(2-(苄氧基)乙氧基)(叔丁基)二甲基硅烷 | 104948-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-(苄氧基)乙氧基)(叔丁基)二甲基硅烷
• 英文名称: (2-Benzyloxy-ethoxy)-tert-butyl-dimethyl-silane
• 英文别名: Tert-butyl-dimethyl-(2-phenylmethoxyethoxy)silane
• CAS: 104948-22-3
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: HICHPDOSCBNTQY-UHFFFAOYSA-N

物化性质

• 沸点：
  288.4±15.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-(苄氧基)乙氧基)(叔丁基)二甲基硅烷 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到乙二醇
  参考文献：
  名称：

  The undesirable lability of tert-butyldimethylsilyl ethers under Pd/C-catalyzed hydrogenation conditions and solution of the problem by using a Pd/C(en) catalyst

  摘要：

  While the frequent and unexpected loss of the TBDMS protective group of a variety of hydroxylic functions was demonstrated under neutral and mild hydrogenation conditions using 10% Pd/C, the undesirable problem was perfectly overcome by using a 10% Pd/C-ethylenediamine complex catalyst. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00935-7

文献信息

• Undesirable deprotection of O-TBDMS groups by Pd/C-catalyzed hydrogenation and chemoselective hydrogenation using a Pd/C(en) catalyst
  作者：Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4020(01)00060-6

  日期：2001.3

  In general, O-TBDMS protective groups have been believed to be stable toward Pd/C-catalyzed hydrogenation conditions. In practice, however, frequent and unexpected loss of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. When a 10% Pd/C-ethylenediamine complex catalyst [10% Pd/C(en)] was used instead of 10% Pd/C, the undesirable problem was perfectly overcome and the chemoselective hydrogenation of reducible functionalities leaving intact the TBDMS protective group was achieved. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Selective acceleration for deprotection of benzyl ethers with Ti-HMS
  作者：Akichika Itoh、Tomohiro Kodama、Shiro Maeda、Yukio Masaki

  DOI：10.1016/s0040-4039(98)02145-5

  日期：1998.12

  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.
• Calcium in liquid ammonia for the reduction of benzyl ethers. Mechanistic clues derived from chemoselectivity studies
  作者：Jih Ru Hwu、Vincent Chua、Jean E. Schroeder、Richard E. Barrans、Kevin P. Khoudary、Naelong Wang、John M. Wetzel

  DOI：10.1021/jo00374a048

  日期：1986.11
• The undesirable lability of tert-butyldimethylsilyl ethers under Pd/C-catalyzed hydrogenation conditions and solution of the problem by using a Pd/C(en) catalyst
  作者：Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4039(00)00935-7

  日期：2000.7

  While the frequent and unexpected loss of the TBDMS protective group of a variety of hydroxylic functions was demonstrated under neutral and mild hydrogenation conditions using 10% Pd/C, the undesirable problem was perfectly overcome by using a 10% Pd/C-ethylenediamine complex catalyst. (C) 2000 Elsevier Science Ltd. All rights reserved.