(S)-1-(dimethylphenylsilyl)-2-propen-1-ol | 1186614-95-8

• 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-(dimethylphenylsilyl)-2-propen-1-ol
• 英文别名: 2-Propen-1-ol, 1-(dimethylphenylsilyl)-, (1S)-；(1S)-1-[dimethyl(phenyl)silyl]prop-2-en-1-ol
• CAS: 1186614-95-8
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: KZWYPWCWHQYTQW-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  acetic acid (S)-1-(dimethylphenylsilyl)prop-2-enyl ester 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 2.5h， 以81%的产率得到(S)-1-(dimethylphenylsilyl)-2-propen-1-ol
  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

• Thermal rearrangements of .alpha.-(acyloxy)silanes: formation of chiral precursors and migratory preference of silicon-based groups
  作者：John D. Buynak、J. Byron Strickland、Grady W. Lamb、Dipti Khasnis、Seema Modi、Delena Williams、Hongming Zhang

  DOI：10.1021/jo00025a024

  日期：1991.12

  The asymmetric reduction of acylsilanes to chiral alpha-hydroxysilanes and the thermal rearrangement of the corresponding chiral alpha-acetoxysilanes was explored. IpcBCl reduces many acylsilanes in > 95% ee. The rate of the thermal rearrangement of the alpha-acetoxysilanes was dependent upon the substituents at both silicon and carbon. Evidence is presented to indicate there is electron deficiency at the alpha-carbon in the transition state. Migratory aptitudes follow those expected on the basis of the migrating group assuming an apical migratory group at a pentacoordinate silicon. A previously unreported hydrolytic transformation of a proposed acylsilyl hydride to a stable 1-sila-1,2-diol was observed.