2-phenacetyl-dibenzofuran | 135075-79-5

• 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-phenacetyl-dibenzofuran
• 英文别名: 1-dibenzofuran-2-yl-2-phenyl-ethanone；1-Dibenzofuran-2-yl-2-phenyl-aethanon；1-Dibenzofuran-2-yl-2-phenylethanone
• CAS: 135075-79-5
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: XYXKAZBSUZYBFM-UHFFFAOYSA-N

物化性质

• 沸点：
  467.1±20.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenacetyl-dibenzofuran 、 phenylmagnesium bromide 在 乙醚 作用下， 生成 2-stilben-α-yl-dibenzofuran
  参考文献：
  名称：

  Buu-Hoi; Royer, Recueil des Travaux Chimiques des Pays-Bas, 1948, vol. 67, p. 175,186

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并呋喃 、 苯乙酰氯 在 三氯化铝 作用下， 以24%的产率得到2-phenacetyl-dibenzofuran
  参考文献：
  名称：

  Positional reactivity of dibenzofuran in electrophilic substitutions

  摘要：

  Isomer distributions of dibenzofuran (DBF) in Friedel-Crafts acylations, Friedel-Crafts alkylations, and nitrations have been determined. The 2- and 3-positions of DBF represents most of the total reactivity. However, the ratio of 2- to 3-isomers greatly varied, depending on the nature of the electrophile. The positional reactivities have been found to be in the following sequence: 2- > 3- > 1- > 4-positions for Friedel-Crafts acylations, Friedel-Crafts benzylations, and nitrations with alkyl nitrate/Lewis acid or nitronium tetrafluoroborate. The ratios for acylations varied over a range from 13.1 to 2.9, while for benzylations and nitrations from 2.0 to 1.0. In contrast, for nitrations of DBF with nitric acid a different reactivity order was found: 3- > 2- > 1- > 4-, with the ratio varying from 0.8 to 0.03 depending on the nature of solvents used. The selectivity for the 3-substitution increased with increase in nitronium ion-like character of nitrating reagents. In particular, nitration with nitric acid in dichloromethane gave mostly 3-nitro-DBF (95% of the four possible isomeric mixture). The charge-transfer nitration with tetranitromethane under the UV irradiation has shown a similar isomer distribution to that in nitration with nitric acid. The MNDO calculations predicts that the late transition-state model (by sigma-complex) favors reactions at the 2-position while the early transition-state model (by HOMO electron density) leads to the 3-substitution.

  DOI：

  10.1021/jo00015a020

文献信息

• Broad Synthesis of Disubstituted Dihydrofuran-Fused [60]Fullerene Derivatives via Cu(I)/Ag(I)-Mediated Synergistic Annulation Reaction
  作者：Shilu Xia、Tong-Xin Liu、Pengling Zhang、Jinliang Ma、Qingfeng Liu、Nana Ma、Zhiguo Zhang、Guisheng Zhang

  DOI：10.1021/acs.joc.7b02848

  日期：2018.1.19

  annulation reaction of [60]fullerene with diarylethanones, benzoylacetonitriles, and β-dicarbonyl compounds has been developed for the direct construction of diverse disubstituted dihydrofuran-fused [60]fullerene derivatives. This transformation exhibits a remarkably broad substrate scope and functional group tolerance and provides a useful method to a scarce class of fullerene derivatives.

  已开发出新颖且有效的Cu（I）/ Ag（I）介导的[60]富勒烯与二芳烃酮，苯甲酰基乙腈和β-二羰基化合物的协同环化反应，用于直接构建不同的二取代的二取代二氢呋喃稠合的[60]富勒烯衍生品。该转化表现出非常宽的底物范围和官能团耐受性，并为稀有种类的富勒烯衍生物提供了一种有用的方法。