2-(tert-butyldimethylsilanyloxy)-benzoyl chloride | 827575-54-2

• 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: 2-(tert-butyldimethylsilanyloxy)-benzoyl chloride
• 英文别名: 2-((tert-butyldimethylsilyl)oxy)benzoyl chloride；Benzoyl chloride, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-；2-[tert-butyl(dimethyl)silyl]oxybenzoyl chloride
• CAS: 827575-54-2
• 化学式: C₁₃H₁₉ClO₂Si
• 分子量: 270.831
• InChiKey: ONJRYFPZAIDZCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-(tert-butyldimethylsilanyloxy)-benzoyl chloride 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二乙胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 39.0h， 生成 黄酮
  参考文献：
  名称：

  Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries

  摘要：

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00279-8
• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-((tert-butyldimethylsilyl)oxy)benzoate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(tert-butyldimethylsilanyloxy)-benzoyl chloride
  参考文献：
  名称：

  Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries

  摘要：

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00279-8

文献信息

• Functionalization and Rearrangement of Spirocyclohexadienyl Oxindoles: Experimental and Theoretical Investigations
  作者：Géraldine Rousseau、Frédéric Robert、Yannick Landais

  DOI：10.1002/chem.200901434

  日期：2009.10.26

  aldehydes. Interestingly, alkylation and hydroxyalkylation occurred with different regiocontrol. DFT calculations were performed that rationalize the observed skeleton rearrangement, emphasizing the role of LDA/diisopropylamine in this rearrangement. The proposed mechanism thus relies on a thermodynamically driven diisopropylamine‐mediated proton transfer with the cleavage of the diene–amide CO bond

  介绍了螺环己基2,5-二烯恶吲哚的制备和功能化。标题化合物的螺环核心是通过SmI 2介导的芳基碘代苯甲酰胺的环化反应而安装的。然后用CF 3 CO 3 H进行环氧化，并显示出高水平的非对映异构控制：该试剂接近二烯部分合成酰胺基上的氢键很可能是由于酰胺的CO键和过酸氢之间存在氢键所致。然后检查了螺环己基2,5-二烯恶吲哚的碳负离子官能化，从而将应变的螺环系统空前地重排为脱芳香族化的菲啶酮。在-40°C下用二异丙基氨基化锂（LDA）处理后，二烯重排以提供一个菲啶酮锂烯醇盐中间体，该中间体被亲电子试剂（包括卤代烷和醛）捕获。有趣的是，在不同的区域控制下发生烷基化和羟烷基化。进行DFT计算以合理化观察到的骨架重排，强调LDA /二异丙胺在这种重排中的作用。
• Rearrangement of Spirocyclic Oxindoles with Lithium Amide Bases
  作者：Géraldine Rousseau、Frédéric Robert、Kurt Schenk、Yannick Landais

  DOI：10.1021/ol8016885

  日期：2008.10.16

  Spirocyclohexa-2,5-dienes were shown to rearrange at -40 degrees C, when treated with 1 equiv of LDA. Alkyl halides and aldehydes then reacted with the resulting phenanthridinone lithium enolate intermediates, with distinct regioselectivities and high diastereocontrol, to afford functionalized dearomatized phenanthridinones which were elaborated further. A mechanistic scheme involving a diisopropylamine-mediated

  当用1当量的LDA处理时，螺环己基2，5-二烯显示在-40℃下重排。然后使烷基卤化物和醛与所生成的菲啶酮酮烯酸锂中间体反应，具有独特的区域选择性和高非对映异构控制性，从而提供了功能化的脱芳构菲咯烷酮，并对其进行了进一步的阐述。提出了涉及二异丙胺介导的质子转移的机制方案以合理化重排。
• Pt(II) or Ag(I) Salt Catalyzed Cycloisomerizations and Tandem Cycloadditions Forming Functionalized Azacyclic Arrays
  作者：Tyler J. Harrison、Gregory R. Dake

  DOI：10.1021/ol047696b

  日期：2004.12.1

  Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH](2)(BF4)(2)) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.
• WO2023/40937
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries
  作者：Abhijit S. Bhat、Jennifer L. Whetstone、Robert W. Brueggemeier

  DOI：10.1016/s0040-4039(99)00279-8

  日期：1999.3

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.