2-<(Trimethylsilyl)oxy>ethanenitrile | 40326-15-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-<(Trimethylsilyl)oxy>ethanenitrile
• 英文别名: Trimethylsilyloxyacetonitril；2-((Trimethylsilyl)oxy)acetonitrile；2-trimethylsilyloxyacetonitrile
• CAS: 40326-15-6
• 化学式: C₅H₁₁NOSi
• 分子量: 129.234
• InChiKey: SVVZXVWJFYDKNR-UHFFFAOYSA-N

物化性质

• 沸点：
  124.6±23.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(Trimethylsilyl)oxy>ethanenitrile 在 四甲基乙二胺 、 lithium diethylamide 、 lithium diisopropyl amide 作用下， 生成 2,3-Bis(trimethylsilyl)-2-<(trimethylsilyl)oxy>propanenitrile
  参考文献：
  名称：

  Metalation-alkylation of O-trimethylsilyl formyltrimethylsilane cyanohydrin in the synthesis of oxazoles

  摘要：

  DOI：

  10.1021/jo00051a064
• 作为产物：
  描述：

  三聚甲醛 、 三甲基氰硅烷 在 zinc(II) iodide 作用下， 反应 48.0h， 以90%的产率得到2-<(Trimethylsilyl)oxy>ethanenitrile
  参考文献：
  名称：

  The metalation-silylation of O-trimethylsilyl aldehyde cyanohydrins

  摘要：

  The metalation-trimethylsilyation of O-trimethylsilyl (saturated) aldehyde cyanohydrins was achieved by in situ treatment with LDA and trimethylchlorosilane at -78-degrees-C. C-Silyl products (O-trimethylsilyl acylsilane cyanohydrins) generally predominated, but N-silyl derivatives (ketenimines) were found in some instances. LDA could be added across the C = N bond of the latter. The metalation-trimethylsilylation of O-trimethylsilyl benzaldehyde cyanohydrin could only be effected if 2 equiv of trimethylchlorosilane were employed per equivalent of cyanohydrin anion.

  DOI：

  10.1021/jo00030a030

文献信息

• Cyanosilylation of aldehydes and ketones. A convenient route to cyanohydrin derivatives
  作者：D. A. Evans、L. K. Truesdale、G. L. Carroll

  DOI：10.1039/c39730000055

  日期：——

  A wide variety of aldehydes and ketones reacts with trimethylsilyl cyanide under both thermal and catalytic conditions to give α-silyloxy nitriles which may be useful intermediates and protective groups in organic synthesis.

  各种各样的醛和酮在热和催化条件下与三甲基甲硅烷基氰化物反应，生成α-甲硅烷氧基腈，它们可能是有机合成中有用的中间体和保护基。
• A General Synthesis of 3,5-Dihalo-2<i>H</i>-1,4-oxazin-2-ones from Cyanohydrins
  作者：Lieven Meerpoel、Georges Hoornaert

  DOI：10.1055/s-1990-27049

  日期：——

  In a novel approach starting from O-trimethylsilyl protected or unprotected cyanohydrins and oxalyl chloride or bromide, a series of unknown 6-substituted 3,5-dihalo-2H-1,4-oxazin-2-ones were prepared. The method was shown to be efficient for various types of cyanohydrins; however cyclization was not obtained with cyanohydrins containing bulky substituents, electron-rich aryl or heteroaryl groups. A mechanism is proposed.

  从O-三甲基硅烷保护或未保护的氰醇以及草酰氯或溴开始，采用一种新颖的方法合成了一系列未知的6-取代-3,5-二卤代-2H-1,4-恶嗪-2-酮。该方法对各种类型的氰醇都显示出高效性；然而，对于含有大体积取代基、富电子芳基或杂芳基的氰醇，未能实现环化反应。提出了一个可能的反应机理。
• Synthesis of 3,5-dihalogeno-2H-1,4-oxazin-2-ones from cyanohydrines
  作者：L. Meerpoel、G. Hoornaert

  DOI：10.1016/s0040-4039(00)99196-2

  日期：——

  The title compounds were obtained on treatment of cyanohydrines of aliphatic and aryl aldehydes with oxalyl chloride or bromide in chlorobenzene at 90°C. Evidence for their structure is given by their spectroscopic data and by the Diels Alder reaction of a and g with acetylenic dienophiles to yield substituted pyridines. Cycloaddition was also observed with ethene.

  在90℃下用草酰氯或溴化物在氯苯中处理脂族和芳基醛的氰醇，得到标题化合物。其结构的证据由其光谱数据以及a和g与炔属双亲二烯体的狄尔斯-阿尔德反应（Diels Alder reaction）给出，以产生取代的吡啶。还观察到了与乙烯的环加成反应。
• Stannylene cyanide and its use as a cyanosilylation catalyst
  作者：Vivek Kumar Singh、Prakash Chandra Joshi、Hemant Kumar、Rahul Kumar Siwatch、Chandan Kumar Jha、Selvarajan Nagendran

  DOI：10.1039/d2dt02721f

  日期：——

  Two routes can offer the first stannylene cyanide [(L)SnCN] (5); the substitution reaction of either stannylene amide [(i-Bu)2ATISnN(SiMe3)2] (3) or stannylene pyrrolide [(i-Bu)2ATISn(NC4H4)] (4) using an excess of trimethylsilyl cyanide (L = aminotroponiminate (ATI)). Using 0.1–2.0 mol% of compound 5, catalytic cyanosilylation of a variety of aliphatic and aromatic aldehydes was achieved at rt−50 °C

  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。
• SCHNUR, RODNEY C.
  作者：SCHNUR, RODNEY C.

  DOI：——

  日期：——