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Volumn 7, Issue 2-4, 2003, Pages 265-271

Temperature dependent photochemical cleavage of 2,5-dimethylphenacyl esters

Author keywords

Microwave; Phenacyl esters; Photochemistry; Protecting group; Synthesis

Indexed keywords

2,5 DIMETHYLPHENACYL ESTER; ALCOHOL; BENZENE; BENZOIC ACID; CARBOXYLIC ACID; ESTER; METHANOL; ORGANIC COMPOUND; SOLVENT; UNCLASSIFIED DRUG;

EID: 0345825855     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006862.98763.dd     Document Type: Article
Times cited : (12)

References (40)
  • 3
    • 0000576453 scopus 로고    scopus 로고
    • Photoremovable protecting groups: Reaction mechanisms and applications
    • Pelliccioli, A. P. and Wirz, J., Photoremovable protecting groups: reaction mechanisms and applications, Photochem. Photobiol. Sci., 1 (2002) 441-458.
    • (2002) Photochem. Photobiol. Sci. , vol.1 , pp. 441-458
    • Pelliccioli, A.P.1    Wirz, J.2
  • 4
    • 0036007052 scopus 로고    scopus 로고
    • Photolabile protecting groups and linkers
    • Bochet, C. G., Photolabile protecting groups and linkers, J. Chem. Soc.-Perkin Trans. 1 (2002) 125-142.
    • (2002) J. Chem. Soc.-Perkin Trans. , vol.1 , pp. 125-142
    • Bochet, C.G.1
  • 6
    • 0026108692 scopus 로고
    • Light-directed spatially addressable parallel chemical synthesis
    • Fodor, S. P. A., Read, J. L., Pirrung, M. C., Stryer, L., Lu, A. T. and Solas, D., Light-directed, spatially addressable parallel chemical synthesis, Science, 251 (1991) 767-773.
    • (1991) Science , vol.251 , pp. 767-773
    • Fodor, S.P.A.1    Read, J.L.2    Pirrung, M.C.3    Stryer, L.4    Lu, A.T.5    Solas, D.6
  • 7
    • 0032884952 scopus 로고    scopus 로고
    • Solid phase synthesis - Designer linkers for combinatorial chemistry: A review
    • Gordon, K. and Balasubramanian, S., Solid phase synthesis - designer linkers for combinatorial chemistry: a review, J. Chem. Technol. Biotechnol., 74 (1999) 835-851.
    • (1999) J. Chem. Technol. Biotechnol. , vol.74 , pp. 835-851
    • Gordon, K.1    Balasubramanian, S.2
  • 8
    • 0033683359 scopus 로고    scopus 로고
    • Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry
    • Guillier, F., Orain, D. and Bradley, M., Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry, Chem. Rev., 100 (2000) 2091-2157.
    • (2000) Chem. Rev. , vol.100 , pp. 2091-2157
    • Guillier, F.1    Orain, D.2    Bradley, M.3
  • 9
    • 0001238134 scopus 로고    scopus 로고
    • Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters
    • Banerjee, A. and Falvey, D. E., Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters, J. Org. Chem., 62 (1997) 6245-6251.
    • (1997) J. Org. Chem. , vol.62 , pp. 6245-6251
    • Banerjee, A.1    Falvey, D.E.2
  • 10
    • 0030603031 scopus 로고    scopus 로고
    • p-Hydroxyphenacyl ATP: A new phototrigger
    • Givens, R. S. and Park, C. H., p-Hydroxyphenacyl ATP: A new phototrigger, Tetrahedron Lett., 37 (1996) 6259-6262.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6259-6262
    • Givens, R.S.1    Park, C.H.2
  • 11
    • 0034728648 scopus 로고    scopus 로고
    • New phototriggers 9: p-hydroxyphenacyl as a C-terminal photoremovable protecting group for oligopeptides
    • Givens, R. S., Weber, J. F. W., Conrad, P. G., Orosz, G., Donahue, S. L. and Thayer, S. A., New phototriggers 9: p-hydroxyphenacyl as a C-terminal photoremovable protecting group for oligopeptides, J. Am. Chem. Soc., 122 (2000) 2687-2697.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2687-2697
