1-[二甲基(苯基)甲硅烷基]己烷-1-醇 | 125950-71-2

• 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
• 中文名称: 1-[二甲基(苯基)甲硅烷基]己烷-1-醇
• 英文名称: dimethylphenyl(α-hydroxyhexyl)silane
• 英文别名: 1-[(dimethyl)phenylsilyl]-1-hexanol；1-(dimethylphenylsilyl)-1-hexanol；1-(dimethylphenylsilyl)hexan-1-ol；1-(dimethylphenylsily)-1-hexanol；1-[Dimethyl(phenyl)silyl]hexan-1-OL
• CAS: 125950-71-2
• 化学式: C₁₄H₂₄OSi
• 分子量: 236.429
• InChiKey: QVVWPBWNZBIPHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-[二甲基(苯基)甲硅烷基]己烷-1-醇 在 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到1-氯己基二甲基苯基硅烷
  参考文献：
  名称：

  Stereoselective alkene synthesis via (.alpha.-chloroalkyl)(dimethyl)phenylsilanes and .alpha.-(dimethyl)phenylsilyl ketones

  摘要：

  DOI：

  10.1021/jo00027a069
• 作为产物：
  描述：

  α-((dimethylphenylsilyl)oxy)hexyltributylstannane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 1-[二甲基(苯基)甲硅烷基]己烷-1-醇
  参考文献：
  名称：

  Synthetic utility and mechanistic studies of the aliphatic reverse Brook rearrangement

  摘要：

  DOI：

  10.1021/ja00162a048

文献信息

• A direct conversion of (α-hydroxyalkyl)silanes to carboxylic acids
  作者：Russell J. Linderman、Kangyi Chen

  DOI：10.1016/s0040-4039(00)61771-9

  日期：1992.11

  (alpha-hydroxyalkyl)trialkylsilanes and acylsilanes are readily oxidized to the corresponding carboxylic acid using ozone.
• 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.
• Highly Diastereoselective Intramolecular Allylation Reactions of Mixed Silyl-Substituted Acetals
  作者：Russell J. Linderman、Kangyi Chen

  DOI：10.1021/jo9517048

  日期：1996.1.1

  The reaction of preformed mixed acetals derived from (alpha-hydroxyalkyl)dimethylallylsilane with a number of aromatic and aliphatic aldehydes in the presence of Lewis acids results in a highly diastereoselective intramolecular allylation reaction. The reaction proceeds through a cyclic synclinal S-E' addition of the allylsilane to an intermediate oxocarbenium ion. The reaction occurs exclusively by an intramolecular process as determined by means of a cross-over experiment. The relative stereochemistry was determined by the conversion of one of the allylation products to a known (stereodefined) aldol-type product. A greater degree of diastereoselectivity is obtained by in-situ formation of an oxocarbenium ion from (alpha-hydroxyhexyl)dimethylallylsilane and an aldehyde in the presence of boron trifluoride etherate. The diastereoselectivity of the in-situ allylation reaction typically exceeds 100:1 in favor of the syn adduct. However, reactions with electron rich aryl aldehydes resulted in a diminished degree of diastereoselectivity. The initial product of the in-situ reaction is an unstable silyl fluoride which is readily hydrolyzed to a silanol derivative upon reaction with methanolic potassium hydroxide. The overall yield of the two-step process is greater than 80%. A method for the synthesis of more highly substituted (alpha-alkoxyalkyl)dimethylallylsilanes by allyl anion displacement of methoxide from silicon is also described. The methyl siloxane derivatives were obtained by ozonolytic cleavage of an unsubstituted allyl group in methanol.
• A SIMPLE METHOD FOR MILD OXIDATION OF α-HYDROXYSILANES TO PROVIDE AROYLSILANES
  作者：Amauri F. Patrocínio、Paulo J. S. Moran

  DOI：10.1081/scc-100105124

  日期：2001.1

  Potassium permanganate supported onto alumina in hexane-water is a good oxidizing agent to convert alpha -hydroxysilanes into acylsilanes. This mild oxidation afforded aroylsilanes having electron-donating groups attached to the aromatic ring, in 70-86% yield.
• The synthesis of α-stannyl-silanes and their use in the formation of alkenes
  作者：Anthony G.M. Barrett、Jason M. Hill

  DOI：10.1016/s0040-4039(00)92687-x

  日期：1991.7

  alpha-Stannyl-silanes were prepared from aldehydes via alpha-hydroxy- and alpha-chloro-silanes. Stannyl-silane 5d was transmetallated using non-butylithium and the resultant alpha-lithio-silane condensed with aldehydes to yield alkenes.