1,3-bis[2,6-di(propan-2-yl)phenyl]-4-methyl-6-methylidene-2'-phenylspiro[1,3,2-diazasiline-2,3'-1H-1,2,3-benzodiazasilole] | 1280212-38-5

• 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: 1,3-bis[2,6-di(propan-2-yl)phenyl]-4-methyl-6-methylidene-2'-phenylspiro[1,3,2-diazasiline-2,3'-1H-1,2,3-benzodiazasilole]
• CAS: 1280212-38-5
• 化学式: C₄₁H₅₀N₄Si
• 分子量: 626.96
• InChiKey: GPFJWXIVEWKWAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  21.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-bis-(2,6-diisopropyl-phenyl)-6-methyl-4-methylene-1,2,3,4-tetrahydro-[1,3,2]diazasiline 、 1,2-二苯肼 以 正己烷 为溶剂， 反应 12.0h， 以70%的产率得到1,3-bis[2,6-di(propan-2-yl)phenyl]-4-methyl-6-methylidene-2'-phenylspiro[1,3,2-diazasiline-2,3'-1H-1,2,3-benzodiazasilole]
  参考文献：
  名称：

  Formation of Silicon Centered Spirocyclic Compounds: Reaction of N-Heterocyclic Stable Silylene with Benzoylpyridine, Diisopropyl Azodicarboxylate, and 1,2-Diphenylhydrazine

  摘要：

  Three silicon centered spirocyclic compounds 1-3, possessing silicon fused six- and five-membered rings have been prepared by the reaction of NHSi (L) [L = CH{(C=CH2)-(CMe)(2,6-iPr(2)C(6)H(3)N)(2)}Si] with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine, respectively, in a 1:1 ratio. The three spirocyclic compounds. (1 3) were obtained by three different pathways. The reaction of L with benzoylpyridine leads to the activation of the pyridine ring, and dearomatization occurred. Treatment of diisopropyl azodicarboxylate with L favors a [1 + 4]- rather than a [1 + 2]-cycloaddition product, and the azo compound was converted to hydrazone derivative. Finally the reaction of 1,2-diphenylhydrazine and L results in the elimination of hydrogen by activating one of the C-H bonds present in the phenyl ring. All three complexes 1-3 were characterized by single crystal X-ray structural analysis, NMR spectroscopy, EI-MS spectrometry, and elemental analysis. In addition the optimized structures of probable products and possible intermediates were investigated using density functional theory (DFT) calculations.

  DOI：

  10.1021/ic102566c

文献信息

• Formation of Silicon Centered Spirocyclic Compounds: Reaction of N-Heterocyclic Stable Silylene with Benzoylpyridine, Diisopropyl Azodicarboxylate, and 1,2-Diphenylhydrazine
  作者：Ramachandran Azhakar、Sankaranarayana Pillai Sarish、Gašper Tavčar、Herbert W. Roesky、Jakob Hey、Dietmar Stalke、Debasis Koley

  DOI：10.1021/ic102566c

  日期：2011.4.4

  Three silicon centered spirocyclic compounds 1-3, possessing silicon fused six- and five-membered rings have been prepared by the reaction of NHSi (L) [L = CH(C=CH2)-(CMe)(2,6-iPr(2)C(6)H(3)N)(2)}Si] with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine, respectively, in a 1:1 ratio. The three spirocyclic compounds. (1 3) were obtained by three different pathways. The reaction of L with benzoylpyridine leads to the activation of the pyridine ring, and dearomatization occurred. Treatment of diisopropyl azodicarboxylate with L favors a [1 + 4]- rather than a [1 + 2]-cycloaddition product, and the azo compound was converted to hydrazone derivative. Finally the reaction of 1,2-diphenylhydrazine and L results in the elimination of hydrogen by activating one of the C-H bonds present in the phenyl ring. All three complexes 1-3 were characterized by single crystal X-ray structural analysis, NMR spectroscopy, EI-MS spectrometry, and elemental analysis. In addition the optimized structures of probable products and possible intermediates were investigated using density functional theory (DFT) calculations.