[4-(苄氧基)丁氧基](叔丁基)二甲基硅烷 | 105966-46-9

• 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: [4-(苄氧基)丁氧基](叔丁基)二甲基硅烷
• 英文名称: [4-(benzyloxy)butoxy](tert-butyl)dimethylsilane
• 英文别名: Tert-butyl-dimethyl-(4-phenylmethoxybutoxy)silane
• CAS: 105966-46-9
• 化学式: C₁₇H₃₀O₂Si
• 分子量: 294.51
• InChiKey: KOCHSHVSERYHJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.1±25.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  [4-(苄氧基)丁氧基](叔丁基)二甲基硅烷 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 1,4-丁二醇
  参考文献：
  名称：

  Selective acceleration for deprotection of benzyl ethers with Ti-HMS

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)02145-5
• 作为产物：
  描述：

  4-苄氧基-1-丁醇 、 tert-butyldimethyl(2-methylallyl)silane 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 various solvent(s) 为溶剂， 反应 0.25h， 以92%的产率得到[4-(苄氧基)丁氧基](叔丁基)二甲基硅烷
  参考文献：
  名称：

  A novel and efficient method for the silylation of alcohols with methallylsilanes catalyzed by Sc(OTf)3

  摘要：

  Reaction of alcohols with methallylsilanes in the presence of a catalytic amount of Sc(OTf)(3) provides efficiently the corresponding alkyl silyl ethers. By using microencapsulated (MC) Sc(OTf)(3), which can be easily recovered and reused, yields of alkyl silyl ethers are improved and the work-up process after completion of the reaction is considerably simplified. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01545-8

文献信息

• Facile and Highly Selective Deprotection of <i>tert</i>‐Butyldimethyl Silyl Ethers using Sulfated SnO₂ as a Solid Catalyst
  作者：Mahesh H. Bhure、Indresh Kumar、Arun D. Natu、Chandrashekhar V. Rode

  DOI：10.1080/00397910701767056

  日期：2008.1.1

  Abstract Highly selective deprotection of tert‐butyldimethylsilyl ethers at room temperature has been described using sulfated SnO2 as an efficient solid catalyst.

  摘要 已经描述了使用硫酸化 SnO2 作为有效固体催化剂在室温下对叔丁基二甲基甲硅烷基醚进行高选择性脱保护。
• A facile zirconium(IV) chloride catalysed selective deprotection of t-butyldimethylsilyl (TBDMS) ethers
  作者：G.V.M. Sharma、B. Srinivas、Palakodety Radha Krishna

  DOI：10.1016/s0040-4039(03)01088-8

  日期：2003.6

  A simple and efficient protocol for the selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using 20 mol% ZrCl4 in 20–45 min and in high yields, is reported, wherein it is demonstrated that acid and base sensitive groups and allylic and benzylic groups are unaffected.

  报告了一种简单有效的方案，可在20-45分钟内以高收率使用20 mol％ZrCl 4选择性脱保护叔丁基二甲基甲硅烷基（TBDMS）醚，其中证明了对酸和碱敏感的基团，烯丙基和苄基团体不受影响。
• DIRECT CONVERSION OF SILYL ETHERS OR TETRAHYDROPYRANYL ETHERS INTO THE CORRESPONDING DIPHENYLMETHYL ETHERS
  作者：Takeshi Suzuki、Kumiko Kobayashi、Kojiro Noda、Takeshi Oriyama

  DOI：10.1081/scc-100105322

  日期：2001.1

  Direct conversion of alcohol silyl ethers into the corresponding diphenylmethyl (DPM) ethers can be easily performed by the reaction with diphenylmethyl formate in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate. By the additional use of triethylsilane, tetrahydropyranyl ethers can be also converted into the corresponding DPM ethers.

  在催化量的三氟甲磺酸三甲基甲硅烷基酯存在下，通过与甲酸二苯甲酯反应，可以很容易地将醇甲硅烷基醚直接转化为相应的二苯甲基 (DPM) 醚。通过额外使用三乙基硅烷，四氢吡喃基醚也可以转化为相应的 DPM 醚。
• Silylated Cyclohexadienes in Radical Chain Hydrosilylations
  作者：Stephan Amrein、Armido Studer

  DOI：10.1002/1522-2675(200210)85:10<3559::aid-hlca3559>3.0.co;2-6

  日期：2002.10

  A new method for the mild radical hydrosilylation of alkenes and alkynes is described. Silylated cyclohexadienes that can be readily prepared on large scale are used as radical hydrosilylating reagents. Non-activated alkenes and alkynes are hydrosilylated in high yields. The reaction can be combined with CC bond formation, as demonstrated for the preparation of silylated cycloalkanes from the corresponding

  描述了烯烃和炔烃的温和自由基氢化硅烷化的新方法。可以容易地大规模制备的甲硅烷基化环己二烯被用作自由基氢化硅烷化试剂。非活化烯烃和炔烃以高产率氢化硅烷化。该反应可以与 CC 键的形成相结合，如从相应的二烯制备甲硅烷基化环烷烃所证明的那样。此外，自由基氢化硅烷化与β-断裂反应相结合用于合成烯丙基硅烷和醛和酮的氢化硅烷化提供受保护的醇可以很容易地通过该策略进行。
• A Novel and Chemoselective Transformation of Alcohol Silyl Ethers into the Corresponding Tetrahydropyranyl Ethers
  作者：Takeshi Suzuki、Takeshi Oriyama

  DOI：10.1055/s-2001-12343

  日期：——

  Direct conversion of alcohol silyl ethers into the corresponding tetrahydropyranyl (THP) ethers can be easily performed by reaction with THP acetate under the influence of a catalytic amount of tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf). Aliphatic TBS ether can be selectively transformed into the corresponding THP ether in the presence of phenolic TBS ether.

  在一定量的三氟甲磺酸叔丁基二甲基硅烷（TBSOTf）催化剂的作用下，通过与乙酸四氢吡喃酯（THP）反应，可以很容易地将醇硅醚直接转化为相应的四氢吡喃（THP）醚。脂肪族 TBS 醚可在酚类 TBS 醚的存在下选择性地转化为相应的 THP 醚。