乙氧基甲基(三甲基)硅烷 | 17348-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙氧基甲基(三甲基)硅烷
• 中文别名: (乙氧甲基)三甲基硅烷
• 英文名称: (trimethylsilyl)methyl ethyl ether
• 英文别名: (Ethoxymethyl)(trimethyl)silane；ethoxymethyl(trimethyl)silane
• CAS: 17348-58-2
• 化学式: C₆H₁₆OSi
• 分子量: 132.278
• InChiKey: DGNQBKNQTOMWAO-UHFFFAOYSA-N

物化性质

• 沸点：
  102.3-102.9 °C
• 密度：
  0.7538 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9,10-二氰基蒽 、 乙氧基甲基(三甲基)硅烷 以 乙腈 为溶剂， 反应 10.0h， 以39%的产率得到10-(ethoxymethyl)-9H-anthracene-9,10-dicarbonitrile
  参考文献：
  名称：

  Photoadditions of ethers, thioethers, and amines to 9,10-dicyanoanthracene by electron transfer pathways

  摘要：

  DOI：

  10.1021/jo00258a007
• 作为产物：
  描述：

  sodium ethanolate 、 氯甲基三甲基硅烷 以 not given 为溶剂， 以70%的产率得到乙氧基甲基(三甲基)硅烷
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 4, page 14 - 18

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-phenyl-1-pyrrolinium perchlorate 在 乙氧基甲基(三甲基)硅烷 作用下， 以 乙腈 为溶剂， 生成 2-(ethoxymethyl)-2-phenylpyrrolidine 、 2,2'-diphenyl-2,2'-bipyrrolidine
  参考文献：
  名称：

  通过光化学电子转移诱导RXCH2SiMe3体系脱甲硅烷基产生杂原子取代自由基的新方法

  摘要：

  练习题 d'addition photochimique d'ethers ou suluss d'alkyl et trimethylsilymethyl avec le phenyl-2 pyrroline-1ium et des photoadditions intramoleculaires d'ω-trimethylsilmethoxyalkyl-1, -2 ou -4 quinoleineiniums

  DOI：

  10.1021/ja00334a072

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 4, page 14 - 18
  作者：

  DOI：——

  日期：——
• Photoaddition reactions of acenaphthylenedione with .alpha.-silyl n-electron donors via triplet single electron transfer desilylation and triplet hydrogen atom abstraction pathways
  作者：Ung Chan Yoon、Yong Chul Kim、Jeong Ja Choi、Dong Uk Kim、Patrick S. Mariano、In Seop Cho、Yoon Tag Jeon

  DOI：10.1021/jo00031a020

  日期：1992.2

  Studies have been conducted to explore single electron transfer (SET) induced photoaddition reactions of acenaphthylenedione (ACND) with the n-electron donors Et2NCH2SiMe3, n-PrSCH2SiMe3, EtOCH2SiMe3, EtCO2CH2N(CH2Ph)CH2SiMe3, and EtCO2CH2N(CH2Ph)CH3. Photoaddition of alpha-silyl amine Et2NCH2SiMe3 to ACND occurs in CH3OH and CH3CN to produce 2-hydroxy-2-[(diethylamino)methyl]acenaphthylen-1-one. In contrast, photoaddition of n-PrSCH2SiMe3 to ACND generates two photoadducts, 2-hydroxy-2-[(n-propylthio)methyl]acenaphthylen-1-one and 2-hydroxy-2-[(n-propylthio)(trimethylsilyl)methyl]acenaphthylen-1-one, along with a ACND photoreduction dimer. Photoaddition of EtOCH2SiMe3 to ACND produces two diastereomers of 2-hydroxy-2-[ethoxy(trimethylsilyl)methyl]acenaphthylen-1-one along with the reduction dimer. The formation of all photoproducts in these photoreactions is quenched by oxygen, indicating that the triplet of ACND is the reactive excited state. Based on a consideration of the oxidation potentials of the alpha-silyl n-electron donors, and the nature of photoproducts, mechanisms for these photoadditions involving triplet SET-desilylation and triplet H atom abstraction pathways are proposed. Photoaddition of EtCO2CH2N(CH2Ph)CH2SiMe3 to ACND provides two major products, 2-hydroxy-2-[[N-benzyl-N-(carbethoxymethyl)amino]methyl]acenaphthylen-1-one and 2-hydroxy-2-[[N-benzyl-N-[(trimethylsilyl)methyl]amino]carbethoxymethyl]acenaphthylen-1-one along with several minor products. The formation of the major products via sequential SET-deprotonation pathways shows that the electron-withdrawing carbethoxy substituent serves to control the regioselectivity for deprotonation of the amine radical cation intermediate. Results obtained from the study of the photoaddition of the non-silicon-containing amino ester, EtCO2CH2N(CH2Ph)CH3, also demonstrate the effect of electron-withdrawing carbethoxy substituent on amine radical cation deprotonation regiochemistry.
• Roedel, Journal of the American Chemical Society, 1949, vol. 71, p. 271
  作者：Roedel

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 3, page 11 - 14
  作者：

  DOI：——

  日期：——
• Synthesis of Alkoxymethyltrimethylsilanes
  作者：John L. Speier

  DOI：10.1021/ja01192a049

  日期：1948.12