1,1,3-三苯基-1-硅杂环丁烷 | 76889-05-9

• 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
• 中文名称: 1,1,3-三苯基-1-硅杂环丁烷
• 英文名称: 1,1,2-triphenylsilacyclobutane
• 英文别名: 1,1,2-Triphenylsiletane
• CAS: 76889-05-9
• 化学式: C₂₁H₂₀Si
• 分子量: 300.475
• InChiKey: DIPRMXGYXJVQAW-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±38.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1,1,3-三苯基-1-硅杂环丁烷 生成 1,1,2-Triphenyl-1-silacyclobut-2-en
  参考文献：
  名称：

  Small-Ring Organosilicon Compounds. III. 1,1,2-Triphenyl-1-silacyclobut-2-ene and 1,1,2-Triphenyl-1-silacyclopent-2-ene

  摘要：

  DOI：

  10.1021/ja01090a027

文献信息

• Thermolyse und photolyse einiger sila- und disilacyclobutane
  作者：Peter Jutzi、Peter Langer

  DOI：10.1016/s0022-328x(00)81868-9

  日期：1980.12

  3-disilacyclobutanes or to polymeric products. A possible intermediate silaalkene could not be stabilized, even in the presence of bulky substituents at the silicon atom. Photolysis of some di- or tri-substituted silacyclobutanes in methanol results in ring opening or in elimination of an alkene with further reaction of the intermediates with the solvent. Photolysis of the 1,1-diphenyl-2-methyl-l-silacyclobutane

  某些1,1-二-或1,1,2-三取代的1-silacyclobutanes的热分解导致1,3-disilacyclobutanes或聚合产物。即使在硅原子上存在大量取代基，可能的中间硅烷基烯烃也无法稳定。一些二或三取代的甲硅烷基环丁烷在甲醇中的光解导致开环或烯烃的消除，以及中间体与溶剂的进一步反应。1,1-二苯基-2-甲基-1-硅环丁烷在环己烷中的光解产生1,1,3,3-四苯基-1,3-二硅环丁烷。讨论了硅或碳原子上取代基对反应路径的影响。1,1,3,3-四甲基-2,4-二苯基-1,3-二硅环丁烷的光解反应通过开环和添加甲醇而发生，而1,1,3,3-四苯基-1，
• The one- and two-photon photochemistry of benzylsilacyclobutanes, acyclic benzylsilanes, and 1,1,2-triphenylsilacyclobutane
  作者：William J Leigh、Thomas R Owens

  DOI：10.1139/v99-249

  日期：2000.11.1

  The photochemistry of several α-silylbenzyl compounds has been investigated in hexane and in methanol solution. Direct photolysis of 1-benzyl-1-methylsilacyclobutane (1) in methanolic hexane solution produces 1-propyl-1-methyl-2,3-benzosilacyclobutene (6) in quantitative yield, by a sequential two-photon process involving the photoactive isotoluene derivative 1-methylene-6-(1-methylsilacyclobutyl)-2,4-cyclohexadiene (13a), which has been identified on the basis of its ¹H NMR and UV absorption spectra. In contrast, direct irradiation of 1-benzyl-1-phenylsilacyclobutane (2) under similar conditions results in the formation of a complex mixture of products consistent with the competing formation of 1-benzyl-1-phenylsilene and benzyl- and 1-phenylsilacyclobutyl radicals. The silene is a transient which has been detected directly by laser flash photolysis of 2 (λ_max = 315 nm, τ ~ 4.5 µs). Free radical formation is shown to be due to secondary photolysis of a second primary product, 1-methylene-6-(1-phenylsilacyclobutyl)-2,4-cyclohexadiene (13b), which has also been detected and identified by static UV absorption (λ_max = 335 nm) and ¹H NMR spectroscopy. In a reaction with some analogy to the acid-catalyzed desilylation of allylsilanes, both 13a and 13b can be intercepted in neutral or acidic methanol solution to yield toluene and 1-methyl- or 1-phenyl-1-methoxysilacyclobutane, respectively. Direct photolysis of benzyldimethylphenylsilane (4) also leads to the formation of the corresponding isotoluene derivative, while benzyltrimethylsilane (3) exhibits negligible photoreactivity. The endocyclic benzylsilane 1,1,2-triphenylsilacyclobutane (5) is shown to undergo competing [2 + 2]-cycloreversion and [1,3]-silyl migration to yield a bicyclic isotoluene analogue, which reacts rapidly with methanol to yield the acyclic methoxysilane reported previously to be the main product of photolysis of this silacyclobutane in methanol solution. Relative quantum yields for isotoluene formation from photolysis of 1-4 and absolute rate constants for methanolysis of several of these compounds under neutral and acidic conditions have also been determined.Key words: photochemistry, organosilicon, benzylsilane, silacyclobutane, silene, kinetics, isotoluene.

  已完成。
• 1,1-Diphenylsilene
  作者：William J. Leigh、Christine J. Bradaric、Gregory W. Sluggett

  DOI：10.1021/ja00065a070

  日期：1993.6