2-(2,5-dimethoxyphenyl)-2-(trimethylsilyloxy)acetonitrile | 141367-35-3

• 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-(2,5-dimethoxyphenyl)-2-(trimethylsilyloxy)acetonitrile
• 英文别名: 2-(2,5-Dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile
• CAS: 141367-35-3
• 化学式: C₁₃H₁₉NO₃Si
• 分子量: 265.384
• InChiKey: XVOXXBOEXBDGDM-UHFFFAOYSA-N

物化性质

• 沸点：
  344.5±42.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-(2,5-dimethoxyphenyl)-2-(trimethylsilyloxy)acetonitrile 在 盐酸 、 lithium aluminium tetrahydride 作用下， 生成 alpha-(氨基甲基)-2,5-二甲氧基苄醇盐酸盐
  参考文献：
  名称：

  Asymmetric synthesis of both enantiomers of 2-(dimethylamino)-1-[3-methoxy-2-(1-methylethoxy)phenyl]ethanol

  摘要：

  Both enantiomers of 2-(dimethylamino)-1-[3-methoxy-2-(1- methylethoxy)phenyl]ethanol were synthetized by a stereoselective route and evaluated in vitro for their uroselectivity in Comparison with other alpha-adrenoceptor agonists. The most potent enantiomer was structurally characterized by X-ray crystallographic analysis.

  DOI：

  10.1016/s0223-5234(97)82773-0
• 作为产物：
  描述：

  三甲基氰硅烷 、 2,5-二甲氧基苯甲醛 在 C₁₆H₂₃N₃Sn 作用下， 以 neat (no solvent) 为溶剂， 以96%的产率得到2-(2,5-dimethoxyphenyl)-2-(trimethylsilyloxy)acetonitrile
  参考文献：
  名称：

  亚锡基氰化物及其作为氰基硅烷化催化剂的用途

  摘要：

  两条路线可以提供第一亚锡氰化物[(L)SnCN] ( 5 )；亚锡酰胺 [( i -Bu ) 2 ATISnN(SiMe 3 ) 2 ] ( 3 ) 或亚锡基吡咯烷 [( i -Bu ) 2 ATISn(NC 4 H 4 )] ( 4 ) 使用过量的三甲基甲硅烷基的取代反应氰化物（L = 氨基托酰亚胺 (ATI)）。使用 0.1–2.0 mol% 的化合物5，在 rt-50 °C 下，在 0.33-2.0 小时内实现了多种脂肪族和芳香族醛的催化氰基硅烷化。这种催化反应的机制通过结构特征中间体的分离得到证实。

  DOI：

  10.1039/d2dt02721f

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。
• A cationic aluminium complex: an efficient mononuclear main-group catalyst for the cyanosilylation of carbonyl compounds
  作者：Mahendra Kumar Sharma、Soumen Sinhababu、Goutam Mukherjee、Gopalan Rajaraman、Selvarajan Nagendran

  DOI：10.1039/c7dt01760j

  日期：——

  A structurally characterized cationic aluminium complex [(AT)Al(DMAP)]+[OTf]- (3) stabilized through less bulky aminotroponate (AT) ligand is reported (DMAP = 4-(dimethylamino)pyridine). It works as an excellent mononuclear main-group catalyst (1 to 2 mol%) for the cyanosilylation of a variety of aldehydes and ketones by consuming just 5 to 30 min at room temperature.

  据报道，结构上具有特征性的阳离子铝络合物[（AT）Al（DMAP）] + [OTf]-（3）通过较小体积的氨基肌酸（AT）配体稳定化（DMAP = 4-（二甲基氨基）吡啶）。它在室温下仅需5至30分钟即可用作多种醛和酮的氰基甲硅烷基化反应的极好单核主族催化剂（1至2 mol％）。
• 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。
• 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.
• Perez; Rosell; Mauleon, Il Farmaco, 1991, vol. 46, # 10, p. 1155 - 1166
  作者：Perez、Rosell、Mauleon、Carganico

  DOI：——

  日期：——