    • Givens, R.S.1    Weber, J.F.W.2    Conrad, P.G.3    Orosz, G.4    Donahue, S.L.5    Thayer, S.A.6
  • 12
    • 0442295210 scopus 로고    scopus 로고
    • 2,5-Dimethylphenacyl as a new photoreleasable protecting group for carboxylic acids
    • Klan, P., Zabadal, M. and Heger, D., 2,5-Dimethylphenacyl as a new photoreleasable protecting group for carboxylic acids, Org. Lett., 2 (2000) 1569-1571.
    • (2000) Org. Lett. , vol.2 , pp. 1569-1571
    • Klan, P.1    Zabadal, M.2    Heger, D.3
  • 13
    • 0035892201 scopus 로고    scopus 로고
    • 2,5-Dimethylphenacyl esters: A photoremovable protecting group for carboxylic acids
    • Zabadal, M., Pelliccioli, A. P., Klan, P. and Wirz, J., 2,5-Dimethylphenacyl esters: A photoremovable protecting group for carboxylic acids, J. Phys. Chem. A, 105 (2001) 10329-10333.
    • (2001) J. Phys. Chem. A , vol.105 , pp. 10329-10333
    • Zabadal, M.1    Pelliccioli, A.P.2    Klan, P.3    Wirz, J.4
  • 14
    • 0038476233 scopus 로고    scopus 로고
    • 2,5-Dimethylphenacyl esters: A photoremovable protecting group forphosphates and sulfonic acids
    • Klan, P., Pelliccioli, A. P., Pospisil, T. and Wirz, J., 2,5-Dimethylphenacyl esters: A photoremovable protecting group forphosphates and sulfonic acids, Photochem. Photobiol. Sci., 1 (2002) 920-923.
    • (2002) Photochem. Photobiol. Sci. , vol.1 , pp. 920-923
    • Klan, P.1    Pelliccioli, A.P.2    Pospisil, T.3    Wirz, J.4
  • 15
    • 0034807924 scopus 로고    scopus 로고
    • Photorelease of HCl from o-methylphenacyl chloride proceeds through the Z-xylylenol
    • Pelliccioli, A. P., Klan, P. P., Zabadal, M. and Wirz, J., Photorelease of HCl from o-methylphenacyl chloride proceeds through the Z-xylylenol, J. Am. Chem. Soc., 123 (2001) 7931-7932.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7931-7932
    • Pelliccioli, A.P.1    Klan, P.P.2    Zabadal, M.3    Wirz, J.4
  • 16
    • 1842312507 scopus 로고
    • Applications of microwave-energy in organic-chemistry - A review
    • Abramovitch, R. A., Applications of microwave-energy in organic-chemistry - A review, Org. Prep. Proced. Int., 23 (1991) 685-711.
    • (1991) Org. Prep. Proced. Int. , vol.23 , pp. 685-711
    • Abramovitch, R.A.1
  • 18
    • 0001350333 scopus 로고    scopus 로고
    • Microwave chemistry
    • Galema, S. A., Microwave chemistry, Chem. Soc. Rev., 26 (1997) 233-238.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 233-238
    • Galema, S.A.1
  • 20
    • 1642579961 scopus 로고    scopus 로고
    • Microwave-Assisted Combinatorial Chemistry
    • A. Loupy (ed.), Wiley-WCH, Weinheim
    • Kappe, C. O. and Stadler, A., Microwave-Assisted Combinatorial Chemistry, in A. Loupy (ed.), Microwaves in Organic Synthesis, Wiley-WCH, Weinheim, 2002.
    • (2002) Microwaves in Organic Synthesis
    • Kappe, C.O.1    Stadler, A.2
  • 21
    • 0347725842 scopus 로고    scopus 로고
    • Microwave Photochemistry
    • A. Loupy (ed.), Wiley-WCH, Weinheim
    • Klan, P. and Cirkva, V., Microwave Photochemistry, in A. Loupy (ed.), Microwaves in Organic Synthesis, Wiley-WCH, Weinheim, 2002.
    • (2002) Microwaves in Organic Synthesis
    • Klan, P.1    Cirkva, V.2
  • 22
    • 0037462260 scopus 로고    scopus 로고
    • Photochemistry of alkyl aryl ketones on alumina, silica-gel and water ice surfaces
    • Literak, J., Klan, P., Heger, D. and Loupy, A., Photochemistry of alkyl aryl ketones on alumina, silica-gel and water ice surfaces, J. Photochem. Photobiol. A-Chem., 154 (2003) 155-159.
    • (2003) J. Photochem. Photobiol. A-Chem. , vol.154 , pp. 155-159
    • Literak, J.1    Klan, P.2    Heger, D.3    Loupy, A.4
  • 23
