(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxytrimethylsilane

• 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: (1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxytrimethylsilane
• 英文别名: l-menthol trimethylsilyl ether；(+)-menthyl TMS-ether；trimethyl-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxysilane
• 化学式: C₁₃H₂₈OSi
• 分子量: 228.45
• InChiKey: LDWGJYAAQHHQTJ-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  D-薄荷醇 在 12-tungstophosphoric acid immobilized on [bmim][FeCl₄] 作用下， 反应 0.09h， 生成 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxytrimethylsilane
  参考文献：
  名称：

  H3PW12O40@[bmim][FeCl4]: A green catalytic system for alkoxymethylation of alcohols and their one-pot interconversion to acetates and TMS-ethers

  摘要：

  12-Tungstophosphoric acid immobilized on [bmim][FeCl4] was found to be an efficient catalyst for chemoselective methoxymethylation and ethxoymethylation of alcohols and also one-pot conversion of MOM- or EOM-ethers to their corresponding acetates and TMS-ethers under thermal conditions and microwave irradiation. These procedures were simple, rapid and the corresponding products were obtained in high yields. The catalyst exhibited remarkable reactivity and was reusable.

  DOI：

  10.1007/bf03249085
• 作为试剂：
  描述：

  2-甲基丁醛 在 4-二甲氨基吡啶 、 lithium perchlorate 、 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxytrimethylsilane 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (4S,5R)-5-(methoxymethyl)-2,5-dimethylheptan-4-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers

  摘要：

  A novel asymmetric aldol-reduction-etherification process of aliphatic enolizable aldehydes is described. The intermediately formed aldol adducts-beta-hydroxyaldehydes-were reduced and transformed into the corresponding 1,3-diol ethers by external secondary alcohols at the same time. Thus, with the help of chiral secondary alcohols an access to optically active 1,3-diol ether is given. Furthermore, asymmetric cross-aldol-Meerwein-Ponndorf reactions of enolizable aldehydes can also be realized under these reaction conditions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.069

文献信息

• Microwave-assisted rapid and efficient deprotection and direct esterification and silylation of MOM and EOM ethers catalyzed by [Hmim][HSO4] as a Brønsted acidic ionic liquid
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Ahmad Reza Khosropour、Arsalan Mirjafari

  DOI：10.1007/s00706-010-0373-6

  日期：2010.10

  Abstract1-Methylimidazolium hydrogensulfate, [Hmim][HSO4], a Brønsted acidic room temperature ionic liquid, is used as a catalyst and reaction medium for facile and eco-friendly deprotection of methoxymethyl (MOM) and ethoxymethyl (EOM) ethers to their corresponding alcohols under thermal conditions (Δ) and microwave irradiation (MW). Furthermore, one-pot interconversion to the respective acetates and

  摘要布朗斯台德酸性室温离子液体1-甲基咪唑硫酸氢盐[Hmim] [HSO 4 ]被用作催化剂和反应介质，可对甲氧基甲基（MOM）和乙氧基甲基（EOM）醚进行简便且环保的脱保护醇在热条件（Δ）和微波辐射（MW）下。此外，还实现了一锅转化为各自的乙酸酯和三甲基甲硅烷基（TMS）醚。 图形概要
• Silylation of Relatively Acidic Compounds with Alkyl Trimethylsilylacetates
  作者：Eiichi Nakamura、Koichi Hashimoto、Isao Kuwajima

  DOI：10.1246/bcsj.54.805

  日期：1981.3

  Silylation of ketones, alcohols, alkanethiols, phenols, and carboxylic acids with alkyl trimethylsilylacetates has been described from synthetic and mechanistic points of view.

  已从合成和机理的角度描述了用烷基三甲基硅基乙酸酯对酮、醇、烷基硫醇、酚和羧酸进行硅基化的过程。
• High-Yielding and Rapid Carbon-Carbon Bond Formation from Alcohols: Allylation by Means of TiCl4
  作者：Alfred Hassner、Chennakesava Bandi

  DOI：10.1055/s-0033-1338746

  日期：——

  TiCl4 efficiently promotes high yield (80–99%) replacement of OH in tertiary, benzylic, and allylic alcohols, and even nonactivated secondary alcohols, by an allyl group. The reaction usually proceeds within minutes at room temperature.

  TiCl4 有效地促进了烯丙基对叔醇、苄醇和烯丙醇，甚至未活化的仲醇中 OH 的高产率 (80-99%) 置换。反应通常在室温下在几分钟内进行。
• Unusual o-alkylation with iodomethyltrimethylsilane
  作者：T. K. Chakraborty、G. V. Reddy

  DOI：10.1039/c39890000251

  日期：——

  Iodomethyltrimethylsilane alkylates alkoxide ions giving rise to O-methyl and O-trimethylsilyl ethers which are formed by cleavage of the silicon–carbon bond.

  碘甲基三甲基硅烷烷基化烷氧基离子，生成O-甲基和O-三甲基甲硅烷基醚，它们是通过硅碳键断裂形成的。
• Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
  作者：Marjan Jereb

  DOI：10.1016/j.tet.2012.03.040

  日期：2012.5

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.