1-(4-methoxyphenyl)-2-trimethylsilylethanol | 138351-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-2-trimethylsilylethanol
• CAS: 138351-84-5
• 化学式: C₁₂H₂₀O₂Si
• 分子量: 224.375
• InChiKey: YDXDCFWLHAJOIA-UHFFFAOYSA-N

物化性质

• 沸点：
  314.2±32.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  吲哚 、 1-(4-methoxyphenyl)-2-trimethylsilylethanol 在 iron perchlorate hexahydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以76%的产率得到
  参考文献：
  名称：

  Development of Solvent-Driven Iron-Catalyzed Reactions

  摘要：

  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.

  DOI：

  10.3987/rev-16-842
• 作为产物：
  描述：

  2-(p-methoxyphenyl)-2-(trimethylsilyl)ethyl trifluoroacetate 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(4-methoxyphenyl)-2-trimethylsilylethanol
  参考文献：
  名称：

  Silicon Effects. V. .BETA.-Silicon Effect in the Solvolysis of 2-Phenylethyl Compounds.

  摘要：

  在 25°C 的各种溶剂中测量了 2-芳基-2-(三甲基硅基)乙基化合物 ArCH(SiMe3)CH2X (4: X = Cl 和 OCOCF3; Ar = C6H5 和 p-MeOC6H4)的溶解速率。氯化物 4（X=Cl；Ar=C6H5）在二噁烷水溶液中的溶解度 m 值为 0.90，与决定速率的电离相一致；在乙醇中生成了（2-乙氧基-2-苯基乙基）三甲基硅烷和苯乙烯，表明在溶解过程中发生了 1，2-SiMe3 迁移。在三氟乙酸盐中测出的 p-MeO 取代效应（kp-MeO/kH）为 2.1，而在 1-芳基-2-（三甲基硅基）乙基化合物 (1) 的溶解过程中观察到的系数为 269，这表明 1 和 4 这两个异构体系统的电离过程涉及不同的中间产物。

  DOI：

  10.1246/bcsj.66.153

文献信息

• Tris(trimethylsilylmethyl)alane: an aldehyde selective peterson methylenation reagent
  作者：Vahak Abedi、Merle A. Battiste

  DOI：10.1016/j.jorganchem.2004.02.009

  日期：2004.5

  Tris(trimethylsilylmethyl)alane (TTMA) is a rapid, efficient, and highly aldehyde-selective trimethylsilylmethylating reagent. A solid lithium halide complex of the reagent, TTMA · 3LiBr (TTMAs), is particularly effective in this transformation to the Peterson alcohol intermediate.

  三（三甲基甲硅烷基甲基）烷烃（TTMA）是一种快速，高效且对醛具有高选择性的三甲基甲硅烷基甲基化试剂。试剂TTMA 3LiBr（TTMAs）的固态卤化锂络合物在向彼得森醇中间体的这种转化中特别有效。
• Taylor, Roger, Journal of the Chemical Society. Perkin transactions II, 1991, # 11, p. 1703 - 1706
  作者：Taylor, Roger

  DOI：——

  日期：——