6-(triisopropylsilyloxy)hexanoic acid | 872620-31-0

• 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: 6-(triisopropylsilyloxy)hexanoic acid
• 英文别名: 6-Tri(propan-2-yl)silyloxyhexanoic acid；6-tri(propan-2-yl)silyloxyhexanoic acid
• CAS: 872620-31-0
• 化学式: C₁₅H₃₂O₃Si
• 分子量: 288.503
• InChiKey: ZYFTUJAIQOGKLX-UHFFFAOYSA-N

物化性质

• 沸点：
  348.3±25.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(triisopropylsilyloxy)hexanoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 6-(triisopropylsilyloxy)hexanoyl chloride
  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：

  6-羟基己酸甲酯 在 咪唑 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 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

文献信息

• Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide
  作者：Francisco Juliá-Hernández、Toni Moragas、Josep Cornella、Ruben Martin

  DOI：10.1038/nature22316

  日期：2017.5

  along the hydrocarbon side-chain with excellent regio- and chemoselectivity, representing a remarkable reactivity relay when compared with classical cross-coupling reactions. Our results demonstrate that site-selectivity can be switched and controlled, enabling the functionalization of less-reactive positions in the presence of a priori more reactive ones. Furthermore, we show that raw materials obtained

  在组装复杂分子时，催化碳-碳键的形成可以简化合成路线。在加入饱和烃时尤为重要，饱和烃是石化产品和生物相关分子中的常见基序。然而，涉及烷基亲电试剂的交叉偶联方法仅在特定和先前功能化的位点导致催化键形成。在这里，我们描述了一种催化方法，该方法能够在大气压下用二氧化碳促进远程和未官能化脂肪族位点的羧化反应。该反应通过催化剂沿烃侧链的选择性迁移而发生，具有优异的区域选择性和化学选择性，与经典的交叉偶联反应相比，代表了显着的反应性中继。我们的结果表明，可以切换和控制位点选择性，从而在存在先验的更具反应性的位置的情况下实现反应性较低的位置的功能化。此外，我们表明从石油加工中大量获得的原材料，如烷烃和未精制的烯烃混合物，可以用作底物。这提供了一个机会，通过直接转化石油衍生的原料，将催化平台整合到有价值的脂肪酸中。
• Iron-catalyzed Aerobic Oxidation of Silyl Ethers to Carboxylic Acids
  作者：Zuizhi Lin、Shengming Ma

  DOI：10.1039/d4cc01234h

  日期：——

  Direct aerobic oxidation of silyl ethers to carboxylic acids has been developed. The mild reaction conditions lead to a broad range of functional group compatibility. Different types of silyl groups have been investigated and selective deprotective oxidation has been realized. The reaction could be conducted under air.

  已经开发出甲硅烷基醚直接有氧氧化成羧酸的方法。温和的反应条件导致广泛的官能团相容性。研究了不同类型的甲硅烷基并实现了选择性脱保护氧化。该反应可以在空气下进行。
• 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.