1-benzoyl-dibenzofuran | 99329-29-0

• 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-benzoyl-dibenzofuran
• 英文别名: Dibenzofuranyl phenyl ketone；dibenzofuran-1-yl(phenyl)methanone
• CAS: 99329-29-0
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: FQBIYZMGWHXDMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-benzoyl-dibenzofuran 在 三氯化铝 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以19.4%的产率得到1-Benzyl-dibenzofuran
  参考文献：
  名称：

  Keumi, Takashi; Nakamura, Masatoshi; Kitamura, Masao, Journal of the Chemical Society. Perkin transactions II, 1985, p. 909 - 914

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并呋喃 、 苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以0.6%的产率得到1-benzoyl-dibenzofuran
  参考文献：
  名称：

  Keumi, Takashi; Nakamura, Masatoshi; Kitamura, Masao, Journal of the Chemical Society. Perkin transactions II, 1985, p. 909 - 914

  摘要：

  DOI：

文献信息

• Method for synthesizing sodium 2,2,6,6-tetramethylpiperidides
  申请人：KOBELCO ECO-SOLUTIONS CO., LTD.

  公开号：US10836723B2

  公开（公告）日：2020-11-17

  There is a demand for the development of a technique according to which sodium 2,2,6,6-tetramethylpiperidides (Na-TMPs) can be economically and efficiently synthesized through simple operations including a small number of steps under mild conditions in a short period of time. Also, there is a demand for the development of a technique according to which high-quality Na-TMPs that do not contain lithium or lithium compounds such as Li-TMP can be synthesized. The method for synthesizing sodium 2,2,6,6-tetramethylpiperidides includes a step of obtaining sodium 2,2,6,6-tetramethylpiperidides by reacting, in a reaction solvent, 2,2,6,6-tetramethylpiperidines with a dispersion product obtained by dispersing sodium in a dispersion solvent or an organosodium compound having an aromatic ring obtained through a reaction with a dispersion product obtained by dispersing sodium in a dispersion solvent.

  需要开发一种技术，根据这种技术，可以在温和的条件下，通过简单的操作（包括少量步骤），在短时间内经济高效地合成 2,2,6,6-四甲基哌啶钠（Na-TMP）。此外，还需要开发一种技术，根据这种技术可以合成不含锂或锂化合物（如 Li-TMP ）的高质量 Na-TMPs 。合成 2,2,6,6-四甲基哌啶钠的方法包括以下步骤：在反应溶剂中，将 2,2,6,6-四甲基哌啶与通过将钠分散在分散溶剂中得到的分散产物或通过与通过将钠分散在分散溶剂中得到的分散产物反应得到的具有芳香环的有机钠化合物反应，从而得到 2,2,6,6-四甲基哌啶钠。
• Positional reactivity of dibenzofuran in electrophilic substitutions
  作者：Takashi Keumi、Naoto Tomioka、Kozo Hamanaka、Hirohito Kakihara、Toshio Morita、Hidehiko Kitajima、Masahiko Fukushima

  DOI：10.1021/jo00015a020

  日期：1991.7

  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.