2-[4'-(triethylsilyloxy)phenyl]ethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[4'-(triethylsilyloxy)phenyl]ethanol
• 英文别名: 2-(4-Triethylsilyloxyphenyl)ethanol；2-(4-triethylsilyloxyphenyl)ethanol
• 化学式: C₁₄H₂₄O₂Si
• 分子量: 252.429
• InChiKey: MDWZAFAFLQTYHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对羟基苯乙醇 在 咪唑 、 1-氯乙基氯甲酸酯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.02h， 生成 2-[4'-(triethylsilyloxy)phenyl]ethanol
  参考文献：
  名称：

  Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol

  摘要：

  Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.043

文献信息

• Recombinant silicateins as model biocatalysts in organosiloxane chemistry
  作者：S. Yasin Tabatabaei Dakhili、Stephanie A. Caslin、Abayomi S. Faponle、Peter Quayle、Sam P. de Visser、Lu Shin Wong

  DOI：10.1073/pnas.1613320114

  日期：2017.7.3

  with a range of model organosilanols and silyl ethers. The enzymes’ kinetic parameters were obtained by a high-throughput colorimetric assay based on the hydrolysis of 4-nitrophenyl silyl ethers. These assays showed unambiguous catalysis with kcat/Km values on the order of 2–50 min−1 μM−1. Condensation reactions were also demonstrated by the generation of silyl ethers from their corresponding silanols

  天然海绵中的硅酸盐酶家族（门孔植物）在催化无机二氧化硅结构的形成方面具有独特的性质，该有机二氧化硅可被有机体整合到其骨架中。但是，到目前为止，仍未充分探索由这些酶催化的有机硅氧烷的合成。为了研究这些酶与这一重要类化合物的反应性，使用一系列模型有机硅烷醇和甲硅烷基醚研究了它们对Si–O键水解和缩合的催化作用。通过基于4-硝基苯基甲硅烷基醚的水解的高通量比色测定法获得了酶的动力学参数。这些测定显示出明确的催化作用，k cat / K m值约为2–50分钟-1 μM -1。缩合反应还通过由其相应的硅烷醇和醇生成甲硅烷基醚来证明。值得注意的是，当与同时带有脂肪族和芳香族羟基的底物一起出现时，与非酶甲硅烷基化形成鲜明对比的是，该酶优先使后者基团甲硅烷基化。此外，硅酸酯类能够催化转醚化，其中来自一种甲硅烷基醚的甲硅烷基可以转移到受体醇上。尽管与蛋白酶组织蛋白酶L具有紧密的序列同源性，但是当针对相似的底
• Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
  作者：Chang-Eun Yeom、Young Jong Kim、So Young Lee、Yong Je Shin、B. Moon Kim

  DOI：10.1016/j.tet.2005.10.043

  日期：2005.12

  Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time. (c) 2005 Elsevier Ltd. All rights reserved.