1-(chlorocarbonyl)-dibenzofuran | 66283-59-8

• 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: 1-(chlorocarbonyl)-dibenzofuran
• 英文别名: dibenzofuran carboxylic acid chloride；dibenzofuran-1-carbonyl chloride
• CAS: 66283-59-8
• 化学式: C₁₃H₇ClO₂
• 分子量: 230.65
• InChiKey: MPXNEKGCULDCPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：

  1-(chlorocarbonyl)-dibenzofuran 在 甲基锂 作用下， 以48%的产率得到1-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

• Substituted N-Aryl-9-Oxo-9H-Fluorene-1-Carboxamides and Analogs as Activators of Caspases and Inducers of Apoptosis
  申请人：Kemnitzer E. William

  公开号：US20080096848A1

  公开（公告）日：2008-04-24

  The present invention is directed to substituted N-aryl-9-oxo-9H-fluorene-1-carboxamides and analogs thereof, represented by the general Formula I: (I) wherein R 1 -R 8 , X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的N-芳基-9-氧代-9H-芴-1-羧酰胺及其类似物，由通式I表示：（I）其中R1-R8、X和Ar的定义如本文所述。本发明还涉及发现具有I式化合物的化合物是caspase的活化剂和凋亡诱导剂。因此，本发明的caspase活化剂和凋亡诱导剂可用于在发生异常细胞的无控制生长和扩散的各种临床情况下诱导细胞死亡。
• 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.
• SUBSTITUTED N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS
  申请人：Cytovia, Inc.

  公开号：EP1804786A2

  公开（公告）日：2007-07-11
• EP1804786A4
  申请人：——

  公开号：EP1804786A4

  公开（公告）日：2008-01-02
• [EN] SUBSTITUTED N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES AND ANALOGS AS ACTIVATOR OF CASPASES AND INDUCERS OF APOPTOSIS<br/>[FR] N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES SUBSTITUES ET ANALOGUES UTILISES COMME ACTIVATEURS DES CASPASES ET INDUCTEURS DE L'APOPTOSE
  申请人：CYTOVIA INC

  公开号：WO2006039356A2

  公开（公告）日：2006-04-13

  The present invention is directed to substituted N-aryl-9-oxo-9H-fluorene-1-carboxamides and analogs thereof, represented by the general Formula I: (I) wherein R1-R8, X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.