1-hexan-1-ol | 125950-69-8

• 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: 1-hexan-1-ol
• 英文别名: (α-Hydroxyhexyl)allyldimethylsilane；(α-hydroxyethyl)dimethylallylsilane；1-(allyldimethylsilyl)-1-hexanol；1-[Dimethyl(prop-2-enyl)silyl]hexan-1-ol
• CAS: 125950-69-8
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: WWNZQMGOFXKAFK-UHFFFAOYSA-N

物化性质

• 沸点：
  260.9±15.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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-hexan-1-ol 在 4-二甲氨基吡啶 、 二甲基硫 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methoxyethyl 1-(dimethylmethoxysilyl)hexyl ether
  参考文献：
  名称：

  Highly Diastereoselective Intramolecular Allylation Reactions of Mixed Silyl-Substituted Acetals

  摘要：

  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.

  DOI：

  10.1021/jo9517048
• 作为产物：
  描述：

  α-((dimethylallylsilyl)oxy)hexyltributylstannane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 1-hexan-1-ol
  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.
• 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
• 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.