4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone | 108956-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone
• 英文别名: di tert-butyldimethylsilyloxy-2',4'-hydroxy-6' acetophenone；1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one；2,4-O-bis(tert-butyldimethylsilyl)phloracetophenone；2',4'-O-bis(tert-butyldimethylsilyl)-6'-hydroxyacetophenone；1-[2,4-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxyphenyl]ethanone；1-[2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxyphenyl]ethanone
• CAS: 108956-90-7
• 化学式: C₂₀H₃₆O₄Si₂
• 分子量: 396.674
• InChiKey: VSEXTNRATPGFEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone 在 硫酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 72.0h， 生成 苜蓿素
  参考文献：
  名称：

  Increased Bioavailability of Tricin−Amino Acid Derivatives via a Prodrug Approach

  摘要：

  Tricin (4',5,7-trihydroxy-3',5'-dimethoxyflavone) has demonstrated diverse biological activities. This compound has a high anti-human cytomegalovirus (HCMV) activity; however, its oral availability is low. To improve its bioavailability, we synthesized tricin-amino acid derivatives as prodrugs and investigated their cell permeability, stability in vitro, and oral availability in vivo. The results demonstrated that the tricin-alanine-glutamic acid conjugate exhibited enhanced permeability, stability in MDCK cells, and excellent bioavailability after oral administration in Crl:CD (SD) male rats. Tricin-alanine-glutamic acid conjugate is a potential new anti-HCMV drug.

  DOI：

  10.1021/jm1015457
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone
  参考文献：
  名称：

  Rottlerin的马赛克：续集。

  摘要：

  Rottlerin（1）是一种有效的蛋白激酶Cδ抑制剂，具有广泛的生物学活性。然而，该分子被开发为药物的潜力受到其有限可用性的限制。我们在这里报告了可在2天内完成的五步合成路线中克级定量的rottlerin合成。关键的氨基亚甲基中间体（15）与各种富电子芳烃的反应扩展了该方法，形成了新的不对称亚甲基桥连化合物。X射线晶体结构首次揭示了这种分子的飞旋镖形状。首次观察到了rottlerin（1）直接转化为天然产物isorottlerin（35），我们将这种转化称为“ isorottlerin变化”。此外，检查了rottlerin（1）和新的rottlerin类似物32-34对金黄色葡萄球菌的抗菌活性。这些化合物的MIC值低至2.0μM，与临床使用的抗生素庆大霉素相当。

  DOI：

  10.1021/acs.jnatprod.8b00917

文献信息

• Total synthesis of acylphloroglucinols and their antibacterial activities against clinical isolates of multi-drug resistant (MDR) and methicillin-resistant strains of Staphylococcus aureus
  作者：M. Mukhlesur Rahman、Winnie K.P. Shiu、Simon Gibbons、John P. Malkinson

  DOI：10.1016/j.ejmech.2018.05.038

  日期：2018.7

  of olympicin A prompted us to carry out the total synthesis of 6 and a series of analogues in order to assess their structure-activity profile as a new group of antibacterial agents. Following the synthesis of 6 and structurally-related acylphloroglucinols 7–15 and 18–24, their antibacterial activities against a panel of S. aureus strains were evaluated. The presence of an alkyloxy group consisting

  以生物测定为导向的药物发现工作着眼于金丝桃属的各种物种，导致发现了许多新的酰基间苯三酚，包括（S，E）-1-（2-（（3,7-dimethylocta-2,6-dien-来自H的1-基）氧基）-4,6-二羟基苯基）-2-甲基丁-1--1-酮（6，奥比汀A）。olympicum，与MIC值范围为0.5至1mg / L与一系列多药耐药（MDR）和耐甲氧西林的临床分离株的金黄色葡萄球菌（MRSA）菌株。奥林匹克霉素A的有前途的活性和有趣的化学反应促使我们进行6的全合成以及一系列类似物，以评估它们作为一组新的抗菌剂的结构活性特征。以下的合成6和结构上相关的acylphloroglucinols 7 - 15和18 - 24，其对一组抗细菌活性的金黄色葡萄球菌菌株进行评价。在间苯三酚核心上，由一个8至10个碳原子邻位至一个5个碳原子的酰基取代基组成的烷氧基的存在是重要的结构特征，有望实现抗葡萄球菌的活性。
• Cottet, Francoise; Cottier, Louis; Descotes, Gerard, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1481 - 1486
  作者：Cottet, Francoise、Cottier, Louis、Descotes, Gerard、Srivastava, Rajendra Mohan

  DOI：——

  日期：——
• Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Paul Beckett、Hagen Schroeter

  DOI：10.1016/j.tetasy.2013.02.012

  日期：2013.4

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.
• A Regiodivergent Synthesis of Ring A C-Prenylflavones
  作者：Alberto Minassi、Anna Giana、Abdellah Ech-Chahad、Giovanni Appendino

  DOI：10.1021/ol800665w

  日期：2008.6.5

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.
• Mahling, Juergen-Andreas; Jung, Karl-Heinz; Schmidt, Richard R., Liebigs Annalen, 1995, # 3, p. 461 - 466
  作者：Mahling, Juergen-Andreas、Jung, Karl-Heinz、Schmidt, Richard R.

  DOI：——

  日期：——