3-(t-Butyl-dimethylsilyloxy)-1-butanol | 68726-87-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-(t-Butyl-dimethylsilyloxy)-1-butanol
• 英文别名: 3-(tert-butyldimethylsiloxy)butanol；(+/-)-3-(t-butyldimethylsilyloxy)butan-1-ol；(3RS)-3-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol；3-(tert-butyldimethylsiloxy)-1-butanol；1-Butanol, 3-t-butyldimethylsilyloxy-；3-[tert-butyl(dimethyl)silyl]oxybutan-1-ol
• CAS: 68726-87-4
• 化学式: C₁₀H₂₄O₂Si
• 分子量: 204.385
• InChiKey: PIWCWAVOQLFTBN-UHFFFAOYSA-N

物化性质

• 沸点：
  232.2±23.0 °C(predicted)
• 密度：
  0.874±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(t-Butyl-dimethylsilyloxy)-1-butanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4-iodobutan-2-yloxy)-(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Intramolecular Oxyallyl–Carbonyl (3 + 2) Cycloadditions

  摘要：

  Cycloadditions involving oxyallyl intermediates typically require an electron-rich diene or alkene, but we have discovered the first examples of the cycloaddition of heteroatom-stabilized oxyallyls onto carbonyl groups. An oxazolidinone-substituted oxyallyl undergoes chemoselective (3 + 2) cycloaddition onto the carbonyl group of a tethered dienone in preference to formation of the expected (4 + 3) cycloadduct. Density functional theory calculations indicated that the (3 + 2) cycloaddition takes place through a concerted, highly asynchronous mechanism. The transition state features simultaneous interactions of the oxyallyl LUMO with the carbonyl pi and lone-pair orbitals, making this reaction "hemipseudopericyclic" (halfway between purely pericyclic and purely pseudopericyclic). Further (3 + 2) cycloadditions involving tethered phenyl ketones and a tethered enone were predicted theoretically and verified experimentally.

  DOI：

  10.1021/ja312459b
• 作为产物：
  描述：

  ethyl 3-(tert-butyldimethylsilyloxy)butanoate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3-(t-Butyl-dimethylsilyloxy)-1-butanol
  参考文献：
  名称：

  多烯大环内酯匹马星的聚合合成策略

  摘要：

  描述了由3-羟基戊二酸二甲酯合成代表多烯大环内酯比马星霉素的Cl-11和C12-25的两个手性片段。

  DOI：

  10.1016/s0040-4039(00)88094-6

文献信息

• Selective Protection of Secondary Alcohols by Using Formic Acid as a Mild and Efficient Deprotection Reagent for Primary tert-Butyldimethylsilyl Ethers
  作者：Krishna Sapkota、Faqing Huang

  DOI：10.1055/s-0037-1611757

  日期：2019.10

  A mild, efficient, and environmentally friendly method for the selective protection of secondary hydroxyl groups is described. The method involves the protection of both primary and secondary hydroxyl groups as tert-butyldimethylsilyl (TBDMS) ethers and selective deprotection of the primary TBDMS group with formic acid in acetonitrile/water. The rates of desilylation of primary and secondary TBDMS

  描述了一种用于选择性保护仲羟基的温和、高效且环保的方法。该方法包括将伯羟基和仲羟基保护为叔丁基二甲基甲硅烷基 (TBDMS) 醚，并在乙腈/水中用甲酸对伯 TBDMS 基团进行选择性脱保护。测定了不同浓度甲酸对初级和次级 TBDMS 醚的脱甲硅烷基化速率。发现浓度为 5-20% 的甲酸可以选择性地对初级 TBDMS 醚进行脱保护，同时保持 95% 以上的二级对应物完好无损。
• Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin
  作者：Lutz F. Tietze、Kersten M. Gericke、Ramakrishna Reddy Singidi、Ingrid Schuberth

  DOI：10.1039/b700838d

  日期：——

  Two high-yielding strategies for the synthesis of 4H-anthra[1,2-b]pyran antibiotics have been developed giving access to novel antitumor agent (ED(50) 1.5 microm) and to (S)-espicufolin (3). A key step for the assembly of the tetracyclic 4H-anthra[1,2-b]pyran-4,7,12-trione skeleton is the nucleophilic addition of an aryl lithium species onto an aldehyde which allows the introduction of either an ynone

  已经开发了两种合成4H-蒽[1,2-b]吡喃抗生素的高产策略，可以使用新型抗肿瘤药（ED（50）1.5 microm）和（S）-espicufolin（3）。组装四环4H-蒽[1,2-b]吡喃-4,7,12-三酮骨架的关键步骤是芳基锂物质在醛上的亲核加成，从而允许引入炔酮或1,3-二酮侧链，用作酸催化环化反应的前体。
• Doppelt und dreifach funktionalisierte, enantiomerenreine C₄-Synthesebausteine aus β-Hydroxybuttersäure, Äpfelsäure und Weinsäure
  作者：Ernst Hungerbühler、Dieter Seebach、Daniel Wasmuth

  DOI：10.1002/hlca.19810640523

  日期：1981.7.22

  Enantiomerically Pure Synthetic Building Blocks with Four C-Atoms and Two or Three Functional Groups from β-Hydroxy-butanoic, Malic, and Tartaric Acid

  具有四个C原子和两个或三个来自β-羟基丁酸，苹果酸和酒石酸的官能团的对映体纯合成构件
• 1,8-Diazabicyclo[5.4.0]undec-7-ene. An Effective and Selective Catalyst for the<i>t</i>-Butyldimethylsilylation of Alcohols
  作者：Sunggak Kim、Heung Chang

  DOI：10.1246/bcsj.58.3669

  日期：1985.12

  The use of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst has been found to be very effective and selective in the t-butyldimethylsilylation of primary and secondary alcohols.

  使用1,8-二氮杂双环[5.4.0]十一烯（DBU）作为催化剂在初级和次级醇的t-丁基二甲基硅烷化反应中被发现非常有效且选择性强。
• A Mild and Efficient Desilylation of <i>O</i>-<i>tert</i>-Butyldimethylsilyl Ethers Mediated by Chlorotrimethylsilane and Potassium Fluoride Dihydrate in Acetonitrile
  作者：Wei-Dong Li、Yu Peng

  DOI：10.1055/s-2006-932474

  日期：——

  Desilylation of O-tert-butyldimethylsilyl ethers was achieved by a reagent system consisting of chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile. This alternative desilylation procedure is chemoselective, generally effective and operationally simple, and should find practical applications in organic synthesis.

  O-叔丁基二甲基甲硅烷基醚的脱甲硅烷基化是通过由氯三甲基硅烷和二水合氟化钾在乙腈中组成的试剂系统实现的。这种替代的脱甲硅烷化过程具有化学选择性，通常有效且操作简单，应该在有机合成中找到实际应用。