<2-Triaethylsilyl-vinyl>-aethyl-aether | 125555-84-2

• 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-Triaethylsilyl-vinyl>-aethyl-aether
• 英文别名: (2-ethoxy-vinyl)-triethyl-silane；1-Aethoxy-2-triaethylsilyl-aethen；(2-Aethoxy-vinyl)-triaethyl-silan；[(E)-2-ethoxyethenyl]-triethylsilane
• CAS: 125555-84-2
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: RFKQEVVHHBUZOX-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-溴-2-乙氧基乙烯 、 三乙基氯硅烷 在 正丁基锂 作用下， 生成 <2-Triaethylsilyl-vinyl>-aethyl-aether
  参考文献：
  名称：

  2-Ethoxyvinyllithiums and diethoxyvinyllithiums : what makes them stable or fragile?

  摘要：

  The elusive (E)-2-ethoxyvinyllithium can be readily generated in tetrahydrofuran at -75 degrees C from (E)-1-bromo-2-ethoxyethylene by halogen/metal exchange and subsequently trapped with electrophiles. Alkylation opens a convenient entry to (E)-configurated enethers. (E)-2-Ethoxyvinyllithium decomposes rapidly at -50 degrees C whereas its (Z)-isomer, which lacks the possibility to eliminate lithium ethoxide in a favorable anti-periplanar process, is stable under the same conditions. (E)-1,2-Diethoxyvinyllithium even sustains reflux temperatures (approximately 75 degrees C). 2,2-Diethoxyvinyllithium and (Z)-1,2-diethoxyvinyllithium can be conserved at 0 degrees C although this time loss of alcoholate can occur in the anti-mode. Obviously it matters whether the energy-rich ethoxyacetylene is formed as the elimination product or simple acetylene, as in the case of (E)-2-ethoxyvinyllithium. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01075-7

文献信息

• KUZMINA, N. A.;ILINSKAYA, L. V.;:, SAVOSKINA I. V.;GALUSTYAN, G. G.;CHUKO+, METALLOORGAN. XIMIYA, 2,(1989) N, S. 388-391
  作者：KUZMINA, N. A.、ILINSKAYA, L. V.、:, SAVOSKINA I. V.、GALUSTYAN, G. G.、CHUKO+

  DOI：——

  日期：——
• Freidlina et al., Doklady Akademii Nauk SSSR, 1959, vol. 127, p. 352,355
  作者：Freidlina et al.

  DOI：——

  日期：——
• 2-Ethoxyvinyllithiums and diethoxyvinyllithiums : what makes them stable or fragile?
  作者：Manfred Schlosser、Heng-xu Wei

  DOI：10.1016/s0040-4020(96)01075-7

  日期：1997.2

  The elusive (E)-2-ethoxyvinyllithium can be readily generated in tetrahydrofuran at -75 degrees C from (E)-1-bromo-2-ethoxyethylene by halogen/metal exchange and subsequently trapped with electrophiles. Alkylation opens a convenient entry to (E)-configurated enethers. (E)-2-Ethoxyvinyllithium decomposes rapidly at -50 degrees C whereas its (Z)-isomer, which lacks the possibility to eliminate lithium ethoxide in a favorable anti-periplanar process, is stable under the same conditions. (E)-1,2-Diethoxyvinyllithium even sustains reflux temperatures (approximately 75 degrees C). 2,2-Diethoxyvinyllithium and (Z)-1,2-diethoxyvinyllithium can be conserved at 0 degrees C although this time loss of alcoholate can occur in the anti-mode. Obviously it matters whether the energy-rich ethoxyacetylene is formed as the elimination product or simple acetylene, as in the case of (E)-2-ethoxyvinyllithium. (C) 1997, Elsevier Science Ltd.