(1-hydroxy-2-methyl-2-propenyl)trimethylsilane | 99268-88-9

• 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: (1-hydroxy-2-methyl-2-propenyl)trimethylsilane
• 英文别名: 2-Methyl-1-trimethylsilylprop-2-en-1-ol
• CAS: 99268-88-9
• 化学式: C₇H₁₆OSi
• 分子量: 144.289
• InChiKey: CVLIHSLYWKSPSC-UHFFFAOYSA-N

物化性质

• 沸点：
  179.4±20.0 °C(Predicted)
• 密度：
  0.835±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-hydroxy-2-methyl-2-propenyl)trimethylsilane 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-methyl-1-trimethylsilylprop-2-en-1-one
  参考文献：
  名称：

  A practical and efficient synthesis of .alpha.,.beta.-unsaturated acylsilanes

  摘要：

  DOI：

  10.1021/jo00225a083
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-甲基-2-丙烯-1-醇 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以81%的产率得到(1-hydroxy-2-methyl-2-propenyl)trimethylsilane
  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.
• Oxygenated allylic silanes: useful homoenolate equivalents for the stereoselective C-glycosidation of pyranoside derivatives
  作者：James S. Panek、Michelle A. Sparks

  DOI：10.1021/jo00270a005

  日期：1989.4
• PANEK, J. S.;SPARKS, M. A., J. ORG. CHEM., 54,(1989) N, C. 2034-2038
  作者：PANEK, J. S.、SPARKS, M. A.

  DOI：——

  日期：——