(1,3-dioxolan-2-yl)-tert-butyldimethylsilane | 143370-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (1,3-dioxolan-2-yl)-tert-butyldimethylsilane
• 英文别名: Tert-butyl-(1,3-dioxolan-2-yl)-dimethylsilane
• CAS: 143370-62-1
• 化学式: C₉H₂₀O₂Si
• 分子量: 188.342
• InChiKey: VBXOVHBBADCQKG-UHFFFAOYSA-N

物化性质

• 沸点：
  196.1±25.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,3-dioxolan-2-yl)-tert-butyldimethylsilane 、 2,4-二硝基苯肼 以 乙醇 为溶剂， 以70%的产率得到formyl-tert-butyldimethylsilane 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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 正丁基锂 、 tetrabutylammonium tetrafluoroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 20.8h， 生成 (1,3-dioxolan-2-yl)-tert-butyldimethylsilane
  参考文献：
  名称：

  甲硅烷基缩醛的简便电化学合成：甲酰基硅烷的空气稳定前体

  摘要：

  本研究描述了一种简便的电化学合成甲硅烷基乙缩醛（甲酰基硅烷的合成等效物）的方法。使用未分裂的电池和铂和不锈钢电极，2-甲硅烷基-1,3-二噻烷与一元醇和二醇在乙腈中的恒流电解产生各种甲硅烷醇缩醛。甲硅烷基乙缩醛很容易转化为相应的甲酰基硅烷。这种不含汞试剂的方法将是传统甲酰基硅烷合成的一种更环保的替代方法。

  DOI：

  10.1016/j.tetlet.2022.154026

文献信息

• 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.
• Facile electrochemical synthesis of silyl acetals: An air-stable precursor to formylsilane
  作者：Masahiro Noji、Sho Ishimaru、Haruki Obata、Ayano Kumaki、Taichi Seki、Satoshi Hayashi、Toshikatsu Takanami

  DOI：10.1016/j.tetlet.2022.154026

  日期：2022.8

  A facile electrochemical synthesis of silyl acetal, a synthetic equivalent of formylsilane, was described in this study. Using undivided cells and platinum and stainless-steel electrodes, the constant current electrolysis of 2-silyl-1,3‑dithiane with monoalcohol and diol in acetonitrile yielded various silyl acetals. The silyl acetal was readily converted to the corresponding formylsilane. This method

  本研究描述了一种简便的电化学合成甲硅烷基乙缩醛（甲酰基硅烷的合成等效物）的方法。使用未分裂的电池和铂和不锈钢电极，2-甲硅烷基-1,3-二噻烷与一元醇和二醇在乙腈中的恒流电解产生各种甲硅烷醇缩醛。甲硅烷基乙缩醛很容易转化为相应的甲酰基硅烷。这种不含汞试剂的方法将是传统甲酰基硅烷合成的一种更环保的替代方法。