α-trimethylsilyl-1-octanol | 125828-07-1

• 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: α-trimethylsilyl-1-octanol
• 英文别名: 1-(trimethylsilyl)-1-octanol；1-Octanol, 1-(trimethylsilyl)-；1-trimethylsilyloctan-1-ol
• CAS: 125828-07-1
• 化学式: C₁₁H₂₆OSi
• 分子量: 202.412
• InChiKey: NXDKPBHBDMGJJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-trimethylsilyl-1-octanol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到1-(trimethylsilyl)-1-methoxyoctane
  参考文献：
  名称：

  Yoshida, Jun-Ichi; Maekawa, Tsuyoshi; Murata, Toshiki, Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1962 - 1970

  摘要：

  DOI：
• 作为产物：
  描述：

  α-((trimethylsilyl)oxy)octyltributylstannane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 α-trimethylsilyl-1-octanol
  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

• TBAHF₂ and TBAH₂F₃ as Activating Agents of Organosilanes
  作者：Atsunori Mori、Akinori Fujita、Kazutaka Ikegashira、Yasushi Nishihara、Tamejiro Hiyama

  DOI：10.1055/s-1997-3276

  日期：1997.6

  The fluoride reagents, TBAH2F3 and TBAHF2 (TBA: tetrabutylammonium), are found to catalyze the reactions of hexamethyldisilane with 1,3-dienes, aliphatic aldehydes, and aromatic aldehydes to give 1,4-disilyl-2-butenes, α-silyl alcohols and pinacols, respectively. Using an equimolar amount of TBAHF2 and disilanes, reduction of carbonyl compounds occurs in place of the silyl group addition.

  氟化剂TBAH2F3和TBAHF2（TBA：四丁基铵）被发现能够催化六甲基二硅烷与1,3-二烯、脂肪醛和芳香醛的反应，分别生成1,4-二硅基-2-丁烯、α-硅基醇和频哪醇。在使用等摩尔量的TBAHF2和二硅烷时，会发生羰基化合物的还原反应，取代硅基加成反应。
• A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols
  作者：Narayan G. Bhat、Amanda Garza

  DOI：10.1016/s0040-4039(03)01750-7

  日期：2003.9

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.
• Facile hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane–dioxane complex: An easy access to gem-dimetalloalkanes containing boron and silicon
  作者：Narayan G. Bhat、Mary A. Villanueva

  DOI：10.1016/j.jorganchem.2005.12.043

  日期：2006.3

  (Z)-l-Trimethylsilyl-l-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyi-l-alkynes followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in dichloromethane at 0 degrees C for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing alpha-trimethylsilyl group in 78-88% isolated yields. (c) 2006 Elsevier B.V. All rights reserved.
• LINDERMAN, RUSSELL J.;GHANNAM, AMEEN, J. AMER. CHEM. SOC., 112,(1990) N, C. 2392-2398
  作者：LINDERMAN, RUSSELL J.、GHANNAM, AMEEN

  DOI：——

  日期：——
• Synthetic utility and mechanistic studies of the aliphatic reverse Brook rearrangement
  作者：Russell J. Linderman、Ameen Ghannam

  DOI：10.1021/ja00162a048

  日期：1990.3