{[tert-butyl-(diphenyl)silyl]oxy}cyclohexane | 75031-68-4

• 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-butyl-(diphenyl)silyl]oxy}cyclohexane
• 英文别名: cyclohexoxy-tert-butyldiphenylsilane；Tert-butyl-cyclohexyloxy-diphenylsilane
• CAS: 75031-68-4
• 化学式: C₂₂H₃₀OSi
• 分子量: 338.565
• InChiKey: DQYPUIKMYLJDLF-UHFFFAOYSA-N

物化性质

• 沸点：
  393.3±15.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 六甲基磷酰三胺 、 正丁基锂 、 偶氮二异丁腈 、 Celite 、 三氟化硼乙醚 、 三正丁基氢锡 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 4.5h， 生成 {[tert-butyl-(diphenyl)silyl]oxy}cyclohexane
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302

文献信息

• A mild method for rapid tert-butyldiphenylsilylation of primary and secondary alcohols
  作者：Steven A. Hardinger、Ngadi Wijaya

  DOI：10.1016/s0040-4039(00)79237-9

  日期：1993.6

  A rapid and efficient method for the protection of primary and secondary alcohols as their tert-butyldiphenylsilyl (tBDPS) ethers was developed. Reaction of the alcohol and tBDPSCl in DMF with AgNO3, NH4NO3, or NH4ClO4 provides good yields of the corresponding silyl ethers

  开发了一种快速有效的方法来保护伯醇和仲醇的叔丁基二苯基甲硅烷基（tBDPS）醚。醇和tBDPSCl在DMF中与AgNO 3，NH 4 NO 3或NH 4 ClO 4的反应可提供相应甲硅烷基醚的良好收率
• Nonionic Superbase-Catalyzed Silylation of Alcohols
  作者：Bosco A. D'Sa、Dale McLeod、John G. Verkade

  DOI：10.1021/jo9701492

  日期：1997.7.1

  Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)(3)N, Ib, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 degrees C and on rare occasions in DMF from 24 to 80 degrees C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of Ib as a catalyst, tertiary alcohols were recovered unchanged.
• The triisopropylsilyl group as a hydroxyl-protecting function
  作者：Robert F. Cunico、Lewis Bedell

  DOI：10.1021/jo01311a058

  日期：1980.11
• Conformational Analysis of Cyclohexyl Silyl Ethers
  作者：Ernest L. Eliel、Hikmet Satici

  DOI：10.1021/jo00082a036

  日期：1994.2
• CUNICO R. F.; BEDELL L., J. ORG. CHEM., 1980, 45, NO 23, 4797-4798
  作者：CUNICO R. F.、 BEDELL L.

  DOI：——

  日期：——