decyl β-(trimethylsilyl)ethoxymethyl ether

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: decyl β-(trimethylsilyl)ethoxymethyl ether
• 英文别名: 2-(Decoxymethoxy)ethyl-trimethylsilane
• 化学式: C₁₆H₃₆O₂Si
• 分子量: 288.546
• InChiKey: INIMDYVDYYPQRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  decyl β-(trimethylsilyl)ethoxymethyl ether 在 magnesium bromide 作用下， 以 乙醚 、 硝基甲烷 为溶剂， 反应 5.0h， 以99%的产率得到癸醇
  参考文献：
  名称：

  新型SEM醚脱保护剂：使用溴化镁的非常温和且选择性的方法

  摘要：

  通过MgBr（2）/ Et（2）O / MeNO（2）脱保护方案，已为包含SEM醚基的多功能底物建立了新的不稳定性和稳定性序列。

  DOI：

  10.1021/ol0057784
• 作为产物：
  描述：

  (((癸氧基)甲氧基)甲基)苯 在 4-二甲氨基吡啶 、 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 decyl β-(trimethylsilyl)ethoxymethyl ether
  参考文献：
  名称：

  The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups

  摘要：

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.048

文献信息

• Novel Deprotection of SEM Ethers:  A Very Mild and Selective Method Using Magnesium Bromide
  作者：Alexandros Vakalopoulos、H. M. R. Hoffmann

  DOI：10.1021/ol0057784

  日期：2000.5.1

  New lability and stability sequences have been established for multifunctional substrates containing SEM ether group(s) by a MgBr(2)/Et(2)O/MeNO(2) deprotection protocol.

  通过MgBr（2）/ Et（2）O / MeNO（2）脱保护方案，已为包含SEM醚基的多功能底物建立了新的不稳定性和稳定性序列。
• An Efficient and Highly Selective Deprotecting Method for β-(Trimethylsilyl)ethoxymethyl Ethers
  作者：Ming-Yi Chen、Adam Shih-Yuan Lee

  DOI：10.1021/jo0107204

  日期：2002.2.1

  A series of beta-(trimethylsilyl)ethoxymethyl ethers were hydrolyzed to their corresponding alcohols in high yields by using a catalytic amount of CBr4 (15%) in MeOH under refluxing reaction conditions. The chemoselective deprotection between trialkylsilyl and beta-(trimethylsilyl)ethoxymethyl-protected alcohols can be achieved by using an alcohol with steric hindrance such as iPrOH. The selectivity also can be achieved in the CBr4/MeOH reaction mixture under ultrasonic reaction conditions.o
• The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups
  作者：Hiromichi Fujioka、Yutaka Minamitsuji、Ozora Kubo、Kento Senami、Tomohiro Maegawa

  DOI：10.1016/j.tet.2011.02.048

  日期：2011.4

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.