O-methyl-C,O-bis(trimethylsilyl)ketene acetal | 35003-73-7

• 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: O-methyl-C,O-bis(trimethylsilyl)ketene acetal
• 英文别名: (E)-(trimethylsilyl)ketene trimethylsilyl methyl acetal；[(E)-1-methoxy-2-trimethylsilylethenoxy]-trimethylsilane
• CAS: 35003-73-7
• 化学式: C₉H₂₂O₂Si₂
• 分子量: 218.443
• InChiKey: YDKWTYKFQSZAHO-CMDGGOBGSA-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：

  O-methyl-C,O-bis(trimethylsilyl)ketene acetal 以92%的产率得到
  参考文献：
  名称：

  SERGEEV V. N.; SHIPOV A. G.; ZAJTSEVA G. S.; BAUKOV YU. I., ZH. OBSHCH. XIMII, 1979, HO 12, 2753-2762

  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 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以99%的产率得到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

• Stereocontrolled synthesis of α,β-unsaturated carboxylic esters from O-methyl-C,O-bis(trimethylsilyl)ketene acetal and aliphatic aldehydes
  作者：Isamu Matsuda、Yusuke lzumi

  DOI：10.1016/s0040-4039(01)90445-9

  日期：1981.1

  (R*,S*) Selective aldol type reaction of O-methyl-C,O-bis(trimethylsilyl)ketene acetal () with aldehydes and stereoselective formation of α,β-unsaturated carboxylic esters are attained by the combination of Z- and Lewis acids.

  （R *，S *）O-甲基-C，O-双（三甲基甲硅烷基）乙烯酮缩醛（）与醛的选择性羟醛型反应，通过Z-和C-的结合可实现立体选择性地形成α，β-不饱和羧酸酯路易斯酸。
• Zaitseva, G. S.; Livantsova, L. I.; Novikova, O. P., Journal of general chemistry of the USSR, 1992, vol. 62, # 8, p. 1519 - 1524
  作者：Zaitseva, G. S.、Livantsova, L. I.、Novikova, O. P.、Baukov, Yu. I.、Petrosyan, V. S.

  DOI：——

  日期：——
• MATSUDA ISAMU; MURATA SHIZUAKI; IZUMI YUSUKE, J. ORG. CHEM. 1980, 45, NO 2, 237-240
  作者：MATSUDA ISAMU、 MURATA SHIZUAKI、 IZUMI YUSUKE

  DOI：——

  日期：——
• MATSUDA ISAMU; IZUMI YUSUKE, TETRAHEDRON LETT., 1981, 22, NO 19, 1805-1808
  作者：MATSUDA ISAMU、 IZUMI YUSUKE

  DOI：——

  日期：——
• EMDE, H.;SIMCHEN, G., LIEBIGS ANN. CHEM., 1983, N 5, 816-834
  作者：EMDE, H.、SIMCHEN, G.

  DOI：——

  日期：——