tert-butyldimethylsilylether of trans-4-tert-butylcyclohexanol | 71009-16-0

• 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: tert-butyldimethylsilylether of trans-4-tert-butylcyclohexanol
• 英文别名: trans-4-tert-butylcyclohexyl tert-butyldimethylsilyl ether
• CAS: 71009-16-0
• 化学式: C₁₆H₃₄OSi
• 分子量: 270.531
• InChiKey: IAIGDQFCJXZEQF-HDJSIYSDSA-N

物化性质

• 沸点：
  248.0±8.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 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

• 作为反应物：
  描述：

  tert-butyldimethylsilylether of trans-4-tert-butylcyclohexanol 在 sulfonic acid functionalized nanoporous silica 作用下， 以 甲醇 为溶剂， 反应 3.2h， 以95%的产率得到trans-4-tert-Butylcyclohexanol
  参考文献：
  名称：

  A high loading sulfonic acid-functionalized ordered nanoporous silica as an efficient and recyclable catalyst for chemoselective deprotection of tert-butyldimethylsilyl ethers

  摘要：

  A high loading sulfonic acid-functionalized ordered nanoporous silica efficiently catalyzes the deprotection of a variety of alcoholic TBDMS (tert-butyldimethylsilyl)ethers in methanol. The catalyst shows high thermal stability (up to 240 degrees C) and can be recovered and reused for at least seven reaction cycles without loss of reactivity. This method can be used to deprotect TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.100
• 作为产物：
  描述：

  tert-butyl((4-(tert-butyl)cyclohex-1-en-1-yl)oxy)dimethylsilane 在 叔丁基过氧化氢 、 Mn(dpm)₃ 、 苯硅烷 、 calcium carbonate 作用下， 以 正己烷 、 异丙醇 为溶剂， 以211.0 mg的产率得到tert-butyldimethylsilylether of trans-4-tert-butylcyclohexanol
  参考文献：
  名称：

  Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol

  摘要：

  Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

  DOI：

  10.1021/ja412342g

文献信息

• Hydrosilylation of Carbonyl-Containing Substrates Catalyzed by an Electrophilic η¹-Silane Iridium(III) Complex
  作者：Sehoon Park、Maurice Brookhart

  DOI：10.1021/om100818y

  日期：2010.11.22

  Hydrosilation of a variety of ketones and aldehydes using the cationic iridium catalyst, (POCOP)Ir(H)(acetone)(+), 1, (POCOP = 2,6-bis(di-tert-butyl phosphinito)phenyl) is reported. With triethyl silane, all but exceptionally bulky ketones undergo quantitative reactions employing 0.5 mol% catalyst in 20-30 min at 25 degrees C. Hydrosilation of esters and amides results in over-reduction and cleavage

  报道了使用阳离子铱催化剂 (POCOP)Ir(H)(丙酮)(+), 1, (POCOP = 2,6-双(二叔丁基膦)苯基) 对各种酮和醛进行氢化硅烷化. 使用三乙基硅烷时，除特别大的酮外，所有酮类都会在 25 摄氏度、20-30 分钟内使用 0.5 mol% 的催化剂进行定量反应。酯和酰胺的氢化硅烷化分别导致 CO 和 CN 键的过度还原和断裂。4-叔丁基环己酮氢化硅烷化的非对映选择性已经使用多种硅烷进行了研究，并且高度依赖于温度。使用EtMe(2)SiH，分析顺式比例：作为温度函数的反式硅氢化产物为 DeltaDeltaH(double dagger) (DeltaH(double dagger) (trans) - DeltaH(double dagger) (cis)) 和 DeltaS(double dagger) (DeltaS(double dagger) (trans) - DeltaS(double
• Ionic Hydrogenation with Organosilanes under Acid-Free Conditions. Synthesis of Ethers, Alkoxysilanes, Thioethers, and Cyclic Ethers via rganosilyl Iodide and Triflate Catalyzed Reductions of Carbonyl Compounds and Their Derivatives
  作者：Mark B. Sassaman、G.K. Surya Prakash、George A. Olah、P. Donald、Katherine B. Loker

  DOI：10.1016/s0040-4020(01)86635-7

  日期：1988.1

  The general ether synthesis method based on the trialkylsilane/trialkylsilyl iodide or triflate reagent system has been extended to the syntheses of alkoxysilanes from ketones, tetrahydrofurans and tetrahydropyrans from dicarbonyl compounds, and thioethers by reductive cleavage of O-silylhemithioacetals.

  基于三烷基硅烷/三烷基甲硅烷基碘化物或三氟甲磺酸酯试剂系统的通用醚合成方法已扩展到由酮的烷氧基硅烷，由二羰基化合物的四氢呋喃和四氢吡喃以及硫醚通过O-甲硅烷基半硫缩醛的还原裂解而合成。
• Reductive cleavage of tert-butyldimethylsilyl ethers by diisobutylaluminum hydride
  作者：E. J. Corey、Graham B. Jones

  DOI：10.1021/jo00029a050

  日期：1992.1
• Tetrafluorosilane is a mild and very selective reagent for the cleavage of silyl-protected alcohols
  作者：E.J. Corey、Yi Kyu Yang

  DOI：10.1016/s0040-4039(00)74192-x

  日期：1992.4

  Silyl ethers are cleaved by SiF4 in CH2Cl2 or CH3CN at a rate which depends strongly on the steric screening of the ether oxygen, providing a promising method for selective desilylation under mild conditions.