O,O'-bis(tert-butyldimethylsilyl)catechol | 153185-80-9

• 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: O,O'-bis(tert-butyldimethylsilyl)catechol
• 英文别名: 1,2-bis((tert-butyldimethylsilyl)oxy)benzene；Catechol, 2TBDMS derivative；tert-butyl-[2-[tert-butyl(dimethyl)silyl]oxyphenoxy]-dimethylsilane
• CAS: 153185-80-9
• 化学式: C₁₈H₃₄O₂Si₂
• 分子量: 338.638
• InChiKey: MXBBMBQKOKWYOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±15.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)
• 保留指数：
  1779.5

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  O,O'-bis(tert-butyldimethylsilyl)catechol 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 potassium fluoride 、 四(三苯基膦)钯 、 氢溴酸 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 环己乙酸,2-甲基-5-(1-甲基乙基)-,乙基酯
  参考文献：
  名称：

  A concise synthesis of rooperol and related 1,5-diarylpent-1-en-4-ynes

  摘要：

  Two powerful strategies: rapid construction of allylic alkynoates via cyclopropenium ion chemistry and mild, palladium-catalyzed decarboxylative coupling were employed in a concise, 5-steps synthesis of the natural product rooperol. The overall approach allows the preparation of rooperol analogs in as few as 3 steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.138
• 作为产物：
  描述：

  tert-butyl-[(1S,6R)-6-[tert-butyl(dimethyl)silyl]oxycyclohexa-2,4-dien-1-yl]oxy-dimethylsilane 在 氧气 作用下， 生成 O,O'-bis(tert-butyldimethylsilyl)catechol
  参考文献：
  名称：

  Photochemical routes from arenes to inositol intermediates: The photo-oxidation of substituted cis-cyclohexa-3,5-diene-1,2-diols

  摘要：

  DOI：

  10.1016/s0040-4039(00)99416-4

文献信息

• Highly Efficient and Convenient Methods for the Direct Conversion of Aryl Silyl Ethers and Aryl Acetates into Aryl Alkyl Ethers
  作者：Takeshi Oriyama、Kojiro Noda、Kaori Yatabe

  DOI：10.1055/s-1997-3267

  日期：1997.6

  Direct conversion of aryl trialkylsilyl ethers and aryl acetates into the corresponding alkyl-protected phenols such as benzyl and allyl ethers can be conveniently performed by the reaction with alkyl halide in the presence of cesium fluoride and sodium methoxide, respectively, in a one-pot procedure.

  芳基三烷基硅醚和芳基乙酸酯可以直接转换为相应的烷基保护酚类化合物，如苄基和烯丙基醚，这一过程可以通过在一个反应釜内分别使用氟化铯和甲醇钠与烷基卤化物的反应来方便地实现。
• Highly Active Multidentate Catalysts for Efficient Alkyne Metathesis
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US20130261295A1

  公开（公告）日：2013-10-03

  The invention relates to highly active and selective catalysts for alkyne metathesis. In one aspect, the invention includes a multidentate organic ligand wherein one substrate-binding site of the metal center is blocked. In another aspect, the invention includes N-quaternized or silane-based multidentate organic ligands, capable of binding to metals. In yet another aspect, the invention includes N-quaternized or silane-based multidentate catalysts. The catalysts of the invention show high robustness, strong resistance to small alkyne polymerization and significantly enhanced catalytic activity compared to their corresponding non-quaternized or non-silane-based multidentate catalyst analogues.

  该发明涉及用于炔烃交换反应的高活性和选择性催化剂。在一个方面，该发明包括一种多齿有机配体，其中金属中心的一个底物结合位点被阻塞。在另一个方面，该发明包括N-季铵化或硅基多齿有机配体，能够与金属结合。在另一个方面，该发明包括N-季铵化或硅基多齿催化剂。该发明的催化剂表现出高稳定性，对小炔烃聚合具有很强的抵抗力，并且与其对应的非季铵化或非硅基多齿催化剂类似物相比，具有显着增强的催化活性。
• Multidentate Triphenolsilane-Based Alkyne Metathesis Catalysts
  作者：Haishen Yang、Zhenning Liu、Wei Zhang

  DOI：10.1002/adsc.201201105

  日期：2013.3.25

  propylidyne catalysts has been developed, which are resistant to small alkyne polymerization and compatible with various functional groups (including phenol substrates). The catalysts remain active in solution for days at room temperature (months at −30 °C). The catalysts are also compatible with 5 Å molecular sieves (small alkyne scavengers), and have enabled the homodimerization of small alkyne substrates

  已经开发了一系列三酚硅烷配位的钼（VI）丙炔催化剂，该催化剂可抵抗小型炔烃聚合反应并与各种官能团（包括酚底物）兼容。催化剂在室温下在溶液中保持活性数天（在-30°C时数月）。该催化剂还与5Å分子筛（小型炔烃清除剂）兼容，并能够在封闭系统中于40–70°C下使小型炔烃底物均二聚，二聚体产物的收率达76–96％。还以克级制备了形状持久的亚芳基亚炔基大环（11），催化剂负载量为0.5 mol％，几乎可以定量收率。
• An approach to metal-assisted DNA base pairing: novel β-C-nucleosides with a 2-aminophenol or a catechol as the nucleobase
  作者：Kentaro Tanaka、Motoyuki Tasaka、Honghua Cao、Mitsuhiko Shionoya

  DOI：10.1016/s0928-0987(00)00210-4

  日期：2001.4

  coordination in the base pairing, thereby creating a novel hybridization motif in duplex DNA. In this regard, we have further designed two types of artificial beta-C-nucleosides possessing a metal-chelating site (a 2-aminophenol or a catechol) as the nucleobase moiety. These artificial nucleosides are directed toward controlling the net charges of the metal-assisted base pairs. This paper describes

  先前发现，具有苯二胺部分作为核碱基的金属螯合β-C-核苷可与Pd（2+）离子在水性介质中形成稳定的2：1络合物，其中氢键被碱中的金属配位取代配对，从而在双链体DNA中产生新的杂交基序。在这方面，我们进一步设计了两种具有金属螯合位点（2-氨基苯酚或邻苯二酚）作为核碱基部分的人工β-C-核苷。这些人工核苷旨在控制金属辅助碱基对的净电荷。本文描述了带有2-氨基苯酚或邻苯二酚部分的人工核苷的便捷合成方法。每个核苷通过2'直接合成
• An Effective Approach for the Silylation of Hydroxyl Compounds in Room Temperature Ionic Liquids
  作者：Zhen-Yuan Xu、Dan-Qian Xu、Bao-You Liu、Shu-Ping Luo

  DOI：10.1081/scc-120026356

  日期：2003.12.1

  The room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate (BMImPF(6)) is used as a "green" recyclable. alternative to conventional solvents for the silylation of a series of hydroxyl compounds (alcohols and phenols) with t-butyidimethylchlorosilane (TBDMCS), which has some advantages such as simplicity of the synthetic procedure, the potential for recycling of the ionic liquid and the environmentally benign.