(Z)-1-Methoxy-2-trimethylsilanyl-1-trimethylsilanyloxy-ethene | 35003-74-8

• 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: (Z)-1-Methoxy-2-trimethylsilanyl-1-trimethylsilanyloxy-ethene
• 英文别名: [(Z)-1-methoxy-2-trimethylsilylethenoxy]-trimethylsilane
• CAS: 35003-74-8
• 化学式: C₉H₂₂O₂Si₂
• 分子量: 218.443
• InChiKey: YDKWTYKFQSZAHO-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (Z)-1-Methoxy-2-trimethylsilanyl-1-trimethylsilanyloxy-ethene 、 2-苯基-2-环戊烯-1-酮 生成 (+/-)-methyl 1α,2β-3-oxo-2-phenyl-α-(trimethylsilyl)cyclopentaneacetate
  参考文献：
  名称：

  Billington, David C.; Bladon, Peter; Helps, I. Malcolm, Journal of Chemical Research, Miniprint, 1988, # 10, p. 2601 - 2623

  摘要：

  DOI：
• 作为产物：
  描述：

  (三甲基硅基)乙酸甲酯 、 三甲基氯硅烷 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (Z)-1-Methoxy-2-trimethylsilanyl-1-trimethylsilanyloxy-ethene 、 O-methyl-C,O-bis(trimethylsilyl)ketene acetal
  参考文献：
  名称：

  Quantum Chemical Calculations on the Peterson Olefination with α-Silyl Ester Enolates

  摘要：

  The reaction of stabilized Peterson reagents (alpha-silyl ester enolates) with ketones has been studied theoretically and experimentally. Enolate geometry was studied by trapping experiments and NMR spectroscopy and was found to differ markedly with the nature of the base (LiHMDS vs LDA vs KHMDS), The chelating effect of the lithium counterion was found to be critical for the reaction. For the two ketones studied, the combined weight of experimental and computational data assigns geometrical selectivity to the initial addition transition state, though in general there appears to be a fine balance between three possible choices for the rate-determining step.

  DOI：

  10.1021/jo0262107

文献信息

• BILLINGTON, DAVID C.;BLADON, PETER;HELPS, MALCOLM;PAUSON, PETER L.;THOMSO+, J. CHEM. RES. (S),(1988) N 10, C. 326-327
  作者：BILLINGTON, DAVID C.、BLADON, PETER、HELPS, MALCOLM、PAUSON, PETER L.、THOMSO+

  DOI：——

  日期：——
• Quantum Chemical Calculations on the Peterson Olefination with α-Silyl Ester Enolates
  作者：Malcolm B. Gillies、Janne E. Tønder、David Tanner、Per-Ola Norrby

  DOI：10.1021/jo0262107

  日期：2002.10.1

  The reaction of stabilized Peterson reagents (alpha-silyl ester enolates) with ketones has been studied theoretically and experimentally. Enolate geometry was studied by trapping experiments and NMR spectroscopy and was found to differ markedly with the nature of the base (LiHMDS vs LDA vs KHMDS), The chelating effect of the lithium counterion was found to be critical for the reaction. For the two ketones studied, the combined weight of experimental and computational data assigns geometrical selectivity to the initial addition transition state, though in general there appears to be a fine balance between three possible choices for the rate-determining step.
• Billington, David C.; Bladon, Peter; Helps, I. Malcolm, Journal of Chemical Research, Miniprint, 1988, # 10, p. 2601 - 2623
  作者：Billington, David C.、Bladon, Peter、Helps, I. Malcolm、Pauson, Peter L.、Thomson, William、Willison, Debra

  DOI：——

  日期：——