3,4-bis[(trimethylsilyl)oxy]benzoic acid (trimethylsilyl) ester | 2347-40-2

• 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: 3,4-bis[(trimethylsilyl)oxy]benzoic acid (trimethylsilyl) ester
• 英文别名: ditrimethylsilylprotocatechuic acid；3.4-Dihydroxibenzoesaeuretrimethylsilylester-di-trimethylsilylether；Trimethylsilyl 3,4-bis(trimethylsilyloxy)benzoate
• CAS: 2347-40-2
• 化学式: C₁₆H₃₀O₄Si₃
• 分子量: 370.668
• InChiKey: DVAGRNBRUDZPDF-UHFFFAOYSA-N

物化性质

• 保留指数：
  1826;1826;1826;1828

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  槲皮素 在 β-cyclodextrin 、 potassium chloride 、 potassium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 3,4-bis[(trimethylsilyl)oxy]benzoic acid (trimethylsilyl) ester
  参考文献：
  名称：

  The influence of the host–guest interaction on the oxidation of natural flavonoid dyes

  摘要：

  研究了分子空腔保护对作为古老挂毯原始染料的生物有机化合物槲皮素和芦丁的降解过程的影响。降解过程通过在水介质中的电化学方法进行研究。通过气相色谱-质谱分析分离和鉴定了电解的产物。循环伏安特性表明形成了包含复合物。包含影响了与类黄酮分子不同解离形式相关的氧化波的氧化还原电位。结果表明，由槲皮素氧化形成的分解产物在β-环糊精的空腔中稳定，包括主要氧化产物2(3′,4′-二羟基苯甲酰)-2,4,6-三羟基苯并呋喃-3(2H)-酮。芦丁与β-环糊精的1:1包含复合物的形成得到了荧光强度增强的支持。对于槲皮素，当与β-环糊精形成1:1包含复合物时，荧光强度会降低。

  DOI：

  10.1135/cccc2011106

文献信息

• Partition coefficients of ketones, phenols, aliphatic and aromatic acids, and esters in n-hexane/nitromethane
  作者：Urszula Kotowska、Valery Isidorov

  DOI：10.2478/s11532-011-0060-4

  日期：2011.10.1

  in sample preparation and in countercurrent and liquid-liquid chromatographic separations. Partition coefficients are widely used in toxicology, environmental, and analytical chemistry. The K hn determination procedure for the n -hexane/nitromethane system was optimized and partition coefficients for 99 ketones, esters and trimethylsilyl derivatives of phenols, aliphatic and aromatic acids were determined

  液-液分配用于样品制备以及逆流和液-液色谱分离。分配系数被广泛用于毒理学，环境和分析化学中。该 ķ HN 用于确定过程 Ñ 正己烷/硝基甲烷体系进行了优化和分配系数为99酮，酯和酚的三甲基甲硅烷衍生物，测定脂族和芳族酸。对于130种化合物， 使用 K hn 与其他理化和结构参数之间的数学关系来预测 K hn 值 。
• P.M.R. Spectroscopy of Trimethylsilyl Derivatives of Hydroxy Acids
  作者：Guy Gordon Studdy Dutton、Norman Funnell、Kelly Blair Gibney

  DOI：10.1139/v72-616

  日期：1972.12.1

  P.m.r. spectroscopy at 60 MHz of trimethylsilyl ethers and esters, prepared from hydroxy acids, gives well resolved sharp singlets in the range τ 9.8–9.9, These signals may be used to determine the ratio of hydroxyl to carboxyl groups in a molecule. Measurements may be made directly on fractions isolated by gas–liquid chromatography. The influence of the solvent on the resolution is demonstrated.

  由羟基酸制备的三甲基甲硅烷基醚和酯在 60 MHz 下的 Pmr 光谱在 τ 9.8-9.9 范围内得到很好分辨的尖锐单峰。这些信号可用于确定分子中羟基与羧基的比率。可以直接对通过气液色谱分离的馏分进行测量。证明了溶剂对分辨率的影响。
• Schraml, Jan; Past, Jaan; Puskar, Jueri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 8, p. 1985 - 1991
  作者：Schraml, Jan、Past, Jaan、Puskar, Jueri、Pehk, Tonis、Lippmaa, Endel、Brezny, Robert

  DOI：——

  日期：——
• Characterization of Phenolic Compounds in Rooibos Tea
  作者：Nicole Krafczyk、Marcus A. Glomb

  DOI：10.1021/jf703701n

  日期：2008.5.1

  Polyphenols present in rooibos, a popular herbal tea from Aspalathus linearis, were isolated in two steps. First, phenolic ingredients were separated by multilayer countercurrent chromatography (MLCCC). Preparative high-performance liquid chromatography (HPLC) was then applied to obtain pure flavonoids. The purity and identity of isolated compounds was confirmed by different NMR experiments, HPLC-diode array detector (DAD), or gas chromatography-mass spectrometry (GCMS) analysis. This strategy proved to be valid to isolate material in up to gram quantities and to verify known and previously not published polyphenol structures. In addition the chemistry of dihydrochalcones and related intermediates was studied. The dihydrochalcone aspalathin was oxidized to the corresponding flavanone-C-glycosides ((R)/(S)-eriodictyol-6-C-beta-D-glucopyranoside and (R)/(S)-eriodictyol-8-C-beta-D-glucopyranoside). Flavanone-6-C-beta-D-glucopyranosides were further degraded to flavones isoorientin and orientin.
• The influence of the host–guest interaction on the oxidation of natural flavonoid dyes
  作者：Šárka Ramešová、Romana Sokolová、Ilaria Degano、Magdaléna Hromadová、Miroslav Gál、Viliam Kolivoška、Maria Perla Colombini

  DOI：10.1135/cccc2011106

  日期：——

  The influence of the molecular cavity protection on degradation processes of bioorganic compounds quercetin and luteolin used as the original dyes in old tapestries was studied. The degradation processes were studied by electrochemical methods in aqueous media. The products of the exhaustive electrolysis were separated and identified by GC-MS analysis. Cyclic voltammetry characteristics indicate that the inclusion complex is formed. The inclusion affects the redox potentials of both oxidation waves related to the different dissociation forms of the flavonoid molecule. It was shown that decomposition products formed by the oxidation of quercetin are stabilized in the cavity of β-cyclodextrin, including the main oxidation product 2(3′,4′-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one. The formation of the 1:1 inclusion complex of luteolin with β-cyclodextrin is supported by the enhancement of fluorescence intensity. In the case of quercetin, a decrease of fluorescence intensity occurs when 1:1 inclusion complex with β-cyclodextrin is formed.

  研究了分子空腔保护对作为古老挂毯原始染料的生物有机化合物槲皮素和芦丁的降解过程的影响。降解过程通过在水介质中的电化学方法进行研究。通过气相色谱-质谱分析分离和鉴定了电解的产物。循环伏安特性表明形成了包含复合物。包含影响了与类黄酮分子不同解离形式相关的氧化波的氧化还原电位。结果表明，由槲皮素氧化形成的分解产物在β-环糊精的空腔中稳定，包括主要氧化产物2(3′,4′-二羟基苯甲酰)-2,4,6-三羟基苯并呋喃-3(2H)-酮。芦丁与β-环糊精的1:1包含复合物的形成得到了荧光强度增强的支持。对于槲皮素，当与β-环糊精形成1:1包含复合物时，荧光强度会降低。

表征谱图