4-acetyl-dibenzofuran | 119490-18-5

• 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: 4-acetyl-dibenzofuran
• 英文别名: 1-(Dibenzo[b,d]furan-4-yl)ethan-1-one；1-dibenzofuran-4-ylethanone
• CAS: 119490-18-5
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: CATAPWNWWJUZJH-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±15.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  氘代溴苯 、 4-acetyl-dibenzofuran 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 反应 0.5h， 以37%的产率得到4-(anthracen-9-yl-1,2,3,4,5,6,7,8-d₈)dibenzo[b,d]furan
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING DEUTERATED ANTHRACENE COMPOUND, REACTION COMPOSITION, DEUTERATED ANTHRACENE COMPOUND AND COMPOSITION
  [FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ D'ANTHRACÈNE DEUTÉRÉ, COMPOSITION DE RÉACTION, COMPOSÉ D'ANTHRACÈNE DEUTÉRÉ ET COMPOSITION
  [KO] 중수소화 안트라센 화합물의 제조방법, 반응 조성물, 중수소화 안트라센 화합물 및 조성물

  摘要：

  本规范书涉及制备含有至少一个卤代苯和化学式为1的化合物的中氢化合物，其中包括合成中氢化蒽化合物的步骤，涉及反应组成物，中氢化蒽化合物和组成物的制备方法。

  公开号：

  WO2022158903A1
• 作为产物：
  描述：

  二苯并呋喃羧酸氯化物 在 甲基锂 作用下， 以54%的产率得到4-acetyl-dibenzofuran
  参考文献：
  名称：

  经典σ-络合物和电荷转移机制在二苯并呋喃亲电芳香取代中位置选择性的显着差异

  摘要：

  二苯并呋喃与硝酸通过电荷转移机制的亲电硝化仅发生在 3-位，另一方面，2-位的取代在酰化中占主导地位，其中经典的 σ-络合物机制很重要。

  DOI：

  10.1246/cl.1988.1285

文献信息

• METAL COMPLEXES
  申请人：Stoessel Philipp

  公开号：US20130082209A1

  公开（公告）日：2013-04-04

  The present invention relates to metal complexes and to elec tronic devices, in particular organic electroluminescent devices, com-pris ing these metal complexes. M(L)n(L′)m (formula 1), where the compound of the gene ral formula (1) contains a moiety M(L)n of the formula (2).

  本发明涉及金属配合物和电子设备，特别是包含这些金属配合物的有机电致发光器件。其中，通式（1）的化合物包含式（2）的M(L)n基团。
• 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.
• Palladium-Catalyzed Acetylation of Arenes
  作者：Stephen D. Ramgren、Neil K. Garg

  DOI：10.1021/ol403570z

  日期：2014.2.7

  A simple method for the preparation of aryl methyl ketones is reported. The transformation involves the Pd-catalyzed coupling of an acyl anion equivalent, acetyltrimethylsilane, with aryl bromides to afford the corresponding acetylated arenes in synthetically useful yields. The methodology is tolerant of heterocycles and provides a new method for arene functionalization.
• US9273080B2
  申请人：——

  公开号：US9273080B2

  公开（公告）日：2016-03-01
• A Remarkable Difference of the Positional Selectivity in Electrophilic Aromatic Substitution of Dibenzofuran between the Classical σ-Complex and Charge-Transfer Mechanisms
  作者：Takashi Keumi、Kozo Hamanaka、Haruo Hasegawa、Naoki Minamide、Yoshinori Inoue、Hidehiko Kitajima

  DOI：10.1246/cl.1988.1285

  日期：1988.8.5

  Electrophilic nitration of dibenzofuran with nitric acid by a charge-transfer mechanism occurs exclusively at the 3-position and on the other hand, substitution at the 2-position predominates in the acylation, in which a classical σ-complex mechanism is important.

  二苯并呋喃与硝酸通过电荷转移机制的亲电硝化仅发生在 3-位，另一方面，2-位的取代在酰化中占主导地位，其中经典的 σ-络合物机制很重要。