    • 0002585361 scopus 로고    scopus 로고
    • The electrodeless discharge lamp: A prospective tool for photochemistry - Part 2. Scope and limitation
    • Literak, J. and Klan, P., The electrodeless discharge lamp: a prospective tool for photochemistry - Part 2. Scope and limitation, J. Photochem. Photobiol. A-Chem., 137 (2000) 29-35.
    • (2000) J. Photochem. Photobiol. A-Chem. , vol.137 , pp. 29-35
    • Literak, J.1    Klan, P.2
  • 25
    • 0043205163 scopus 로고    scopus 로고
    • The electrodeless discharge lamp: A prospective tool for photochemistry Part 3. The microwave photochemistry reactor
    • Klan, P., Hajek, M. and Cirkva, V., The electrodeless discharge lamp: a prospective tool for photochemistry Part 3. The microwave photochemistry reactor, J. Photochem. Photobiol. A-Chem., 140 (2001) 185-189.
    • (2001) J. Photochem. Photobiol. A-Chem. , vol.140 , pp. 185-189
    • Klan, P.1    Hajek, M.2    Cirkva, V.3
  • 26
    • 0043205246 scopus 로고    scopus 로고
    • Molecular photochemical thermometers: Investigation of microwave superheating effects by temperature dependent photochemical processes
    • Klan, P., Literak, J. and Relich, S., Molecular photochemical thermometers: investigation of microwave superheating effects by temperature dependent photochemical processes, J. Photochem. Photobiol. A-Chem., 143 (2001) 49-57.
    • (2001) J. Photochem. Photobiol. A-Chem. , vol.143 , pp. 49-57
    • Klan, P.1    Literak, J.2    Relich, S.3
  • 27
    • 0039837328 scopus 로고    scopus 로고
    • The electrodeless discharge lamp: A prospective tool for photochemistry
    • Klan, P., Literak, J. and Hajek, M., The electrodeless discharge lamp: a prospective tool for photochemistry, J. Photochem. Photobiol. A-Chem., 128 (1999) 145-149.
    • (1999) J. Photochem. Photobiol. A-Chem. , vol.128 , pp. 145-149
    • Klan, P.1    Literak, J.2    Hajek, M.3
  • 28
    • 0001489322 scopus 로고    scopus 로고
    • Direct photolysis of phenacyl protecting groups studied by laser flash photolysis: An excited state hydrogen atom abstraction pathway leads to formation of carboxylic acids and acetophenone
    • Banerjee, A. and Falvey, D. E., Direct photolysis of phenacyl protecting groups studied by laser flash photolysis: An excited state hydrogen atom abstraction pathway leads to formation of carboxylic acids and acetophenone, J. Am. Chem. Soc., 120 (1998) 2965-2966.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2965-2966
    • Banerjee, A.1    Falvey, D.E.2
  • 29
    • 0030230439 scopus 로고    scopus 로고
    • Hydrogen vs electron transfer mechanisms in the chain decomposition of phenacyl bromides. Use of isotopic labeling as a mechanistic probe
    • Renaud, J. and Scaiano, J. C., Hydrogen vs electron transfer mechanisms in the chain decomposition of phenacyl bromides. Use of isotopic labeling as a mechanistic probe, Can. J. Chem. Rev. Can. Chim., 74 (1996) 1724-1730.
    • (1996) Can. J. Chem. Rev. Can. Chim. , vol.74 , pp. 1724-1730
    • Renaud, J.1    Scaiano, J.C.2
  • 30
    • 0001238134 scopus 로고    scopus 로고
    • Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters
    • Banerjee, A. and Falvey, D. E., Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters, J. Org. Chem., 62 (1997) 6245-6251.
    • (1997) J. Org. Chem. , vol.62 , pp. 6245-6251
    • Banerjee, A.1    Falvey, D.E.2
  • 31
    • 0032565843 scopus 로고    scopus 로고
    • Protecting group release through photoinduced electron transfer: Wavelength control through sensitized irradiation
