Spirocyclic oxetanes:: Synthesis and properties

被引:167
作者
Wuitschik, Georg [2 ]
Rogers-Evans, Mark [1 ]
Buckl, Andreas
Bernasconi, Maurizio
Maerki, Moritz
Godel, Thierry [1 ]
Fischer, Holger [1 ]
Wagner, Bjoern [1 ]
Parrilla, Isabelle [1 ]
Schuler, Franz [1 ]
Schneider, Josef [1 ]
Alker, Andre [1 ]
Schweizer, W. Bernd
Mueller, Klaus [1 ]
Carreira, Erick M. [2 ]
机构
[1] F Hoffmann La Roche & Cie AG, Div Pharmaceut, CH-4070 Basel, Switzerland
[2] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
carbonyl compounds; heterocycles; morpholine; oxetanes; spiro compounds;
D O I
10.1002/anie.200800450
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Presented) Wormholes through chemical space: Spirocyclic oxetanes are described as analogues of morpholine and also as topological siblings of their carbonyl counterparts. They are particularly promising in terms of both their physicochemical properties and the ease with which they can be grafted onto molecular structures. The data collected highlight oxetanes as both the hydrophilic sister of a gem-dimethyl unit and the carbonyl group's lipophilic brother. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4512 / 4515
页数:4
相关论文
共 21 条
  • [1] PENTAERYTHRITOL DERIVATIVES .5. PREPARATION OF DIETHERS OF PENTAERYTHRITOL BY REDUCTION OF ACETALS AND KETALS
    ABDUNNUR, AR
    ISSIDORIDES, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) : 67 - &
  • [2] Berthelot M, 1998, EUR J ORG CHEM, V1998, P925
  • [3] Hydrogen-bond basicity pKHB scale of aldehydes and ketones
    Besseau, F
    Lucon, M
    Laurence, C
    Berthelot, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (01): : 101 - 107
  • [4] Castro Pineiro J.L., 2001, PCT Int. Appl, Patent No. [WO 2001087838 A1, 2001087838]
  • [5] Fluorine-containing donor-acceptor complexes: crystallographic study of the interactions between electronegative atoms (N, O, S) and halogen atoms (I, Br)
    Chu, QL
    Wang, ZM
    Huang, QC
    Yan, CH
    Zhu, SZ
    [J]. NEW JOURNAL OF CHEMISTRY, 2003, 27 (10) : 1522 - 1527
  • [6] MAB, A GENERALLY APPLICABLE MOLECULAR-FORCE FIELD FOR STRUCTURE MODELING IN MEDICINAL CHEMISTRY
    GERBER, PR
    MULLER, K
    [J]. JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 1995, 9 (03) : 251 - 268
  • [7] HOSTE J, 1949, B SOC CHIM BELG, V58, P157
  • [8] KHAZIPOV RK, 1984, IZV VYSSH UCHEBN ZAV, V27, P86
  • [9] Kolb H.C., 2001, ANGEW CHEM, V113, P2056, DOI [10.1002/1521-3757(20010601)113:11, DOI 10.1002/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO
  • [10] 2-W]