximal to the silyl are present. cis and trans diastereomers exhibit different reactivities, but converge to a single [1,2]- or [1,4]-Wittig product with high diastereoselectivity and yield.
• Enzymatic kinetic resolution of α-hydroxysilanes
  作者：Ilhwan An、Edith N. Onyeozili、Robert E. Maleczka

  DOI：10.1016/j.tetasy.2010.02.030

  日期：2010.3

  The enzymatic kinetic resolution of alpha-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various alpha-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active alpha-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees. (C) 2010 Elsevier Ltd. All rights reserved.