3-(tert-butyldimethylsilyloxy)-2,6-dimethylbenzaldehyde | 1357476-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(tert-butyldimethylsilyloxy)-2,6-dimethylbenzaldehyde
• 英文别名: 3-[Tert-butyl(dimethyl)silyl]oxy-2,6-dimethylbenzaldehyde
• CAS: 1357476-71-1
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: XRENHIQUDGBKJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±30.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilyloxy)-2,6-dimethylbenzaldehyde 在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 碘 、 硝酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 3-[ethoxy(3-isopropyl-4,5-dimethoxyphenyl)methyl]-2,4-dimethylphenol
  参考文献：
  名称：

  Synthetic Approach to 4a-Methyltetrahydrofluorene-Type Diterpenoids via an Aromatic Oxidation of Phenol Derivatives

  摘要：

  An intramolecular aromatic oxidation of a phenolic compound with a hypervalent iodine reagent afforded the coupling product, in which the coupling took place at the para-position of the methoxy goup of the starting material instead of the desired para-position of the isopropenyl group, unfortunately.

  DOI：

  10.1080/00397911.2010.518274
• 作为产物：
  描述：

  methyl 3-hydroxy-2,6-dimethylbenzoate 在 咪唑 、 重铬酸吡啶 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-(tert-butyldimethylsilyloxy)-2,6-dimethylbenzaldehyde
  参考文献：
  名称：

  Synthetic Approach to 4a-Methyltetrahydrofluorene-Type Diterpenoids via an Aromatic Oxidation of Phenol Derivatives

  摘要：

  An intramolecular aromatic oxidation of a phenolic compound with a hypervalent iodine reagent afforded the coupling product, in which the coupling took place at the para-position of the methoxy goup of the starting material instead of the desired para-position of the isopropenyl group, unfortunately.

  DOI：

  10.1080/00397911.2010.518274

文献信息

• Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
  作者：Kang Du、Pan Guo、Yuan Chen、Zhen Cao、Zheng Wang、Wenjun Tang

  DOI：10.1002/anie.201411817

  日期：2015.3.2

  efficient construction of a series of chiral phenanthrenone derivatives bearing an all‐carbon quaternary center. The effectiveness of this method in the synthesis of terpenes and steroids was demonstrated by a highly efficient synthesis of a kaurene intermediate, the facile construction of the skeleton of the anabolic steroid boldenone, and the enantioselective total synthesis of the antimicrobial diterpene

  为了有效构建一系列带有全碳四元中心的手性菲咯酮衍生物，开发了一种新颖的对映选择性钯催化的脱芳香环化反应。该方法在萜烯和类固醇合成中的有效性通过高效合成天竺葵中间体，合成代谢类固醇马来烯酮骨架的简便构建以及抗菌二萜天然产物（-）的对映选择性全合成得到了证明。雌二醇。
• Synthetic Approach to 4a-Methyltetrahydrofluorene-Type Diterpenoids via an Aromatic Oxidation of Phenol Derivatives
  作者：Wuhong Chen、Koichi Kobayashi、Kazunori Takahashi、Toshio Honda

  DOI：10.1080/00397911.2010.518274

  日期：2011.11.15

  An intramolecular aromatic oxidation of a phenolic compound with a hypervalent iodine reagent afforded the coupling product, in which the coupling took place at the para-position of the methoxy goup of the starting material instead of the desired para-position of the isopropenyl group, unfortunately.