(-)-menthol trimethylsilyl ether | 18419-38-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-menthol trimethylsilyl ether
• 英文别名: (-)-O-[(1R,2S,5R)-2-isopropyl-5-methylcyclohex-1-yl]trimethylsilane；(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)trimethylsilane；{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}trimethylsilane；(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxytrimethylsilane；(-)-menthyloxytrimethylsilyl ether；(-)-menthyl trimethylsilyl ether；(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl trimethylsilyl ether；trimethyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxysilane
• CAS: 18419-38-0；62338-23-2；88390-70-9；122999-13-7；66808-39-7
• 化学式: C₁₃H₂₈OSi
• 分子量: 228.45
• InChiKey: LDWGJYAAQHHQTJ-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-menthol trimethylsilyl ether 在 1-butylpyridinium tetrachloroferrate(III) 、 pyridinium chlorochromate 作用下， 反应 0.33h， 以87%的产率得到(-)-薄荷酮
  参考文献：
  名称：

  Efficient and Convenient Procedure for Protection of Hydroxyl Groups to the THP, THF and TMS Ethers and Oxidation of these Ethers to their Aldehydes or Ketones in [BPy]FeCl₄ as a Low Cost Room Temperature Ionic Liquid

  摘要：

  醇类在1-丁基吡啶氯铁介质中被转化为相应的THP、THF或TMS醚，产率高至极好。这是一种稳定且低成本的室温离子液体。此外，在这种离子液体中，这些醚被氧化为它们的醛或酮，而没有发生任何过氧化反应。

  DOI：

  10.1515/znb-2006-0313
• 作为产物：
  描述：

  L-薄荷醇 、 六甲基二硅氮烷 在 aluminum hydrogen sulfate 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以95%的产率得到(-)-menthol trimethylsilyl ether
  参考文献：
  名称：

  Silylation and Tetrahydropyranylation of Alcohols Catalyzed by Al(HSO₄)₃

  摘要：

  醇的特戊酰化和四氢吡喃化反应在Al(HSO4)3的高效催化下进行，所有反应均在温和且完全非均相的条件下进行，产率良好至高。

  DOI：

  10.1246/bcsj.78.1982
• 作为试剂：
  描述：

  甲醇 、 异戊醛 在 lithium perchlorate 、 (-)-menthol trimethylsilyl ether 、 三氟乙酸 作用下， 反应 2.0h， 以29%的产率得到(3R,4S)-3-methoxymethyl-2,6-dimethylheptan-4-ol
  参考文献：
  名称：

  Asymmetric Acid-Catalyzed Meerwein−Ponndorf−Verley−Aldol Reactions of Enolizable Aldehydes

  摘要：

  A highly, stereo- and regioselective Meerwein - Ponndorf - Verley - Aldol etherification process of enolizable aldehydes is described. This new transformation is catalyzed by trifluoroacetic acid. The method also allows cross-aldol reactions with alpha-branched enolizable aldehydes and thus provides access to defined configured quaternary stereogenic centers.

  DOI：

  10.1021/ol100093u

文献信息

• Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar

  DOI：10.1016/j.crci.2013.01.018

  日期：2014.2

  eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively

  摘要 以稻壳 (RiH) 为原料，开发了一种温和、高效、环保的方案，用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点，可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外，
• Silylation of Alcohols and Phenols Using Hexamethyldisilazane Catalyzed by <i>N,N</i>’-Diiodo-<i>N,N</i>’-1,2-ethanediyl Bis(<i>p</i>-toluenesulfonamide) Under Solvent-Free and Microwave Conditions
  作者：Ramin Ghorbani-Vaghei、Seyedeh Mina Malaekehpoor

  DOI：10.1080/10426500902849581

  日期：2010.2.23

  N,N′-Diiodo-N,N′-1,2-ethanediyl bis(p-toluenesulfonamide) (NIBTS) is an effective catalyst for the silylation of alcohols and phenols using hexamethyldisilazane under solvent-free and microwave conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  N,N'-Diiodo-N,N'-1,2-乙二基双（对甲苯磺酰胺）（NIBTS）是在无溶剂和微波条件下使用六甲基二硅氮烷对醇和酚进行硅烷化的有效催化剂。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。
• Zinc Mediated Reactions in Organic Synthesis: Efficient Synthesis of Silyl Ethers under Mild Conditions
  作者：Babasaheb Pandurang Bandgar、Satish Navnath Chavare、Shivaji Sandu Pandit

  DOI：10.1002/jccs.200500019

  日期：2005.2

  General and practical method for the synthesis of silyl ethers in the presence of zinc powder under mild conditions has been described.

  描述了在温和条件下在锌粉存在下合成甲硅烷基醚的一般实用方法。
• Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispread in silica gel under neutral condition
  作者：Najmedin Azizi、Rozbeh Yousefi、Mohammad R. Saidi

  DOI：10.1016/j.jorganchem.2005.11.005

  日期：2006.2

  for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols with hexamethyldisilazane on the surface of silica gel dispersed with LiClO4 in room temperature at few minutes in excellent yields under neutral conditions is reported. This procedure also allows the excellent selectivity under LP-SiO2 system for silylation

  在室温下几分钟内，用六甲基二硅氮烷在六氯二硅氮烷上分散含有LiClO 4的硅胶表面上的多种醇，包括伯，烯丙基，苄基，仲，受阻仲，叔和苯酚的三甲基甲硅烷基化反应，非常高效，温和据报道在中性条件下产量极高。该方法还允许在存在胺和酚羟基的情况下在LP-SiO 2系统下对醇进行甲硅烷基化具有优异的选择性。
• Efficient Trimethylsilylation and Tetrahydropyranylation of Alcohols in the Presence of 1,3-Dibromo-5,5-dimethylhydantoin
  作者：Farhad Shirini、Mohammad Zolfigol、Maryam Paktinat

  DOI：10.1055/s-2006-950350

  日期：——

  Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditions in excellent yields.

  在1,3-二溴-5,5-二甲基海因（DBH）存在下，苯甲位以及一级和二级脂族醇的化学选择性三甲基硅烷化和四氢吡喃化反应在温和且完全非均相的反应条件下高效进行，产率极佳。