(R)-3-[1-phenyl-2-(trimethylsilyl)ethyl]-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-[1-phenyl-2-(trimethylsilyl)ethyl]-1H-indole
• 英文别名: [(2R)-2-(1H-indol-3-yl)-2-phenylethyl]-trimethylsilane
• 化学式: C₁₉H₂₃NSi
• 分子量: 293.484
• InChiKey: GQMRPEHLJZZFEY-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(trimethylsilyl)ethanone 在 iron perchlorate hexahydrate 、 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (R)-3-[1-phenyl-2-(trimethylsilyl)ethyl]-1H-indole
  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

• 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.