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Volumn 63, Issue 22, 1998, Pages 8052-8057

Preparation of benzylic α,α-difluoronitriles, -tetrazoles, and -sulfonates via electrophilic fluorination

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EID: 0001090596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981163x     Document Type: Article
Times cited : (45)

References (49)
  • 23
    • 0001029493 scopus 로고    scopus 로고
    • For a review on electrophilic fluorination, see: Rozen, S. Chem. Rev. 1996, 96, 1717.
    • (1996) Chem. Rev. , vol.96 , pp. 1717
    • Rozen, S.1
  • 28
    • 85034166505 scopus 로고    scopus 로고
    • 8c However, we were unable to obtain any appreciable quantities of 20 in pure form using this procedure.
    • 8c However, we were unable to obtain any appreciable quantities of 20 in pure form using this procedure.
  • 40
    • 85034185792 scopus 로고    scopus 로고
    • Sulfonates are completely ionized at physiological pH. Thus, any increase in inhibitor potency of a,a-difluorosulfonates compared to their nonfluorinated or sulfate counterparts would have to be a result of a direct interaction of the fluorines with residues in the enzyme active site, as. appears to be the case with the a-difluorinated phosphonates and PTP's.
    • Sulfonates are completely ionized at physiological pH. Thus, any increase in inhibitor potency of a,a-difluorosulfonates compared to their nonfluorinated or sulfate counterparts would have to be a result of a direct interaction of the fluorines with residues in the enzyme active site, as. appears to be the case with the a-difluorinated phosphonates and PTP's.
  • 49
    • 85034172626 scopus 로고    scopus 로고
    • In conclusion, we have demonstrated that benzylic α,αdifluoronitriles, -tetrazoles, and -sulfonates can be prepared by electrophilic fluorination of benzylic carbanions
    • 18a-d some of which are estrone sulfonates in which the labile S-O bond in the substrate is replaced by a méthylène unit.18d Conversion of these compounds to the α,α-difluorosulfonate derivatives may provide a means of increasing the potency of these compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.