1-Trimethylsilyloxy-2-cyclohexylethane

• 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-Trimethylsilyloxy-2-cyclohexylethane
• 英文别名: 2-cyclohexylethoxy(trimethyl)silane
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: FVLNTTAINSRHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  1-Trimethylsilyloxy-2-cyclohexylethane 在 氨基磺酸 、 水 作用下， 反应 3.5h， 以85%的产率得到2-环己基乙醇
  参考文献：
  名称：

  Green and Efficient Procedure for the Trimethylsilylation of Hydroxy Groups and Their Regeneration Using Sulfamic Acid as Recyclable Catalyst

  摘要：

  Structurally diverse alcohols and phenols were efficiently transformed into their corresponding trimethylsilyl ethers with hexamethyldisilazane (HMDS) in the presence of catalytic amounts of sulfamic acid (SA) at room temperature under both acetonitrile and solvent-free conditions. Deprotection of these trimethylsilyl ethers to their parent alcohols and phenols was also achieved using this catalyst in water at room temperature.

  DOI：

  10.1080/00397910903097344
• 作为产物：
  描述：

  2-环己基乙醇 、 六甲基二硅氮烷 在 1,3-二溴-5,5-二甲基海因 作用下， 以 二氯甲烷 为溶剂， 反应 2.1h， 以95%的产率得到1-Trimethylsilyloxy-2-cyclohexylethane
  参考文献：
  名称：

  在催化量 1,3-Dibromo-5,5-Dimethylhydantoin (DBDMH) 的存在下，使用 HMDS 对醇和酚进行有效的三甲基甲硅烷基化，作为一种安全且廉价的工业化学品

  摘要：

  1,3-二溴-5,5-二甲基乙内酰脲 (DBDMH) 被发现是在室温下在二氯甲烷中用六甲基二硅氮烷 (HMDS) 三甲基硅烷化各种醇和酚的有效催化剂。

  DOI：

  10.1002/jccs.200700068

文献信息

• 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。
• Trimethylsilyl Protection of Alcohols Over Phosphorus Pentoxide Supported on Silica Gel
  作者：Hamid Reza Shaterian、Nafiseh Fahimi、Kobra Azizi

  DOI：10.1080/10426507.2010.526670

  日期：2011.7.1

  Abstract An eco-friendly and mild protocol for trimethylsilyl protection of alcohols over phosphorus pentoxide supported on silica gel using hexamethyldisilazane has been described. Solvent-free and ambient reaction conditions, easy workup, short reaction times, excellent yields, and reusability of the catalyst are the noticeable features of this methodology. GRAPHICAL ABSTRACT

  摘要描述了使用六甲基二硅氮烷在硅胶上负载五氧化二磷上对醇进行三甲基甲硅烷基保护的环保和温和的协议。该方法的显着特点是无溶剂和环境反应条件、易于处理、反应时间短、收率高、催化剂可重复使用。图形概要
• CONVENIENT TREMETHYLSILYLATION OF HYDROXY GROUPS WITH HEXAMETHYLDISILAZANE UNDER SOLVENT-FREE CONDITIONS
  作者：Amin Rostami、Ardeshir Khazaei、Marjan Mahboubifar、Sadegh Rahmati

  DOI：10.1080/00304940809458091

  日期：2008.6

  phenols), under essentially neutral conditions, prompted us to develop an efficient, convenient, and practical procedure for the protection of hydroxyI groups under solvent-free conditions. In continuation of our interest in the application of N-bromo compounds in organic synthesis,13 we now report the use of readily available HMDS for trimethylsilylation of alcohols and phenols in the presence catalytic

  有机合成中经常需要对羟基进行保护，其中一种常用的方法是转化为相应的甲硅烷基醚。有几种方法可用于羟基的甲硅烷基化。] 1,1,1,3,3,3-六甲基二硅氮烷 (HMDS) 易于将醇、酸、胺、硫醇、酚、酰胺、硫代酰胺、磺酰胺和可烯醇化酮进行甲硅烷基化；反应的副产物氨很容易从反应介质中除去。然而，HMDS 的低硅烷化能力是其使用的主要缺点，因此各种催化剂如 (CH,),SiCl? 氯化锌，? 锆磺基苯基P K-10 蒙脱石？1, : LiClO,? H,PW,,O,,R Al(OTf),? CuSO,~5H,0,'o 和 1,3-二溴-5,5-二甲基乙内酰脲 (DBH)”已用于激活该试剂。由于不同的原因，无溶剂反应在化学过程中引起了相当大的关注。从环境安全和经济角度来看，它们是有价值的，因为后处理容易、产品收率高且反应时间通常很快。 I2 缺乏用于羟基（醇类）三甲基甲硅烷基化的简便通用方法和酚）
• Heterogeneous Thiocyanation of Benzylic Alcohols and Silyl and THP Ethers, and Deprotection of Silyl and THP-Ethers by [PCl_3-n(SiO₂)_n] (Silphos)
  作者：N. Iranpoor、H. Firouzabadi、H. Bahador、A. Jamalian

  DOI：10.1080/10426500903419145

  日期：2010.8.25

  Silicaphosphite (silphos), [PCl3-n(SiO2)n], as a heterogeneous phosphorous compound, catalyzes the thiocyanation of benzylic alcohols and silyl and THP ethers in the presence of I2 and NH4SCN in refluxing CH3CN. The produced silphos oxide byproduct can be easily separated by a simple filtration. Silphos is also used for the efficient and selective deprotection of silyl and THP-ethers to their corresponding alcohols.
• Efficient Trimethylsilylation of Alcohols and Phenols with HMDS in the Presence of a Catalytic Amount of 1,3-Dibromo-5,5-Dimethylhydantoin (DBDMH) as a Safe and Cheap Industrial Chemical
  作者：Ardeshir Khazaei、Amin Rostami、Marjan Mahboubifar

  DOI：10.1002/jccs.200700068

  日期：2007.4

  1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) is found to be an effective catalyst for trimethylsilylation various alcohols and phenols with hexamethyldisilazane (HMDS) in dichloromethane at room temperature.

  1,3-二溴-5,5-二甲基乙内酰脲 (DBDMH) 被发现是在室温下在二氯甲烷中用六甲基二硅氮烷 (HMDS) 三甲基硅烷化各种醇和酚的有效催化剂。