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Volumn 64, Issue 21, 1999, Pages 7988-7995

Hydrolytic stabilization of protected p-hydroxybenzyl halides designed as latent quinone methide precursors

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; BROMINE DERIVATIVE; CHLORIDE; FLUORIDE; HALIDE; QUINONE DERIVATIVE;

EID: 0032723726     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991085t     Document Type: Article
Times cited : (19)

References (70)
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    • (e) Moore, H. W. Science 1977, 197, 527.
    • (1977) Science , vol.197 , pp. 527
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  • 30
    • 33847526452 scopus 로고    scopus 로고
    • Waksclman has recently reported the use of a related compound as a β-Lactamase inhibitor (see ref 3a)
    • Waksclman has recently reported the use of a related compound as a β-Lactamase inhibitor (see ref 3a).
  • 31
    • 0030122802 scopus 로고    scopus 로고
    • Wan and co-workers readily photogenerate quinono methides using laser flash photolysis at 266 nm (Wan, P.; Barker, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C. Can. J. Chem. 1996, 74, 465.); however, this wavelength is not suitable for use in biological systems (see ref 14).
    • (1996) C. Can. J. Chem. , vol.74 , pp. 465
    • Wan, P.1    Barker, B.2    Diao, L.3    Fischer, M.4    Shi, Y.5    Yang6
  • 45
    • 33744644481 scopus 로고    scopus 로고
    • A complete account of the use of the quinone methide generated in these investigations in various alkylation processes will be reported in due course
    • A complete account of the use of the quinone methide generated in these investigations in various alkylation processes will be reported in due course.
  • 48
    • 33744684800 scopus 로고    scopus 로고
    • note
    • (a) Nitration of commercially available 3, 4-dimethoxyacetophenone following the procedure in ref 15c was accomplished in 63% yield, (b) Reduction of the nitro ketone following the procedure in ref 23 was accomplished in 77% yield after recryslallization from water/ethanol.
  • 55
    • 33847501865 scopus 로고    scopus 로고
    • Note also that, even at 55°C, compounds 17a and 18a showed no evidence of hydrolysis after 4-6 days (Table 2)
    • Note also that, even at 55°C, compounds 17a and 18a showed no evidence of hydrolysis after 4-6 days (Table 2).
  • 59
    • 0542443644 scopus 로고
    • This may be compared to a af value of -0.42 for a benzyloxy substituent. Jaffe, H. H. Chem. Rev. 1953, 53, 191.
    • (1953) Chem. Rev. , vol.53 , pp. 191
    • Jaffe, H.H.1
  • 60
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    • -3.
    • -3.
  • 66
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    • Solv-Tek Inc., Berryville, VA.
    • Solv-Tek Inc., Berryville, VA.
  • 67
    • 33847519727 scopus 로고    scopus 로고
    • Millipore Corp., Molsheim, France.
    • Millipore Corp., Molsheim, France.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.