2-(4-methylbenzoyl)-dibenzofuran | 135075-78-4

• 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: 2-(4-methylbenzoyl)-dibenzofuran
• 英文别名: dibenzofuran-2-yl(p-tolyl)methanone；Dibenzofuran-2-yl-(4-methylphenyl)methanone
• CAS: 135075-78-4
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: UCGHJBJFUXJAIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 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-(4-methylbenzoyl)-dibenzofuran 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 以52%的产率得到2-(4-methylbenzyl)-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
• 作为产物：
  描述：

  二苯并呋喃 、 对甲基苯甲酰氯 在 三氯化铝 作用下， 以27%的产率得到2-(4-methylbenzoyl)-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

• Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using 2-Chloroimidazolium Chloride as a Coupling Reagent
  作者：Yan Zhang、Yuan-Hua Wang、Qi-Wei Wang、Wei-Xiang Zheng、Jing Zhong、Yi-Ting Yang、Meluze Luobu

  DOI：10.1055/a-1848-3399

  日期：2022.10

  Carboxylic acids are an abundant and structurally diverse class of commercially available materials, which are commonly used as stable reagents in organic synthesis. The Suzuki–Miyaura coupling reaction directly using carboxylic acid as a substrate has been rarely reported. Here, we report an efficient coupling reaction of carboxylic acids with arylboronic acids in toluene in the presence of IPrCl-Cl

  羧酸是一种丰富且结构多样的市售材料，通常用作有机合成中的稳定试剂。很少报道直接使用羧酸作为底物的 Suzuki-Miyaura 偶联反应。在此，我们报道了在 IPrCl-Cl、Pd(OAc) 2、PPh 3和 K 3 PO 4 ·7H 2 O存在下，羧酸与芳基硼酸在甲苯中在 90 °C 下的有效偶联反应，得到相应的芳基酮。