1-(allyloxy)-3-(tert-butyldimethylsiloxy)benzene | 132802-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(allyloxy)-3-(tert-butyldimethylsiloxy)benzene
• 英文别名: 1-(tert-Butyldimethylsiloxy)-3-(allyloxy)benzene；1-allyloxy-3-tert-butyldimethylsilyloxybenzene；Tert-butyl-dimethyl-(3-prop-2-enoxyphenoxy)silane
• CAS: 132802-62-1
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: FELJKUYSBJAIKK-UHFFFAOYSA-N

物化性质

• 沸点：
  300.5±25.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(allyloxy)-3-(tert-butyldimethylsiloxy)benzene 在 氯化二乙基铝 作用下， 生成
  参考文献：
  名称：

  A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols

  摘要：

  Oxidation of p-methoxy-substituted phenols with iodobenzene bis-trifluoroacetate in the presence of electron-rich styrene derivatives affords trans-dihydrobenzofurans stereoselectively.

  DOI：

  10.1021/jo00006a003
• 作为产物：
  描述：

  3-allyloxyphenol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到1-(allyloxy)-3-(tert-butyldimethylsiloxy)benzene
  参考文献：
  名称：

  Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives

  摘要：

  Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative. The yield of product in this electrochemical oxidation depends upon the ratio of phenol to styrene derivative, current density, and to a lesser extent the amount of supporting electrolyte. While p-methoxyphenol and 4-methoxy-3-methylphenol give good yields of the dihydrobenzofurans using 1:1 molar ratio of reactants, 3,4-dimethoxyphenol requires a 3-4 molar excess of the styrene derivative for a comparable yield of product. Although 4-methoxy-1-naphthol shows yields comparable to p-methoxyphenol in the anodic cycloaddition reaction, 1- and 2-naphthol gave very low yields of product. Qualitatively, trans- and cis-1,2-dimethoxy-4-propenylbenzene show similar yields in the cycloaddition reaction. Many of these same substrates were examined using iodobenzene bis(trifluoroacetate) as oxidant, and the same products were formed as in the electrochemical oxidations noted above. However, for the reaction of 2-naphthol and 1,2-dimethoxy-4-propenylbenzene the iodobenzene bis(trifluoroacetate) oxidation gave a much better yield of the product. A mechanism involving reaction of a phenoxy radical-styrene radical cation pair is considered and discussed.

  DOI：

  10.1021/jo00033a040

文献信息

• Boron Trichloride Mediated Regioselective Claisen Rearrangement of Resorcinol­ Derivatives: Application to Resorcinol Carvonyl Ethers
  作者：Takuya Kumamoto、Fumihiro Ito、Keiko Fusegi、Tsutomu Ishikawa

  DOI：10.1055/s-2007-983712

  日期：2007.6

  Claisen rearrangement (CR) of resorcinol allyl ethers was examined. Although thermal CR gave low regioselectivity, the selectivity was much improved in the presence of a Lewis acid such as boron trichloride. This rearrangement was successfully applied to resorcinol carvonyl ethers for the regioselective introduction of a carvone unit into the resorcinol skeleton for the synthesis of phytoestrogenic

  检测了间苯二酚烯丙基醚的克莱森重排 (CR)。尽管热 CR 的区域选择性较低，但在路易斯酸（如三氯化硼）存在下，选择性得到了很大改善。这种重排成功地应用于间苯二酚香芹酮醚，用于将香芹酮单元区域选择性地引入间苯二酚骨架，以合成植物雌激素微雌激素。