1-(2'-furyl)-2-trimethylsilanylethan-1-ol | 1578-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-(2'-furyl)-2-trimethylsilanylethan-1-ol
• 英文别名: 1-(2-furyl)-2-trimethylsilanylethan-1-ol；1-(2'-furyl)-2-(trimethylsilyl)-ethanol；1-(2'-furyl)-2-trimethylsilylethan-1-ol；1-(2-furyl)-2-(trimethylsilyl)ethanol；1-furan-2-yl-2-trimethylsilanyl-ethanol；1-Furyl-2-trimethylsilylethanol-1；1-(furan-2-yl)-2-trimethylsilylethanol
• CAS: 1578-26-3
• 化学式: C₉H₁₆O₂Si
• 分子量: 184.31
• InChiKey: RAVFNFXEDAMXDW-UHFFFAOYSA-N

物化性质

• 沸点：
  75-76 °C(Press: 1 Torr)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2'-furyl)-2-trimethylsilanylethan-1-ol 在 4-二甲氨基吡啶 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 碳酸氢钠 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 23.0h， 生成 (2R)-2-tert-butyldimethylsilanyloxymethyl-6-hydroxy-6H-pyran-3-one
  参考文献：
  名称：

  Syntheses of four d- and l-hexoses via diastereoselective and enantioselective dihydroxylation reactions

  摘要：

  An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols call be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-delta-lactones were synthesized in eight steps and similar to 20% overall yield from furfural. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00031-8
• 作为产物：
  描述：

  糠醛 、 氯甲基三甲基硅烷 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以99%的产率得到1-(2'-furyl)-2-trimethylsilanylethan-1-ol
  参考文献：
  名称：

  β-甲硅烷基对手性α-芳基醇在弗瑞德-克拉夫特烷基化中手性记忆的影响

  摘要：

  发现铁盐催化的具有三甲基甲硅烷基的手性α-芳基醇的弗瑞德-克拉夫茨烷基化可继续保留羟基作为离去基团的构型。该系统手性的记忆源于三甲基甲硅烷基对碳阳离子中间体的β-甲硅烷基作用。

  DOI：

  10.1021/acs.orglett.5b01582

文献信息

• Hydrazines and Azides via the Metal-Catalyzed Hydrohydrazination and Hydroazidation of Olefins
  作者：Jérôme Waser、Boris Gaspar、Hisanori Nambu、Erick M. Carreira

  DOI：10.1021/ja062355+

  日期：2006.9.1

  which the H and the N atoms come from two different reagents, a silane and an oxidizing nitrogen source (azodicarboxylate or sulfonyl azide). The hydrohydrazination reaction using di-tert-butyl azodicarboxylate is characterized by its ease of use, large functional group tolerance, and broad scope, including mono-, di-, tri-, and tetrasubstituted olefins. Key to the development of the hydroazidation

  报道了 Co 和 Mn 催化的烯烃加氢肼和加氢叠氮化反应的发现、研究和实施。这些反应等效于 CC 双键与受保护的肼或偶氮酸的直接加氢胺化，但基于不同的概念，其中 H 和 N 原子来自两种不同的试剂，硅烷和氧化性氮源（偶氮二羧酸或磺酰叠氮化物） ）。使用偶氮二羧酸二叔丁酯的加氢肼反应具有使用方便、官能团耐受性大、适用范围广的特点，包括单、二、三和四取代烯烃。氢叠氮化反应发展的关键是使用磺酰叠氮化物作为氮源和叔丁基过氧化氢的活化作用。发现该反应对于单、二和三取代烯烃的官能化是有效的，并且只有少数官能团是不能容忍的。获得的烷基叠氮化物是通用中间体，可以在不分离叠氮化物的情况下转化为游离胺或三唑。初步的机理研究表明，烯烃的氢化钴是限速的，然后是胺化反应。不能排除并可能涉及自由基中间体。然后进行胺化反应。不能排除并可能涉及自由基中间体。然后进行胺化反应。不能排除并可能涉及自由基中间体。
• C2-Alkenylation of N-heteroaromatic compounds via Brønsted acid catalysis
  作者：Giacomo E. M. Crisenza、Elizabeth M. Dauncey、John F. Bower

  DOI：10.1039/c6ob00705h

  日期：——

  simple Brønsted acid catalysed union of diverse heteroarene N-oxides with alkenes. The approach is notable because (a) it is operationally simple, (b) the Brønsted acid catalyst is cheap, non-toxic and sustainable, (c) the N-oxide activator disappears during the reaction, and (d) water is the sole stoichiometric byproduct of the process. The new protocol offers orthogonal functional group tolerance to

  取代的杂芳族化合物，特别是那些基于吡啶的杂芳族化合物，在药物发现和药物化学中占有重要的地位。然而，由于（a）在该位点安装卤素的困难和（b）C 2杂芳基-金属试剂的不稳定性，使6元杂芳烃的C 2位官能化具有挑战性。在这里我们表明，C2-链烯基杂芳族化合物可以通过简单的布朗斯台德酸催化的各种杂芳烃N-氧化物与烯烃的结合而获得。该方法是显着的，因为（a）它在操作上简单，（b）该布朗斯台德酸催化剂是便宜的，无毒的和可持续的，（c）该Ñ-氧化物活化剂在反应过程中消失，并且（d）水是该过程的唯一化学计量副产物。新协议提供了对金属催化方法的正交官能团耐受性，可以轻松整合到合成序列中以提供多官能化靶标。从更广泛的意义上说，这项研究证明了如何仍然可以使用经典的有机反应性为当代合成挑战提供解决方案，而使用过渡金属催化可能会解决这些挑战。
• Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols
  作者：Mika Shiramizu、F. Dean Toste

  DOI：10.1002/anie.201203877

  日期：2012.8.6

  important for the conversion of biomass into chemicals and fuels. The methyltrioxorhenium‐catalyzed deoxydehydration reaction was successfully applied to this purpose using another alcohol as solvent/reductant. The reaction was highly stereospecific, affording linear polyene products from C4–C6 sugar alcohols and aromatic compounds from C4–C6 sugars.

  将糖转变为油：糖部分的脱氧反应对于将生物质转化为化学物质和燃料非常重要。使用另一种醇作为溶剂/还原剂，成功地将甲基三氧合or催化的脱氧脱水反应应用于此目的。该反应是高度立体，得到线性多烯的产品选自C 4 -C 6糖醇和芳族化合物选自C 4 -C 6克的糖。
• Synthesis of <scp>d</scp>- and <scp>l</scp>-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran
  作者：Michael H. Haukaas、George A. O'Doherty

  DOI：10.1021/ol006907j

  日期：2001.2.1

  [figure: see text] The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing beta-hydroxyfurfurylamine 5a with enantioexcess of > 86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The

  [图：见正文] Sharpless催化不对称氨基羟基化反应已应用于2-乙烯基呋喃，生产的β-羟基糠胺5a的对映体过量> 86％，糠醛的收率为21％。Cbz和TBS保护的氨基醇5a以五到七个步骤转化为脱氧甘露糖霉素（DMJ）和脱氧古洛糖霉素的D-异构体和L-异构体，总收率分别为48％和66％。关键步骤包括使用aza-Achmatowicz反应，非对映选择性Luche还原，非对映选择性二羟基化和串联Cbz脱保护/还原胺化。
• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.