三乙基(呋喃-2-氧基)硅烷 | 62596-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 三乙基(呋喃-2-氧基)硅烷
• 英文名称: triethyl(furan-2-yloxy)silane
• 英文别名: 2-TESO-furan；triethyl-furan-2-yloxy-silane；Triethyl[(furan-2-yl)oxy]silane
• CAS: 62596-54-7
• 化学式: C₁₀H₁₈O₂Si
• 分子量: 198.337
• InChiKey: YGVPAHRKSAVCPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三乙基(呋喃-2-氧基)硅烷 、 马来酸二乙酯 以 氘代氯仿 为溶剂， 反应 72.0h， 以62%的产率得到
  参考文献：
  名称：

  Dynamics of Diels–Alder reactions involving 2-trialkylsilyloxyfurans

  摘要：

  Increasing the size of the silyl group on 2-trial kylsilyloxyfurans reduces the rate of Diels-Alder reactions with maleic acid derivatives. While the exo-adduct resulted from the reaction between 2-silyloxyfurans and maleic anhydride, endo-adducts resulted from the reactions with maleate esters. Analysis of transition state structures for the cycloaddition, calculated at the B3LYP/6-31G* level of theory, revealed significant stretch-mode asynchronicity in the forming bonds, with selectivity arising from steric interactions that affect torsional strain about the shorter of the forming bonds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.004

文献信息

• 1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid
  作者：Hikaru Yanai、Arata Takahashi、Takeo Taguchi

  DOI：10.1039/c0cc02438d

  日期：——

  In situ-generated silyl methide species (R(3)Si-CTf(2)R') effectively catalyzed the reaction of beta-substituted alpha,beta-unsaturated aldehydes with silicon dienoates such as 3-bromo-2-TESO-furan to give the corresponding gamma-adducts with excellent 1,4-selectivity and good anti selectivity.

  原位生成的甲硅烷基甲基化物物种（R（3）Si-CTf（2）R'）有效催化β-取代的α，β-不饱和醛与硅二烯酸酯如3-溴-2-TESO-呋喃的反应得到具有优异的1,4-选择性和良好的抗选择性的相应的伽玛加合物。
• Highly Effective Vinylogous Mukaiyama−Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane
  作者：Arata Takahashi、Hikaru Yanai、Min Zhang、Takaaki Sonoda、Masaaki Mishima、Takeo Taguchi

  DOI：10.1021/jo902641g

  日期：2010.2.19

  Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) performed as an excellent acid catalyst for the vinylogous Mukaiyama-Michael reaction of alpha,beta-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted gamma-butenolide structure.
• Catalytic Asymmetric Cascade Vinylogous Mukaiyama 1,6-Michael/Michael Addition of 2-Silyloxyfurans with Azoalkenes: Direct Approach to Fused Butyrolactones
  作者：Jun Li、Rong Huang、Yi-Kang Xing、Guofu Qiu、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1021/jacs.5b06509

  日期：2015.8.19

  An unprecedented cascade vinylogous Mukaiyama 1,6-MA/MA of 2-silyloxyfurans and azoalkenes was realized with a Cu(II)/Bu-t-Box complex. An array of fused butyrolactones containing multiple stereocenters was generally obtained in good yield (up to 90% yield) with exclusive diastereoselectivity (>20:1 dr) and excellent enantioselectivity (up to 99% ee). Carbon isotope effects measured by C-13 NMR revealed a stepwise mechanism for this annulation process.