A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes

被引：74
作者：
Bychek, Roman [1 ]
Mykhailiuk, Pavel K. [1 ]
机构：
[1] Enamine Ltd, Chervonotkatska 60, UA-02094 Kiev, Ukraine
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 29期
基金：
欧洲研究理事会;
关键词：
Bicyclo[1; 1; 0]butane; 1]pentane; Bioisosteres; Fluorine; CHEMISTRY; PEPTIDE; DESIGN;
D O I：
10.1002/anie.202205103
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
After more than 20 years of trials, a practical scalable approach to fluoro-substituted bicyclo[1.1.1]pentanes (F-BCPs) has been developed. The physicochemical properties of the F-BCPs have been studied, and the core was incorporated into the structure of the anti-inflammatory drug Flurbiprofen in place of the fluorophenyl ring.
引用
收藏
页数：7
相关论文
共 50 条
  • [1] A practical access to fluoroalkylthio(seleno)-functionalized bicyclo[1.1.1]pentanes
    Wu Zhen
    Xu Yaohui
    Liu Jige
    Wu Xinxin
    Zhu Chen
    SCIENCE CHINA-CHEMISTRY, 2020, 63 (08) : 1025 - 1029
  • [2] Synthesis of Enantioenriched α-Chiral Bicyclo[1.1.1]pentanes
    Wong, Marie L. J.
    Mousseau, James J.
    Mansfield, Steven J.
    Anderson, Edward A.
    ORGANIC LETTERS, 2019, 21 (07) : 2408 - 2411
  • [3] Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes
    Livesley, Sarah
    Sterling, Alistair J.
    Robertson, Craig M.
    Goundry, William R. F.
    Morris, James A.
    Duarte, Fernanda
    Aissa, Christophe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (02)
  • [4] Difluoro-Substituted Bicyclo[1.1.1]pentanes for Medicinal Chemistry: Design, Synthesis, and Characterization
    Bychek, Roman M.
    Hutskalova, Valeriia
    Bas, Yuliya P.
    Zaporozhets, Olga A.
    Zozulya, Sergey
    Levterov, Vadym V.
    Mykhailiuk, Pavel K.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) : 15106 - 15117
  • [5] Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
    Shire, Bethany R.
    Anderson, Edward A.
    JACS AU, 2023, 3 (06): : 1539 - 1553
  • [6] Organometallic Bridge Diversification of Bicyclo[1.1.1]pentanes
    Anderson, Joseph M.
    Poole, Darren L.
    Cook, Gemma C.
    Murphy, John A.
    Measom, Nicholas D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (12)
  • [7] Enantioselective C-H functionalization of bicyclo[1.1.1]pentanes
    Garlets, Zachary J.
    Sanders, Jacob N.
    Malik, Hasnain
    Gampe, Christian
    Houk, K. N.
    Davies, Huw M. L.
    NATURE CATALYSIS, 2020, 3 (04) : 351 - 357
  • [8] Synthesis of selenoether and thioether functionalized bicyclo[1.1.1] pentanes
    Wu, Zhen
    Xu, Yaohui
    Wu, Xinxin
    Zhu, Chen
    TETRAHEDRON, 2020, 76 (50)
  • [9] Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes
    Caputo, Dimitri F. J.
    Arroniz, Carlos
    Durr, Alexander B.
    Mousseau, James J.
    Stepan, Antonia F.
    Mansfield, Steven J.
    Anderson, Edward A.
    CHEMICAL SCIENCE, 2018, 9 (23) : 5295 - 5300
  • [10] Visible light-induced gem-difluoroallylation of [1.1.1]propellane to access gem-difluoroallylic bicyclo[1.1.1]pentanes
    Zhu, Hui
    Wu, Shengxing
    Zhu, Bingbin
    Li, Jiacheng
    Lan, Deyou
    Xu, Wenhao
    Xu, Gongcheng
    Zhu, Yu
    Yu, Chuanming
    Jiang, Xinpeng
    CHEMICAL COMMUNICATIONS, 2023, 59 (35) : 5213 - 5216
12345