(trimethylsilyl)sodium | 33019-95-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: (trimethylsilyl)sodium
• CAS: 33019-95-3
• 化学式: C₃H₉NaSi
• 分子量: 96.1797
• InChiKey: BFHAFMNXQXTMQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (trimethylsilyl)sodium 以50%的产率得到
  参考文献：
  名称：

  CORRIU R. J. P.; GUERIN C., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 4, 168-169

  摘要：

  DOI：

文献信息

• Gas-Phase Diastereoselectivity of Secondary 5-Substituted (X)-Adamant-2-yl (X = F, Si(CH₃)₃) Cations
  作者：Caterina Fraschetti、Francesca R. Novara、Antonello Filippi、Neil A. Trout、William Adcock、Ted S. Sorensen、Maurizio Speranza

  DOI：10.1021/jo0702140

  日期：2007.5.1

  Secondary 5-X-adamant-2-yl cations I-X (X = F, Si(CH3)(3)) have been generated in the gas phase (total pressure = 760 Torr) from protonation-induced defluorination of epimeric 2-F-5-X-adamantanes 1(X) and their kinetic diastereoselectivity toward (CH3OH)-O-18 investigated in the 40-160 degrees C range. The experimental results indicate that the facial selectivity of I-X is insensitive to the composition of the starting 1(X) epimers as well as to the presence and the concentration of a powerful base (N(C2H5)(3)). This kinetic picture, supported by B3LYP/6-31G* calculations, is consistent with a single stable pyramidalized structure for I-X, that is, (Z)-5-F-adamant-2-yl (I-F(Z)) and (E)-5-Si(CH3)(3)-adamant-2-yl cations (I-Si(E)). The temperature dependence of the I-X diastereoselectivity lends support to the intermediacy of noncovalent adducts [(IXCH3OH)-C-.-O-18], characterized by a specific C2-(H+...O18)(H)CH3 hydrogen bonding interaction. Their conversion to the covalently bonded O-methylated (Z)- (IIXZ) and (E)-5-X-adamantan-2-ols (IIXE; X = F, Si(CH3)(3)) is governed by activation parameters, whose magnitude depends on the specific I-X face accommodating (CH3OH)-O-18. The gas-phase diastereoselectivity of I-X toward (CH3OH)-O-18 is compared to that exhibited in related gas-phase and solution processes. The emerging picture indicates that the factors determining the diastereoselectivity of I-X toward simple nucleophiles in the gaseous and condensed media are completely different.
• PIRRUNG M. C.; WEBSTER N. J. G., TETRAHEDRON LETT., 27,(1986) N 34, 3983-3986
  作者：PIRRUNG M. C.、 WEBSTER N. J. G.

  DOI：——

  日期：——
• CORRIU R. J. P.; GUERIN C., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 4, 168-169
  作者：CORRIU R. J. P.、 GUERIN C.

  DOI：——

  日期：——