methyl 6-(triisopropylsilyloxy)hexanoate | 872620-26-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-(triisopropylsilyloxy)hexanoate
• 英文别名: Methyl 6-tri(propan-2-yl)silyloxyhexanoate；methyl 6-tri(propan-2-yl)silyloxyhexanoate
• CAS: 872620-26-3
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: DYQIQEVIDJZEJT-UHFFFAOYSA-N

物化性质

• 沸点：
  320.3±25.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-(triisopropylsilyloxy)hexanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以39%的产率得到6-(triisopropylsilyloxy)hexanoic acid
  参考文献：
  名称：

  Synthesis, Structure, and Reactivity of Unexpectedly Stable Spiroepoxy-β-Lactones Obtained by Epoxidation of 4-Alkylidene-2-Oxetanones

  摘要：

  We describe the first synthesis of spiroepoxy-beta-lactones obtained via epoxidation of ketene dimers. These compounds display unexpected stability that may be due to a double anomeric effect garnered from analysis of bond lengths by X-ray crystallography of one spirocycle in comparison to calculated bond lengths of related structures. These new strained intermediates display interesting reactivity leading to a butenolide, an alpha-hydroxyketone, a triol, an alpha-chloroketone, and an alpha-azidoketone.

  DOI：

  10.1021/ja053478h
• 作为产物：
  描述：

  triisopropyl(pent-4-en-1-yloxy)silane 在 1,10-菲罗啉 、 potassium tert-butylate 、 copper (I) acetate 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 methyl 6-(triisopropylsilyloxy)hexanoate
  参考文献：
  名称：

  Copper-Catalyzed Carboxylation of Alkylboranes with Carbon Dioxide: Formal Reductive Carboxylation of Terminal Alkenes

  摘要：

  Carboxylation of alkylboron compounds (alkyl-9-BBN) with CO2 proceeded in the presence of catalytic amounts of CuOAc/1,10-phenanthroline and a stoichiometric amount of (KOBu)-Bu-t. The alkylboranes are easily and widely available through the alkene hydroboration, and thus the overall process represents a reductive carboxylation of alkenes with CO2. The broad functional group compatibility and the inexpensiveness of the Cu/1,10-phenathoroline catalyst system are attractive features of this protocol.

  DOI：

  10.1021/ol103128x

文献信息

• Copper-Catalyzed Carboxylation of Alkylboranes with Carbon Dioxide: Formal Reductive Carboxylation of Terminal Alkenes
  作者：Hirohisa Ohmiya、Masahito Tanabe、Masaya Sawamura

  DOI：10.1021/ol103128x

  日期：2011.3.4

  Carboxylation of alkylboron compounds (alkyl-9-BBN) with CO2 proceeded in the presence of catalytic amounts of CuOAc/1,10-phenanthroline and a stoichiometric amount of (KOBu)-Bu-t. The alkylboranes are easily and widely available through the alkene hydroboration, and thus the overall process represents a reductive carboxylation of alkenes with CO2. The broad functional group compatibility and the inexpensiveness of the Cu/1,10-phenathoroline catalyst system are attractive features of this protocol.
• Synthesis, Structure, and Reactivity of Unexpectedly Stable Spiroepoxy-β-Lactones Obtained by Epoxidation of 4-Alkylidene-2-Oxetanones
  作者：Richard J. Duffy、Kay A. Morris、Daniel Romo

  DOI：10.1021/ja053478h

  日期：2005.12.1

  We describe the first synthesis of spiroepoxy-beta-lactones obtained via epoxidation of ketene dimers. These compounds display unexpected stability that may be due to a double anomeric effect garnered from analysis of bond lengths by X-ray crystallography of one spirocycle in comparison to calculated bond lengths of related structures. These new strained intermediates display interesting reactivity leading to a butenolide, an alpha-hydroxyketone, a triol, an alpha-chloroketone, and an alpha-azidoketone.