2-Trimethylsilyl-dibenzofuran | 17909-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-Trimethylsilyl-dibenzofuran
• 英文别名: 9-Trimethylsilyl-dibenzofuran；dibenzo[b,d]furan-3-yl-trimethylsilane；3-trimethylsilyldibenzofuran；dibenzofuran-3-yl-trimethyl-silane；Dibenzo[b,d]furan-3-yltrimethylsilane；dibenzofuran-3-yl(trimethyl)silane
• CAS: 17909-49-8
• 化学式: C₁₅H₁₆OSi
• 分子量: 240.377
• InChiKey: DNDICALZDIFTIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-trimethylsilyl-2'-hydroxybiphenyl 在 4,5-二氮芴-9-酮 、 palladium diacetate 、 potassium carbonate 、 sodium 2,4,6-trimethylbenzoate 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 均三甲苯 为溶剂， 反应 24.0h， 以82%的产率得到2-Trimethylsilyl-dibenzofuran
  参考文献：
  名称：

  Synthesis of Dibenzofurans via Palladium-Catalyzed Phenol-Directed C–H Activation/C–O Cyclization

  摘要：

  A practical, Pd(0)/Pd(II)-catalyzed reaction was developed for phenol-directed C-H activation/C-O cyclization using air as an oxidant. The turnover-limiting step of the process was found to be C-O reductive elimination instead of C-H activation. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted dibenzofurans.

  DOI：

  10.1021/ja203335u

文献信息

• Oxidative Cyclization of 2-Arylphenols to Dibenzofurans under Pd(II)/Peroxybenzoate Catalysis
  作者：Ye Wei、Naohiko Yoshikai

  DOI：10.1021/ol202229w

  日期：2011.10.21

  2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis In the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage Is the rate-limiting step of the reaction.
• Synthesis of Dibenzofurans via Palladium-Catalyzed Phenol-Directed C–H Activation/C–O Cyclization
  作者：Bin Xiao、Tian-Jun Gong、Zhao-Jing Liu、Jing-Hui Liu、Dong-Fen Luo、Jun Xu、Lei Liu

  DOI：10.1021/ja203335u

  日期：2011.6.22

  A practical, Pd(0)/Pd(II)-catalyzed reaction was developed for phenol-directed C-H activation/C-O cyclization using air as an oxidant. The turnover-limiting step of the process was found to be C-O reductive elimination instead of C-H activation. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted dibenzofurans.