3-methoxy-4-[(trimethylsilyl)-oxy]benzoic acid (trimethylsilyl) ester | 2078-15-1

• 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-methoxy-4-[(trimethylsilyl)-oxy]benzoic acid (trimethylsilyl) ester
• 英文别名: trimethylsilyl-3-methoxy-4-[(trimethylsilyl)oxy]benzoic acid ester；4-trimethylsiloxy-3-methoxy-benzoic acid trimethylsilyl ester；4-Hydroxy-3-methoxybenzoesaeure(TMS)(2)；Benzoic acid, 3-methoxy-4-[(trimethylsilyl)oxy]-, trimethylsilyl ester；trimethylsilyl 3-methoxy-4-trimethylsilyloxybenzoate
• CAS: 2078-15-1
• 化学式: C₁₄H₂₄O₄Si₂
• 分子量: 312.513
• InChiKey: UQZKEPFYTGMPKU-UHFFFAOYSA-N

物化性质

• 保留指数：
  1750;1754;1754;1754;1754;1755;1754;1753

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-[(trimethylsilyl)-oxy]benzoic acid (trimethylsilyl) ester 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-(trimethylsiloxy-3-methoxy)phenyl isocyanate
  参考文献：
  名称：

  Schwarz, Gerd; Alberts, Heinrich; Kricheldorf, Hans R., Liebigs Annalen der Chemie, 1981, # 7, p. 1257 - 1270

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 香草酸 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到3-methoxy-4-[(trimethylsilyl)-oxy]benzoic acid (trimethylsilyl) ester
  参考文献：
  名称：

  Schwarz, Gerd; Alberts, Heinrich; Kricheldorf, Hans R., Liebigs Annalen der Chemie, 1981, # 7, p. 1257 - 1270

  摘要：

  DOI：

文献信息

• Investigation of the Substrate Range of CYP199A4: Modification of the Partition between Hydroxylation and Desaturation Activities by Substrate and Protein Engineering
  作者：Stephen G. Bell、Ruimin Zhou、Wen Yang、Adrian B. H. Tan、Alexander S. Gentleman、Luet-Lok Wong、Weihong Zhou

  DOI：10.1002/chem.201202776

  日期：2012.12.21

  enzyme CYP199A4, from Rhodopseudomonas palustris HaA2, can efficiently demethylate 4‐methoxybenzoic acid. It is also capable of oxidising a range of other related substrates. By investigating substrates with different substituents and ring systems we have been able to show that the carboxylate group and the nature of the ring system and the substituent are all important for optimal substrate binding

  细胞色素P450酶CYP199A4，来自Phodopseudomonas palustrisHaA2可以有效地使4-甲氧基苯甲酸去甲基化。它还能够氧化多种其他相关的底物。通过研究具有不同取代基和环系统的底物，我们已经能够证明羧酸酯基团以及环系统和取代基的性质对于优化底物结合和活性都至关重要。藜芦酸，2-萘甲酸和吲哚-6-羧酸底物结合的CYP199A4复合物的结构揭示了底物的结合模式和活性位点残基的侧链构象变化，以适应这些较大的底物。它们还为产物氧化的选择性提供了理论依据。CYP199A4对烷基取代的苯甲酸的氧化更复杂，去饱和反应与羟基化活性竞争。β Ç 乙基的H键更靠近血红素铁比作为C α（3.5对4.8）。当与反应中间体的相对能量耦合时，该观察结果表明烷基相对于血红素铁的定位对于确定所观察到的去饱和量可能是至关重要的。通过突变CYP199A4（Phe185）活性位点中的单个残基，我们能够将该酶转化为4-乙基苯甲酸去饱和酶。
• 29Si and13C NMR spectra of 4-substituted 2-methoxytrimethylsiloxybenzenes. Factors determining the chemical shifts in models of lignin constituents
  作者：Jan Schraml、Magdalena Kvíčalová、Václav Chvalovský、Thomas Elder、Robert Brežný

  DOI：10.1002/mrc.1260281112

  日期：1990.11

  29Si and 13C NMR chemical shifts are reported for a series of twenty 4‐substituted 2‐methoxytrimethyl‐siloxybenzenes; the set of substituents incorporates a basic set of ten substituents differing in their relative polar and resonance effects and ten other substituents which model substituents encountered in lignins. The factors affecting the chemical shifts are discussed using a comparison with the

  报告了一系列 20 个 4-取代的 2-甲氧基三甲基-甲硅烷氧基苯的 29Si 和 13C NMR 化学位移；这组取代基包含一组基本的十个取代基，它们的相对极性和共振效应不同，以及十个模拟木质素中遇到的取代基的其他取代基。影响化学位移的因素通过与类似系列化合物的 NMR 数据进行比较、与取代基参数的相关性和通过量子化学方法计算的电子电荷（力场优化分子几何的 MNDO 计算）为基本集合进行讨论. 得出的结论是，在三甲基甲硅烷氧基的邻位上的甲氧基在其大部分时间里，甲基位于苯环平面内的构象，与呈垂直构象的三甲基甲硅烷氧基相反。在甲氧基和三甲基甲硅烷氧基上观察到的邻近去屏蔽效应受 4 位取代基的影响，这与这些效应是由于邻位氧原子或其未共享电子的相互作用的观点一致。29Si 化学位移对σpis 的依赖性基本上不受邻甲氧基存在的影响。这与这些效应是由于邻位氧原子或其未共享电子的相互作用的观点一致。29Si
• Metabolic pathways of 4-[(3-methoxyphenyl)methyl]- 2,2,6,6-tetramethyl-l-oxa-4-aza-2,6-disilacyclohexane (MPSC) hydrochloride, a silicon-containing xenobiotic, in rat, dog, and man
  作者：J. G. Dain、J. Nicoletti

  DOI：10.3109/00498259509046666

  日期：1995.1

  1. The metabolic pathways of Sandoz compound 58-112, 4-[(3-methyoxyphenyl)methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane (MPSC) hydrochloride were evaluated in rat, dog, and man after a single oral dose.2. In rat, dog and man the major route of elimination was renal. In the dog, renal excretion of unchanged MPSC represented a substantial portion of the dose whereas in rat and man MPSC was completely metabolized prior to excretion.3. In rat and man, the major end-product metabolite was 3'-[(hydroxydimethylsilyl)methylamino}methyl]-phenol glucuronide; 4-[(3-hydroxyphenyl)-methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane and 4-[(4-hydroxy-3-methoxyphenyl)methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane and their conjugates were also present. In dog, the major end-product metabolites were the hippurate of 3-methoxybenzoic acid and 3-hydroxybenzoic acid.
• 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.

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