2,4-di-(tert-butyldimethylsilyloxy)-6-hydroxybenzaldehyde | 233751-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-di-(tert-butyldimethylsilyloxy)-6-hydroxybenzaldehyde
• 英文别名: 4,6-di-tert-butyldimethylsilyloxy-2-hydroxybenzaldehyde；3,5-bis((tert-butyldimethylsilyl)oxy)-2-hydroxybenzaldehyde；2,4-Bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxybenzaldehyde
• CAS: 233751-75-2
• 化学式: C₁₉H₃₄O₄Si₂
• 分子量: 382.648
• InChiKey: LZYXFXFXTWGXHE-UHFFFAOYSA-N

物化性质

• 沸点：
  392.1±42.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-di-(tert-butyldimethylsilyloxy)-6-hydroxybenzaldehyde 在 三异丙氧基氯化钛 、 氢氧化钾 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 20.58h， 生成 (1R,2R,10S,11R,13R)-6,8-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[N-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbutan-2-yl]-S-(4-methylphenyl)sulfonimidoyl]methyl]-14,14-dimethyl-3-oxatetracyclo[11.1.1.02,11.04,9]pentadeca-4(9),5,7-trien-10-ol
  参考文献：
  名称：

  不对称合成中的金属化 2-烯基亚砜亚胺：高度取代的氧杂二环醚的区域和立体选择性合成以及对 Euglobals G1 和 G2 和 Arenaran A 的全合成的研究

  摘要：

  2-环戊烯基-和2-环己烯基甲基亚砜亚胺可以转化为有角碳官能化、高度取代、异构纯（ds≥98%）的2-氧杂双环[3.3.0]辛烷和2-氧杂双环[3.4.0]壬烷。通过方便的一锅序列产生产量。诸如此类的分子框架可以在许多具有生物活性的天然产物中找到。除了方法论工作外，我们还报告了对 euglobals G1 和 G2 以及 arenaran A 的全合成的研究。

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1011::aid-ejoc1011>3.0.co;2-h
• 作为产物：
  描述：

  间苯三酚甲醛 在 咪唑 作用下， 以 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2,4-di-(tert-butyldimethylsilyloxy)-6-hydroxybenzaldehyde
  参考文献：
  名称：

  Selective Cleavage of tert-Butyldimethylsilylethers ortho to a Carbonyl Group by Ultrasound

  摘要：

  A general method for the selective cleavage of tert-butyldimethylsilylethers ortho to a carbonyl group is established by sonication of a 0.1 M solution of the substrate in 1/1 (v/v) CH3OH/CCl4. Other phenolic tert-butyldimethylsilylethers are unaffected. This reaction performed on flavanoids is completed within 3 h and no special workup is required. Other substrates are also investigated and a mechanism is proposed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00053-3

文献信息

• Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups
  作者：Lauren M. Fleury、Joseph B. Gianino、Brandon L. Ashfeld

  DOI：10.1016/j.tetlet.2012.07.103

  日期：2012.10

  A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available (ZnX2)-X-II salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (<= 96%), and a wide assortment of protecting groups was readily removed under the reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• Selective Cleavage of tert-Butyldimethylsilylethers ortho to a Carbonyl Group by Ultrasound
  作者：Alex H De Groot、Roger A Dommisse、Guy L Lemière

  DOI：10.1016/s0040-4020(00)00053-3

  日期：2000.3

  A general method for the selective cleavage of tert-butyldimethylsilylethers ortho to a carbonyl group is established by sonication of a 0.1 M solution of the substrate in 1/1 (v/v) CH3OH/CCl4. Other phenolic tert-butyldimethylsilylethers are unaffected. This reaction performed on flavanoids is completed within 3 h and no special workup is required. Other substrates are also investigated and a mechanism is proposed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Metallated 2-Alkenyl Sulfoximines in Asymmetric Synthesis: Regio- and Stereoselective Synthesis of Highly Substituted Oxabicyclic Ethers and Studies Towards the Total Syntheses of the Euglobals G1 and G2 and Arenaran A
  作者：Michael Reggelin、Matthias Gerlach、Melanie Vogt

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1011::aid-ejoc1011>3.0.co;2-h

  日期：1999.5

  angular carbon-functionalised, highly substituted, isomerically pure (ds ≥ 98%) 2-oxabicyclo[3.3.0]octanes and 2-oxabicyclo[3.4.0]nonanes in high yields by a convenient one-pot sequence. Molecular frameworks such as these can be found in many biologically active natural products. In addition to the methodological work, we report on studies towards the total synthesis of the euglobals G1 and G2 and arenaran

  2-环戊烯基-和2-环己烯基甲基亚砜亚胺可以转化为有角碳官能化、高度取代、异构纯（ds≥98%）的2-氧杂双环[3.3.0]辛烷和2-氧杂双环[3.4.0]壬烷。通过方便的一锅序列产生产量。诸如此类的分子框架可以在许多具有生物活性的天然产物中找到。除了方法论工作外，我们还报告了对 euglobals G1 和 G2 以及 arenaran A 的全合成的研究。