    • Banerjee, A., Lee, K., Yu, Q., Fang, A. G. and Falvey, D. E., Protecting group release through photoinduced electron transfer: Wavelength control through sensitized irradiation, Tetrahedron Lett., 39 (1998) 4635-4638.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4635-4638
    • Banerjee, A.1    Lee, K.2    Yu, Q.3    Fang, A.G.4    Falvey, D.E.5
  • 32
    • 0001368167 scopus 로고    scopus 로고
    • Orthogonal photolysis of protecting groups
    • Bochet, C. G., Orthogonal photolysis of protecting groups, Angew. Chem. Int. Edit., 40 (2001) 2071-2073.
    • (2001) Angew. Chem. Int. Edit. , vol.40 , pp. 2071-2073
    • Bochet, C.G.1
  • 33
    • 0029799743 scopus 로고    scopus 로고
    • Protecting group strategies in organic synthesis
    • Schelhaas, M. and Waldmann, H., Protecting group strategies in organic synthesis, Angew. Chem.-Int. Edit. Engl., 35 (1996) 2056-2083.
    • (1996) Angew. Chem.-Int. Edit. Engl. , vol.35 , pp. 2056-2083
    • Schelhaas, M.1    Waldmann, H.2
  • 34
    • 0000414181 scopus 로고    scopus 로고
    • Two useful photolabile surfaces for solid-phase synthesis
    • Ryba, T. D. and Harran, P. G., Two useful photolabile surfaces for solid-phase synthesis, Org. Lett., 2 (2000) 851-853.
    • (2000) Org. Lett. , vol.2 , pp. 851-853
    • Ryba, T.D.1    Harran, P.G.2
  • 35
    • 0001125895 scopus 로고    scopus 로고
    • Model studies for new o-nitrobenzyl photolabile linkers: Substituent effects on the rates of photochemical cleavage
    • Holmes, C. P., Model studies for new o-nitrobenzyl photolabile linkers: Substituent effects on the rates of photochemical cleavage, J. Org. Chem., 62 (1997) 2370-2380.
    • (1997) J. Org. Chem. , vol.62 , pp. 2370-2380
    • Holmes, C.P.1
  • 36
    • 0001216513 scopus 로고
    • Reagents for combinatorial organic-synthesis - Development of a new O-nitrobenzyl photolabile linker for solid-phase synthesis
    • Holmes, C. P. and Jones, D. G., Reagents for combinatorial organic-synthesis - Development of a new O-nitrobenzyl photolabile linker for solid-phase synthesis, J. Org. Chem., 60 (1995) 2318-2319.
    • (1995) J. Org. Chem. , vol.60 , pp. 2318-2319
    • Holmes, C.P.1    Jones, D.G.2
  • 37
    • 0000820924 scopus 로고
    • A New phenacyl-type handle for polymer supported peptide-synthesis
    • Bellof, D. and Mutter, M., A new phenacyl-type handle for polymer supported peptide-synthesis, Chimia, 39 (1985) 317-320.
    • (1985) Chimia , vol.39 , pp. 317-320
    • Bellof, D.1    Mutter, M.2
  • 38
    • 0037059435 scopus 로고    scopus 로고
    • Practical synthesis of a dithiane-protected 3′,5′ -dialkoxybenzoin photolabile safety-catch linker for solid-phase organic synthesis
    • Cano, M., Ladlow, M. and Balasubramanian, S., Practical synthesis of a dithiane-protected 3′,5′-dialkoxybenzoin photolabile safety-catch linker for solid-phase organic synthesis, J. Org. Chem., 67 (2002) 129-135.
    • (2002) J. Org. Chem. , vol.67 , pp. 129-135
    • Cano, M.1    Ladlow, M.2    Balasubramanian, S.3
  • 39
    • 0001359131 scopus 로고
    • Acylation-alkylation studies, I
    • Hart, R. T. and Tebbe, R. F., Acylation-alkylation studies, I., J. Am. Chem. Soc., 72 (1950) 3286-3287.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 3286-3287
    • Hart, R.T.1    Tebbe, R.F.2
  • 40
    • 0010848354 scopus 로고
    • The reaction of lead tetraacetate with unsymmetrical ketones
    • Moon, S. and Bohm, H., The reaction of lead tetraacetate with unsymmetrical ketones, J. Org. Chem., 37 (1972) 4338-4340.
    • (1972) J. Org. Chem. , vol.37 , pp. 4338-4340
    • Moon, S.1    Bohm, H.2


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