4-((tert-butyldimethylsilyl)oxy)butyl benzoate | 321887-73-4

• 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-butyldimethylsilyl)oxy)butyl benzoate
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxybutyl benzoate
• CAS: 321887-73-4
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: SVNJZWFDQCXNLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  356.5±25.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((tert-butyldimethylsilyl)oxy)butyl benzoate 在 氯化锆(IV) 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到4-benzoyloxybutan-1-ol
  参考文献：
  名称：

  简便的氯化锆（IV）催化叔丁基二甲基甲硅烷基（TBDMS）醚的选择性脱保护

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(03)01088-8
• 作为产物：
  描述：

  4-benzoyloxybutan-1-ol 、 tert-butyldimethyl(2-methylallyl)silane 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 various solvent(s) 为溶剂， 反应 0.25h， 以95%的产率得到4-((tert-butyldimethylsilyl)oxy)butyl benzoate
  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

• 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。
• 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。
• Ligand-Assisted Rate Acceleration in Lanthanum(III) Isopropoxide Catalyzed Transesterification of Carboxylic Esters
  作者：Manabu Hatano、Yoshiro Furuya、Takumi Shimmura、Katsuhiko Moriyama、Sho Kamiya、Toshikatsu Maki、Kazuaki Ishihara

  DOI：10.1021/ol102753n

  日期：2011.2.4

  The transesterification of an equimolar mixture of carboxylic esters and primary (1 degrees), secondary (2 degrees), and tertiary (3 degrees) alcohols in hydrocarbon solvents was promoted with high efficiency by a lanthanum(III) complex, which was prepared in situ from lanthanum(III) isopropoxide (1 mol %) and 2-(2-methoxyethoxy)ethanol(2 mol %). The present La(III) catalyst was highly effective for the chemoselective transesterification in the presence of competitive 1 degrees- and 2 degrees-amines. Remarkably, esters were obtained in good to excellent yields as colorless materials without an inconvenient workup procedure.
• 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。
• A novel and efficient method for the silylation of alcohols with methallylsilanes catalyzed by Sc(OTf)3
  作者：Takeshi Suzuki、Tsutomu Watahiki、Takeshi Oriyama

  DOI：10.1016/s0040-4039(00)01545-8

  日期：2000.11

  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.