Anthraquinon-2-ylethyl-1′,2′-diol (Aqe-diol) as a new photolabile protecting group for aldehydes and ketones

被引：18
|
作者：
Yu, Jing-yu [1 ]
Tang, Wen-Jian [1 ]
Wang, Hong-Bo [1 ]
Song, Qin-Hua [1 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
来源：
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 2007年 / 185卷 / 01期
基金：
中国国家自然科学基金;
关键词：
photolabile protecting groups; 2-(1,2-dihydroxyethyl) anthraquinone; aldehydes and ketones; photochemistry;
D O I：
10.1016/j.jphotochem.2006.05.010
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A new photolabile protecting group for aldehydes and ketones, 2-(1,2-dihydroxyethyl) anthraquinone (Aqe-diol) and four caged compounds have been prepared and their photochemistry investigated. Upon 350 nm light irradiation, the caged compounds 2a-d in CH3CN-H2O solution can efficiently release the carbonyl compounds (conversion rate 60-90%), and their uncaging quantum efficiencies were measured, ranging from 0.03 to 0.09. On the basis of HPLC analysis and quenching experiments, a mechanism of the uncaging reaction was suggested. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码：101 / 105
页数：5
相关论文
共 50 条
  • [1] Bhc-diol as a photolabile protecting group for aldehydes and ketones
    Lu, M
    Fedoryak, OD
    Moister, BR
    Dore, TM
    ORGANIC LETTERS, 2003, 5 (12) : 2119 - 2122
  • [2] PREPARATION OF A POLYMER-SUPPORTED DIOL AND ITS USE IN ISOLATING ALDEHYDES AND KETONES FROM MIXTURES AND AS A PROTECTING GROUP FOR ALDEHYDES AND KETONES
    HODGE, P
    WATERHOUSE, J
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10): : 2319 - 2323
  • [3] Bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol: a new and efficient photolabile protecting group for aldehydes and ketones
    Kantevari, S
    Narasimahji, CV
    Mereyala, HB
    TETRAHEDRON, 2005, 61 (24) : 5849 - 5854
  • [4] NEW SYNTHESIS OF 1,3-DIOL AND 2,4-DIOL
    WARWEL, S
    SCHMITT, G
    HOMMINGA, E
    CHEMIE INGENIEUR TECHNIK, 1972, 44 (22) : 1283 - &
  • [5] The N-(2-acetoxyethyl) group as a new photolabile protecting group
    Cossy, J
    Rakotoarisoa, H
    TETRAHEDRON LETTERS, 2000, 41 (13) : 2097 - 2099
  • [6] Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): A new photochemically removable protecting group for alcohols
    Furuta, T
    Hirayama, Y
    Iwamura, M
    ORGANIC LETTERS, 2001, 3 (12) : 1809 - 1812
  • [7] 2-(1′-Hydroxyethyl)-anthraquinone as a photolabile protecting group for carboxylic acids
    Ren, Ming-Guang
    Bi, Nai-Min
    Mao, Mao
    Song, Qin-Hua
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2009, 204 (01) : 13 - 18
  • [8] Trimerization of aliphatic aldehydes to 1,3-diol monoesters catalyzed by Cp*2Sm(thf)2
    Miyano, A
    Tashiro, D
    Kawasaki, Y
    Sakaguchi, S
    Ishii, Y
    TETRAHEDRON LETTERS, 1998, 39 (38) : 6901 - 6902
  • [9] A NEW AND EFFICIENT METHOD FOR THE RESOLUTION OF 1,1'-BINAPHTHALENE-2,2'-DIOL
    BRUNEL, JM
    BUONO, G
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25): : 7313 - 7314
  • [10] A new and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diol:: Resolution of racemic [1,1′-binaphthalene]-2,2′-diol with threo-(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol-cyclohexanone condensate
    Liu, DJ
    Shan, ZX
    Liu, F
    Xiao, C
    Lu, GJ
    Qin, JG
    HELVETICA CHIMICA ACTA, 2003, 86 (01) : 157 - 163
12345