Formyltrimethylsilane 2,4-dinitrophenylhydrazone | 143370-69-8

• 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: Formyltrimethylsilane 2,4-dinitrophenylhydrazone
• 英文别名: 2,4-dinitro-N-(trimethylsilylmethylideneamino)aniline
• CAS: 143370-69-8
• 化学式: C₁₀H₁₄N₄O₄Si
• 分子量: 282.331
• InChiKey: ZRAILXSSARPHSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1,3-dioxolan-2-yl)trimethylsilane 、 2,4-二硝基苯肼 以 乙醇 为溶剂， 以46%的产率得到Formyltrimethylsilane 2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  Formylsilanes. Chemoenzymic and chemical synthesis of the 2,4-dinitrophenylhydrazones of these apparently air- and water-stable compounds

  摘要：

  Formylsilanes have long been reported to be notoriously unstable compounds. In fact, no formylsilane has been reported that was stable in air or in water nor are there any known hydrates, imines, or hydrazones of formylsilanes. We have found that monoamine oxidase catalyzes the oxidation of (aminomethyl)-tert-butyl-dimethylsilane in aqueous buffer at pH 9 to give, apparently, either formyl-tert-butyldimethylsilane or the corresponding hydrate, which is isolated as the 2,4-dinitrophenylhydrazone. The chemical synthesis of this same compound and the corresponding formyltrimethylsilane was carried out in low yields by a standard route to acylsilanes but in good yields by a new route involving conversion of (1,3-dioxolan-2-yl)tri-n-butylstannane to the corresponding silanes followed by acid hydrolysis. Although the formylsilane could not be isolated, it or its hydrate apparently is stable enough in water to survive incubation for several hours prior to the 2,4-dinitrophenylhydrazine trapping reaction.

  DOI：

  10.1021/jo00050a046

文献信息

• A Mild and General Approach to the Preparation and Trapping of Highly Reactive Formylsilanes
  作者：Alan R. Katritzky、Zhijun Yang、Qingmei Hong

  DOI：10.1021/jo00096a070

  日期：1994.8
• Formylsilanes. Chemoenzymic and chemical synthesis of the 2,4-dinitrophenylhydrazones of these apparently air- and water-stable compounds
  作者：Richard B. Silverman、Xingliang Lu、Gregory M. Banik

  DOI：10.1021/jo00050a046

  日期：1992.11

  Formylsilanes have long been reported to be notoriously unstable compounds. In fact, no formylsilane has been reported that was stable in air or in water nor are there any known hydrates, imines, or hydrazones of formylsilanes. We have found that monoamine oxidase catalyzes the oxidation of (aminomethyl)-tert-butyl-dimethylsilane in aqueous buffer at pH 9 to give, apparently, either formyl-tert-butyldimethylsilane or the corresponding hydrate, which is isolated as the 2,4-dinitrophenylhydrazone. The chemical synthesis of this same compound and the corresponding formyltrimethylsilane was carried out in low yields by a standard route to acylsilanes but in good yields by a new route involving conversion of (1,3-dioxolan-2-yl)tri-n-butylstannane to the corresponding silanes followed by acid hydrolysis. Although the formylsilane could not be isolated, it or its hydrate apparently is stable enough in water to survive incubation for several hours prior to the 2,4-dinitrophenylhydrazine trapping reaction.