2-butanedioic anhydride | 141527-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-butanedioic anhydride
• 英文别名: 2-(tris(trimethylsilyl)silyl)butanedioic anhydride；3-Tris(trimethylsilyl)silyloxolane-2,5-dione；3-tris(trimethylsilyl)silyloxolane-2,5-dione
• CAS: 141527-51-7
• 化学式: C₁₃H₃₀O₃Si₄
• 分子量: 346.721
• InChiKey: CENOXZUOGUSHBR-UHFFFAOYSA-N

物化性质

• 沸点：
  344.8±52.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  马来酸酐 、 三(三甲基硅基)硅烷 反应 20.0h， 以87%的产率得到2-butanedioic anhydride
  参考文献：
  名称：

  Modification and chemical transformation of Si(111) surface

  摘要：

  Modification of hydrogen-terminated Si(111) surfaces by hydrosilylation of activated alkenes and further chemical transformation of the modified surfaces is reported. A Si(111)-H surface was reacted with activated alkenes such as acrylate esters, acrylonitrile, and maleic anhydride under mild conditions to give modified surfaces with terminal functional groups. A modified surface with a terminal ester group was reduced by LiAlH4 to give a hydroxy-terminated surface, and the hydroxy-terminated surface was transformed to a bromo-terminated surface. XPS analysis revealed that the brominated surface ( Si(111)-CH2CH2CH2Br) had 32% coverage with the 3-bromopropyl group. Ester and amide formation reactions were carried out on hydroxy- and carboxy-terminated Si surfaces by reaction with tert-butoxycarbonyl glycine, glycine tort-butyl ester, 2,2,2-trifluoroethanol and 4-trifluoromethylbenzyl alcohol in the presence of carbodiimide. XPS characterization indicated that the esters and amide were successfully formed with coverage ranging from 16% to 58%. Coverage ratios of octadecyl ester modified surfaces were also estimated by combination of surface reduction and gas chromatography analysis to be 25-35%. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.09.048

文献信息

• Tris(trimethylsilyl)silane: an efficient hydrosilylating agent of alkenes and alkynes
  作者：B. Kopping、C. Chatgilialoglu、M. Zehnder、B. Giese

  DOI：10.1021/jo00040a048

  日期：1992.7

  Tris(trimethylsilyl)silane adds across the double bond of a variety of mono-, di-, and trisubstituted olefins under free-radical conditions in good yields. The reaction, which proceeds via a free-radical chain mechanism, is highly regioselective (anti-Markovnikov). Addition to prochiral olefins bearing an ester group is highly stereoselective. The factors that control the stereochemistry have been discussed terms of preferred conformations of the intermediate carbon-centered radicals and are thought to be of steric origin.
• Modification and chemical transformation of Si(111) surface
  作者：Yang Liu、Shoko Yamazaki、Suguru Izuhara

  DOI：10.1016/j.jorganchem.2006.09.048

  日期：2006.12

  Modification of hydrogen-terminated Si(111) surfaces by hydrosilylation of activated alkenes and further chemical transformation of the modified surfaces is reported. A Si(111)-H surface was reacted with activated alkenes such as acrylate esters, acrylonitrile, and maleic anhydride under mild conditions to give modified surfaces with terminal functional groups. A modified surface with a terminal ester group was reduced by LiAlH4 to give a hydroxy-terminated surface, and the hydroxy-terminated surface was transformed to a bromo-terminated surface. XPS analysis revealed that the brominated surface ( Si(111)-CH2CH2CH2Br) had 32% coverage with the 3-bromopropyl group. Ester and amide formation reactions were carried out on hydroxy- and carboxy-terminated Si surfaces by reaction with tert-butoxycarbonyl glycine, glycine tort-butyl ester, 2,2,2-trifluoroethanol and 4-trifluoromethylbenzyl alcohol in the presence of carbodiimide. XPS characterization indicated that the esters and amide were successfully formed with coverage ranging from 16% to 58%. Coverage ratios of octadecyl ester modified surfaces were also estimated by combination of surface reduction and gas chromatography analysis to be 25-35%. (c) 2006 Elsevier B.V. All rights reserved.