3-(chlorocarbonyl)-dibenzofuran | 61831-09-2

• 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: 3-(chlorocarbonyl)-dibenzofuran
• 英文别名: dibenzofuran-3-carbonyl chloride；Dibenzo[b,d]furan-3-carbonyl chloride
• CAS: 61831-09-2
• 化学式: C₁₃H₇ClO₂
• 分子量: 230.65
• InChiKey: QDMCXIXYSSKSDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(chlorocarbonyl)-dibenzofuran 在 氢氧化钾 、 三氯化铝 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 生成 3-(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：

  3-二苯并呋喃羧酸 在 五氯化磷 作用下， 生成 3-(chlorocarbonyl)-dibenzofuran
  参考文献：
  名称：

  Influence of the Angular Linkage on the Mesomorphic Properties of Cholesteryl Arylbenzoates

  摘要：

  DOI：

  10.1080/00268948208072592

文献信息

• Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight
  作者：Haifang Meng、Huiying Xu、Zhi Zhou、Zhenhao Tang、Yidi Li、Yu Zhou、Wei Yi、Xiaowei Wu

  DOI：10.1039/d2gc02347d

  日期：——

  sustainability and applications. Described herein is a robust and convenient rhodium-catalyzed regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones with salient features including a recyclable catalytic reaction system, unique regioselectivity, gram-scale synthesis with low catalyst loading (e.g., 0.5 mol%), ethanol as the green solvent, air and water compatibility, and

  C-H 活化提供了一种直接的方法来构建新的化学键和特权杂环。然而，由于共同的缺陷，C-H活化在可持续性和应用方面仍然面临着巨大的挑战。本文描述了一种稳健且方便的铑催化区域选择性 C-H 活化/[4 + 2] 环化，用于合成异喹诺酮类药物，其显着特征包括可回收的催化反应系统、独特的区域选择性、具有低催化剂负载量的克级合成（例如, 0.5 mol%), 乙醇作为绿色溶剂, 空气和水相容, 纯化过程简单。基于综合实验和 DFT 研究，阐明了羟基和新戊酰部分在两种底物中的作用、炔丙醇伴侣的额外关键功能以及独特化学选择性的起源。此外，还合理地推导出了与羟基和新戊酰基部分连接的独特氢键网络，用于通过随后的 IMH 分析赋予观察到的反向区域选择性。
• Ruban,E.M.; Kornilov,M.Y., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 2601 - 1605
  作者：Ruban,E.M.、Kornilov,M.Y.

  DOI：——

  日期：——
• METAL COMPLEXES
  申请人：Merck Patent GmbH

  公开号：US20170170413A1

  公开（公告）日：2017-06-15

  The present invention relates to metal complexes and to electronic devices, in particular organic electroluminescent devices, comprising these metal complexes.
• US4611033A
  申请人：——

  公开号：US4611033A

  公开（公告）日：1986-09-09
• US4710562A
  申请人：——

  公开号：US4710562A

  公开（公告）日：1987-12-01