2-Phenoxyethanol, tert-butyldimethylsilyl ether | 143038-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Phenoxyethanol, tert-butyldimethylsilyl ether
• 英文别名: tert-butyl-dimethyl-(2-phenoxyethoxy)silane
• CAS: 143038-69-1
• 化学式: C₁₄H₂₄O₂Si
• 分子量: 252.429
• InChiKey: HTUFPQFETCMQMB-UHFFFAOYSA-N

物化性质

• 沸点：
  289.3±23.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-Phenoxyethanol, tert-butyldimethylsilyl ether 在 P(Me₂CHNCH₂CH₂)3N 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 以95%的产率得到己二酸,聚合2,2-二甲基-1,3-丙二醇和2,5-呋喃二酮,苯酸酯
  参考文献：
  名称：

  P（MeNCH2CH2）3N：叔丁基二甲基甲硅烷基醚脱甲硅基的有效催化剂

  摘要：

  伯醇，仲醇和叔醇的叔丁基二甲基甲硅烷基（TBDMS）醚和酚类TBDMS醚分别在DMSO中，80摄氏度，0.2-0.2％的存在下被甲硅烷基化为相应的醇和酚。 0.4当量的P（MeNCH2CH2）3N。使用P（i-PrNCH2-CH2）3N作为催化剂，从1-辛醇，2-苯氧基乙醇和外消旋α-苯基乙醇的TBDMS醚中获得85-97％的去甲硅烷基化醇产率。这些是非离子碱催化的甲硅烷基醚的脱甲硅烷基化的第一个例子。在与用于TBDMS醚相同的条件下，两种催化剂对叔丁基二苯基甲硅烷基（TBDPS）醚的甲硅烷基化的效率都低得多（产率22-45％）。

  DOI：

  10.1021/jo991591i
• 作为产物：
  描述：

  己二酸,聚合2,2-二甲基-1,3-丙二醇和2,5-呋喃二酮,苯酸酯 、 叔丁基二甲基氯硅烷 在 P(MeNCH₂CH₂)3N 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.3h， 以99%的产率得到2-Phenoxyethanol, tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Nonionic Superbase-Catalyzed Silylation of Alcohols

  摘要：

  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.

  DOI：

  10.1021/jo9701492

文献信息

• One-step conversion of silyl/THP ethers into the corresponding acetates
  作者：Kusum L Chandra、P Saravanan、Vinod K Singh

  DOI：10.1016/s0040-4039(01)00967-4

  日期：2001.7

  A variety of silyl and THP ethers were directly converted into the corresponding acetates using acetic anhydride in the presence of a catalytic amount of Cu(OTf)(2) in CH2Cl2. It was observed that MEM ethers could also be cleaved under the same conditions. The reaction was also studied with other Lewis acids. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Harnessing open-source technology for low-cost automation in synthesis: Flow chemical deprotection of silyl ethers using a homemade autosampling system
  作者：Matthew O'Brien、Lisette Konings、Matthew Martin、Jordan Heap

  DOI：10.1016/j.tetlet.2017.05.008

  日期：2017.6

  An inexpensive homemade 3-axis autosampler was used to facilitate the automation of an acid catalysed flow chemical desilylation reaction. Harnessing open-source software technologies (Python, OpenCV), an automated computer-vision controlled liquid-liquid extraction step was used to provide effective inline purification. A Raspberry Pi single-board computer was employed to interface with the motors used in the autosampler and actuated fluidic valves. (C) 2017 Elsevier Ltd. All rights reserved.
• 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.
• P(MeNCH₂CH₂)₃N:  An Efficient Catalyst for the Desilylation of <i>tert</i>-Butyldimethylsilyl Ethers
  作者：Zhengkun Yu、John G. Verkade

  DOI：10.1021/jo991591i

  日期：2000.4.1

  in 68-94% yield in the presence of 0.2-0.4 equiv of P(MeNCH2CH2)3N. Using P(i-PrNCH2-CH2)3N as the catalyst, 85-97% yields of desilylated alcohols were obtained from TBDMS ethers of 1-octanol, 2-phenoxyethanol, and racemic alpha-phenyl ethanol. These are the first examples of desilylations of silyl ethers catalyzed by nonionic bases. Both catalysts were much less effective for the desilylation of t

  伯醇，仲醇和叔醇的叔丁基二甲基甲硅烷基（TBDMS）醚和酚类TBDMS醚分别在DMSO中，80摄氏度，0.2-0.2％的存在下被甲硅烷基化为相应的醇和酚。 0.4当量的P（MeNCH2CH2）3N。使用P（i-PrNCH2-CH2）3N作为催化剂，从1-辛醇，2-苯氧基乙醇和外消旋α-苯基乙醇的TBDMS醚中获得85-97％的去甲硅烷基化醇产率。这些是非离子碱催化的甲硅烷基醚的脱甲硅烷基化的第一个例子。在与用于TBDMS醚相同的条件下，两种催化剂对叔丁基二苯基甲硅烷基（TBDPS）醚的甲硅烷基化的效率都低得多（产率22-45％）。