4-tert-butyl-butyldimethylsilyloxybenzyl alcohol THP ether | 249284-23-9

• 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: 4-tert-butyl-butyldimethylsilyloxybenzyl alcohol THP ether
• 英文别名: Tert-butyl-dimethyl-[4-(oxan-2-yloxymethyl)phenoxy]silane
• CAS: 249284-23-9
• 化学式: C₁₈H₃₀O₃Si
• 分子量: 322.52
• InChiKey: BBPGBGBIIWBADW-UHFFFAOYSA-N

物化性质

• 沸点：
  369.3±42.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-butyldimethylsilyloxybenzyl alcohol THP ether 在 碘 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到对羟基苯甲醇
  参考文献：
  名称：

  Kumar, H. M. Sampath; Reddy, B. V. Subba; Reddy, E. Jagan, Chemistry Letters, 1999, # 9, p. 857 - 858

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 4-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]-苯甲醇 在 calcium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以94%的产率得到4-tert-butyl-butyldimethylsilyloxybenzyl alcohol THP ether
  参考文献：
  名称：

  在中性和中性条件下使用无水氯化钙使醇和苯酚容易地进行四氢吡喃基化反应

  摘要：

  在二氯甲烷中，在催化量的无水氯化钙存在下，用各种醇和酚 处理3,4-二氢-2 H- 吡喃，几乎在中性条件下提供了四氢吡喃基醚。

  DOI：

  10.1007/s00706-002-0468-9

文献信息

• Generally Applicable Organocatalytic Tetrahydropyranylation of Hydroxy Functionalities with Very Low Catalyst Loading
  作者：Peter Schreiner、Mike Kotke

  DOI：10.1055/s-2007-965917

  日期：2007.3

  This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state.

  本文介绍了首个无酸、有机催化的四氢吡喃和2-甲氧基丙烯对醇、酚及其他ROH衍生物的保护方法，利用了特权的N,N'-双[3,5-双(三氟甲基)苯基]硫脲及其聚苯乙烯结合类似物。这些反应广泛适用于（包括制备规模）对酸敏感的底物，如醛醇产物、羟基酯、缩醛、硅烷保护的醇和氰醇。催化效率非常高，转化数达到10万，转化频率高达每小时5700次，催化剂负载量低至0.001 mol%。通过计算支持的机理解释强调了氢键辅助的醇异裂和过渡态中氧阴离子穴的优先稳定。
• Indium triiodide catalysed one-step conversion of tetrahydropyranyl ethers to acetates with high selectivity
  作者：Brindaban C. Ranu、Alakananda Hajra

  DOI：10.1039/b100014b

  日期：——

  A very simple and efficient method has been developed for the chemoselective one-step conversion of tetrahydropyranyl ethers of primary alcohols to the corresponding acetates through an indium triiodide catalysed transesterification process in ethyl acetate.

  一种非常简单高效的方法被开发出来，可以通过在乙酸乙酯中以碘化铟为催化剂的转酯化过程，将初级醇的四氢吡喃醚选择性地一步转化为相应的醋酸酯。
• Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate
  作者：Brindaban C. Ranu、Alakananda Hajra

  DOI：10.1039/b104055n

  日期：——

  A simple and efficient method is developed for the chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates by indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process.

  我们开发了一种简单而高效的方法，通过铟三碘催化去保护和随后的醋酸乙酯转酯化过程，将初级醇的四氢吡喃基（THP）和甲氧基甲基（MOM）醚选择性地一锅转化为相应的醋酸酯。
• A Mild, Efficient and Selective Cleavage of Aryl<i>tert</i>-Butyldimethysilyl Ethers Using KOH in Ethanol
  作者：Zhi-Yong Jiang、Yan-Guang Wang

  DOI：10.1246/cl.2003.568

  日期：2003.7

  An efficient and selective method for the deprotection of aryl tert-butyldimethysilyl (TBS) ethers is described. The protecting group TBS could be cleaved from aryl silyl ethers in the prensence of alkyl TBS ethers using KOH in ethanol at room temperature to give the corresponding phenols in excellent yields (87–99%).

  描述了一种高效且选择性的去保护芳基叔丁基二甲基硅烷（TBS）醚的方法。在乙醇中使用KOH在室温下，在烷基TBS醚存在的条件下，可以从芳基硅醚中去除保护基TBS，得到相应的酚类化合物，产率极高（87%–99%）。
• A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers
  作者：Abu T. Khan、Samimul Islam、Lokman H. Choudhury、Subrata Ghosh

  DOI：10.1016/j.tetlet.2004.11.011

  日期：2004.12

  Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemo selectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions. (C) 2004 Published by Elsevier Ltd.