<4-Methyl-phenoxy>-triphenyl-silan | 17336-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <4-Methyl-phenoxy>-triphenyl-silan
• 英文别名: Triphenyl-p-methylphenoxysilan；(4-Methylphenoxy)-triphenylsilane
• CAS: 17336-24-2
• 化学式: C₂₅H₂₂OSi
• 分子量: 366.535
• InChiKey: TWWXTZDNNBIIAG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  对甲酚 、 乙氧基三苯基硅烷 在 sodium 作用下， 生成 <4-Methyl-phenoxy>-triphenyl-silan
  参考文献：
  名称：

  Transition state for base-catalyzed cleavage of the silicon-oxygen bond

  摘要：

  DOI：

  10.1021/ja00994a018

文献信息

• Toward selective functionalisation of oligosilanes: borane-catalysed dehydrogenative coupling of silanes with thiols
  作者：Daniel J. Harrison、David R. Edwards、Robert McDonald、Lisa Rosenberg

  DOI：10.1039/b806270f

  日期：——

  Among established methods for transforming Si–H bonds, carbonyl hydrosilylation and heterodehydrogenative coupling with alcohols catalysed by B(C6F5)3 are shown to provide exceptionally clean routes to the derivatisation of tetra-substituted disilanes such as [Ph2SiH]2, giving no products resulting from Si–Si bond cleavage. Even higher activity is observed for the borane-catalysed dehydrogenative coupling of silanes with alkyl- and arylthiols, the first examples of such Si–S bond formation in the absence of a transition metal catalyst. Clean, quantitative syntheses of a range of thiosilanes are reported, and the lability of the Si–S linkage toward subsequent alcoholysis is investigated. The crystal structure of 2,3-disila-2,2,3,3-tetramethyl-1,4-benzodioxane is presented.

  在已建立的转化Si–H键的方法中，由B(C6F5)3催化的羰基氢硅化反应和与醇的异脱氢耦合提供了异常清洁的途径，以合成四取代二硅烷（如[Ph2SiH]2），且未产生由于Si–Si键断裂而形成的副产物。对于硼烷催化的硅烷与烷基和芳基硫醇的脱氢耦合，观察到更高的活性，这是在没有过渡金属催化剂的情况下首次实现Si–S键形成。报告了一系列硫硅烷的清洁、定量合成，并研究了Si–S链在随后的醇解中的不稳定性。文中还展示了2,3-二硅-2,2,3,3-四甲基-1,4-苯二噁烷的晶体结构。
• A study of the silanolysis of triphenylsilane and p-methoxyphenol catalysed by (PMe3)4RuH2 and the stoichiometric reactions of (PMe3)4Ru(H)(OC6H4-p-X) (X = Me, OMe) with Ph3SiH
  作者：Melinda J. Burn、Robert G. Bergman

  DOI：10.1016/0022-328x(94)80192-4

  日期：1994.6

  The ruthenium dihydride cis-(PMe3)4Ru(H)2 (1) catalytically converts Ph3SiH and HOC6H4-p-OMe to the alcoholysis products Ph3SiOC6H4-p-OMe and H-2. This reaction was studied kinetically and the rate was found to be first-order in [1], first-order in [HOC6H4-P-OMe], and independent of [Ph3SiH]. The stoichiometric reactions of cis-(PMe3)4Ru(H)(OC6H4-p-X) (X = Me, 2; OMe, 3) with Ph3SiH were also studied in the presence of varying amounts of free para-substituted phenol. In the absence of the free phenol, compounds 2 and 3 reacted with Ph3SiH to give Ph3SiOC6H4-p-X and a compound we believe to be (PMe3)3Ru(H)3(SiPh3) (4). In the presence of large amounts of phenol (> 10 equiv.), (PMe3)4Ru(H)2 (1) was formed. However, at intermediate concentrations of free phenol, compounds 2 and 3 exhibited divergent behavior. Complex 2 gave dihydride 1 in a reaction whose rate was found to be first-order in the concentration of the starting aryloxy hydride 2, first-order in phenol and independent of [Ph3SiH]. In contrast, complex 3 reacted with less than 0.5 equiv. of p-methoxyphenol to form 1, but when approximately 1 equiv. of p-methoxyphenol was added to the solution of 3 and Ph3SiH a mixture of trihydride 4 and dihydride 1 were formed. The mechanisms of these complicated transformations, and their potential relationship to the dihydride-catalyzed silanolysis reaction, are discussed.
• Transition state for base-catalyzed cleavage of the silicon-oxygen bond
  作者：Richard L. Schowen、Kenyon S. Latham

  DOI：10.1021/ja00994a018

  日期：1967.8