2-(2,3-Dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile | 521970-04-7

• 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-(2,3-Dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile
• CAS: 521970-04-7
• 化学式: C₁₃H₁₉NO₃Si
• mdl: MFCD17500741
• 分子量: 265.384
• InChiKey: IYBWZILXAHLRPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-Dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2,3-二甲氧基苯基)-2-羟基乙腈
  参考文献：
  名称：

  酶法制备旋光氰醇乙酸酯

  摘要：

  通过在酯存在下进行酶促外消旋乙酸酯的酶水解，可以制备出具有良好化学性质且通常具有高光学收率的一系列结构广泛变化的氰氨醇乙酸酯（1）–（47），可用于许多合成应用假单胞菌（Pseudomonas sp）的水解酶。

  DOI：

  10.1039/c39890001391
• 作为产物：
  描述：

  三甲基氰硅烷 、 2,3-二甲氧基苯甲醛 在 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 65.0h， 生成 2-(2,3-Dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile
  参考文献：
  名称：

  恶唑烷二酮治疗大鼠的葡萄糖耐量提高。

  摘要：

  5-（2-氯-6-甲氧基苯基）恶唑烷-2,4-二酮（49）是选自一系列5-取代的恶唑烷二酮类中最有效的药物，已发现这些物质可改善先前禁食的大鼠的葡萄糖耐量和增强能力响应葡萄糖激发的胰岛素释放。这些化合物的独特之处在于不会产生低于正常空腹血糖水平的低血糖。研究了苯环2-6位的取代基效应。发现替代的最佳位置是2-，5-和6-位。恶唑烷二酮环的变化通常导致活性降低。详细介绍了该系列的合成和构效关系。

  DOI：

  10.1021/jm00155a030

文献信息

• Improved glucose tolerance in rats treated with oxazolidinediones
  作者：Rodney C. Schnur、Malcolm Morville

  DOI：10.1021/jm00155a030

  日期：1986.5

  5-(2-Chloro-6-methoxyphenyl)oxazolidine-2,4-dione (49) is the most potent agent selected from a series of 5-substituted oxazolidinediones that were found to cause improvements in glucose tolerance in previously fasted rats and potentiation of insulin release in response to a glucose challenge. These compounds were unique in not producing hypoglycemia below the normal fasting glycemia levels. Substituent

  5-（2-氯-6-甲氧基苯基）恶唑烷-2,4-二酮（49）是选自一系列5-取代的恶唑烷二酮类中最有效的药物，已发现这些物质可改善先前禁食的大鼠的葡萄糖耐量和增强能力响应葡萄糖激发的胰岛素释放。这些化合物的独特之处在于不会产生低于正常空腹血糖水平的低血糖。研究了苯环2-6位的取代基效应。发现替代的最佳位置是2-，5-和6-位。恶唑烷二酮环的变化通常导致活性降低。详细介绍了该系列的合成和构效关系。
• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
• Enzymatic preparation of optically active cyanohydrin acetates
  作者：Andreas van Almsick、Joachim Buddrus、Petra Hönicke-Schmidt、Kurt Laumen、Manfred P. Schneider

  DOI：10.1039/c39890001391

  日期：——

  A series of cyanohydrin acetates (1)–(47) of widely varying structures, potential chiral building blocks for numerous synthetic applications, has been prepared in good chemical and often high optical yields by enzymatic hydrolysis of their racemic acetates in the presence of an ester hydrolase from Pseudomonas sp.

  通过在酯存在下进行酶促外消旋乙酸酯的酶水解，可以制备出具有良好化学性质且通常具有高光学收率的一系列结构广泛变化的氰氨醇乙酸酯（1）–（47），可用于许多合成应用假单胞菌（Pseudomonas sp）的水解酶。
• Synthesis and Quantitative Structure−Activity Relationships of <i>N</i>-(1-Benzylpiperidin-4-yl)phenylacetamides and Related Analogues as Potent and Selective σ₁ Receptor Ligands
  作者：Yunsheng Huang、Philip S. Hammond、Brian R Whirrett、Ross J. Kuhner、Li Wu、Steven R. Childers、Robert H. Mach

  DOI：10.1021/jm980032l

  日期：1998.6.1

  A series of N-(1-benzylpiperidin-4-yl)pherlylacetamide derivatives was synthesized and evaluated for affinity at or and oz receptors. Most of these compounds showed a high affinity for sigma(1) receptors and a low to moderate affinity for sigma(2) receptors. The unsubstituted compound N-(1-benzylpiperidin-4-yl)phenylacetamide, 1, displayed a high affinity and selectivity for sigma(1) receptors (K-i) values of 3.90 nM for sigma(1) receptors and 240 nM for sigma(2) receptors. The influence of substitutions on the phenylacetamide aromatic ring on binding at both the sigma(1) and sigma(2) receptor has been examined through Hansch-type quantitative structure-activity relationship (QSAR) studies. In general, all 3-substituted compounds, except for the OH group, had a higher affinity for both sigma(1) and sigma(2) receptors when compared with the corresponding 2- and 4-substituted analogues. The selectivity for sigma(1) receptors displayed a trend of 3 > 2 approximate to 4 for Cl, Pr, F, NO2, and OMe substituted analogues. Halogen substitution on the aromatic ring generally increased the affinity for sigma(2) receptors while maintaining a similar affinity for sigma(1) receptors. Substitution with electron-donating groups, such as OH, OMe, or NH2, resulted in weak or negligible affinity for sigma(2) receptors and a moderate affinity for sigma(1) receptors. The 2-fluoro-substituted analogue, 11, exhibited the highest selectivity for sigma(1) receptors among all compounds tested, with a K-i value of 3.56 nM for sigma(1) receptors and 667 nM for sigma(2) receptors. Compounds 1, 5, 9, 11, and 20 had no affinity for dopamine D-2 (IC50 > 10 000 nM) and D-3 (IC50 > 10 000 nM) receptors. The nanomolar binding affinity and high selectivity for sigma(1) receptors suggest that these compounds may be developed as potential radiotracers for positron emission tomography or single photon emission computerized tomography imaging studies.