Silane, (1,1-dimethylethyl)dimethyl[[5-(phenylmethoxy)pentyl]oxy]- | 220061-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Silane, (1,1-dimethylethyl)dimethyl[[5-(phenylmethoxy)pentyl]oxy]-
• 英文别名: tert-butyl-dimethyl-(5-phenylmethoxypentoxy)silane
• CAS: 220061-39-2
• 化学式: C₁₈H₃₂O₂Si
• 分子量: 308.536
• InChiKey: FFCMMRSCEIBHAF-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±25.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Silane, (1,1-dimethylethyl)dimethyl[[5-(phenylmethoxy)pentyl]oxy]- 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到1,5-戊二醇
  参考文献：
  名称：

  Selective acceleration for deprotection of benzyl ethers with Ti-HMS

  摘要：

  Ti-HMS, a TI-loaded hexagonal mesoporous silica, was found to accelerate deprotection of benzyl ethers under hydrogenolytic conditions with palladium catalyst. Such acid-sensitive functional groups as silyl ether and acetal moieties in the molecule were little affected by Ti-HMS, which possesses Lewis acid sites due to Ti-atom. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02145-5
• 作为产物：
  描述：

  溴甲苯 、 Silane, [1,5-pentanediylbis(oxy)]bis[(1,1-dimethylethyl)dimethyl- 生成 Silane, (1,1-dimethylethyl)dimethyl[[5-(phenylmethoxy)pentyl]oxy]-
  参考文献：
  名称：

  NICOLAOU, K. C.;HWANG, C. -K.;MARRON, B. E.;DEFREES, S. A.;COULADOUROS, E+, J. AMER. CHEM. SOC., 112,(1990) N, C. 3040-3054

  摘要：

  DOI：

文献信息

• A Simple and Useful Synthetic Protocol for Selective Deprotection oftert-Butyldimethylsilyl (TBS) Ethers
  作者：Abu T. Khan、Subrata Ghosh、Lokman H. Choudhury

  DOI：10.1002/ejoc.200400031

  日期：2004.5

  A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds

  在室温下，在 5 mol% 的丙酮基三苯基溴化鏻 (ATPB) 存在下，多种叔丁基二甲基甲硅烷基醚 1 可以很容易地裂解为相应的母体羟基化合物 2。此外，叔丁基二苯基甲硅烷基醚也可以通过使用 20 mol% 的相同催化剂进行裂解。在芳基叔丁基二甲基甲硅烷基醚存在下，烷基叔丁基二甲基甲硅烷基醚可以化学选择性地脱保护为羟基化合物。一些主要优点是反应条件温和、无需水处理、高效和化学选择性以及与其他保护基团的相容性；在这些实验条件下，芳环中没有发生溴化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• A Highly Efficient and UsefulSynthetic Protocol for the Cleavage of<i>tert</i>-Butyldimethylsilyl(TBS) Ethers Using a Catalytic Amount of Acetyl Chloridein Dry Methanol
  作者：Abu T. Khan、Ejabul Mondal

  DOI：10.1055/s-2003-38360

  日期：——

  A wide variety of tert-butyldimethylsilyl (TBS) ethers as well as tert-butyldiphenylsilyl (TBDPS) ethers 1 can be easily deprotected to the corresponding parent hydroxyl compounds 2 by employing catalytic amounts of acetyl chloride in dry MeOH at 0 °C to room temperature in good yields. Some of the major advantages are mild conditions, high efficiency, high selectivity, high yields, easy operation, and also compatibility with other protecting groups. Furthermore, no acetylation nor chlorination takes place under the experimental conditions.

  各种叔丁基二甲基硅醚和叔丁基二苯基硅醚（简称TBS和TBDPS醚）可以利用催化量的乙酰氯在干燥甲醇中，从0°C至室温条件下，以良好的产率轻松脱保护为相应的母体羟基化合物。这种方法的主要优点包括条件温和、高效、高选择性、高产率、操作简便，并且与其他保护基团兼容。此外，在实验条件下不会发生乙酸化或氯化反应。
• Deprotection of t-butyldimethylsilyl ethers promoted by cerium(IV) triflate
  作者：Giuseppe Bartoli、Giovanna Cupone、Renato Dalpozzo、Antonio De Nino、Loredana Maiuolo、Antonio Procopio、Letizia Sambri、Antonio Tagarelli

  DOI：10.1016/s0040-4039(02)01254-6

  日期：2002.8

  t-Butyldimetylsilyl ethers are mildly cleft by catalytic amounts of cerium(IV) triflate. Dependence from water amount was observed.

  催化量的三氟甲磺酸铈（IV）轻度裂化了叔丁基二甲基甲硅烷基醚。观察到对水量的依赖性。
• Tetrabutylammonium Tribromide (TBATB)−MeOH:  An Efficient Chemoselective Reagent for the Cleavage of <i>tert</i>-Butyldimethylsilyl (TBDMS) Ethers
  作者：Rangam Gopinath、Bhisma K. Patel

  DOI：10.1021/ol006720s

  日期：2000.12.1

  [GRAPHICS]TBDMS, THP, and DMT ethers are efficiently deprotected with tetrabutylammonium tribromide in methanol, The apparent order of stability of different protecting group is phenolic TBDMS > 1 degrees OTBDPS > 2 degrees OTBDMS > 2 degrees OTHP > 1 degrees OTHP > 1 degrees OTBDMS > 1 degrees ODMT. TBDMS ether has been cleaved selectively in the presence of isopropylidine, an, Ac, Bz, THP, and TBDPS groups. This method is high yielding, fast, clean, safe, cost effective, and therefore most suitable for practical organic synthesis.
• A facile and catalytic method for selective deprotection of tert-butyldimethylsilyl ethers with copper(II) bromide
  作者：Suchitra Bhatt、Sandip K. Nayak

  DOI：10.1016/j.tetlet.2006.09.073

  日期：2006.11

  Copper(H) bromide is found to be a simple and efficient catalyst for selective deprotection of tert-butyidimethylsilyl ethers of alcohols/phenols at ambient temperature. Various labile functional groups such as ketal, alkene, ketone, OTBDPS, OTHP and allyl and benzyl ethers are found to be compatible under the reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.