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Volumn , Issue 7, 2007, Pages 1067-1070

Straightforward synthesis of highly hydroxylated phloroglucinol-type 3-deoxyanthocyanidins

Author keywords

3 deoxyanthocyanidins; Acid mediated condensation; Heterocycles; Ketones; Phenols

Indexed keywords

3 DEOXYANTHOCYANIDIN DERIVATIVE; ACETIC ACID; APIGENINIDIN; LUTEOLINIDIN; PHLOROGLUCINOL DERIVATIVE; PIGMENT; TRICETANIDIN; UNCLASSIFIED DRUG;

EID: 34248182428     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977433     Document Type: Article
Times cited : (16)

References (38)
  • 12
    • 34248148970 scopus 로고    scopus 로고
    • Darmenton, P.; Philippe, M. FR 2757383, 1996; Chem. Abstr. 1998, 129, 140458n.
    • (a) Darmenton, P.; Philippe, M. FR 2757383, 1996; Chem. Abstr. 1998, 129, 140458n.
  • 21
    • 0000678144 scopus 로고
    • For a review on the synthesis of anthocyanidins, see
    • For a review on the synthesis of anthocyanidins, see: Iacobucci, G. A.; Sweeny, J. G. Tetrahedron 1983, 39, 3005.
    • (1983) Tetrahedron , vol.39 , pp. 3005
    • Iacobucci, G.A.1    Sweeny, J.G.2
  • 29
    • 36649009448 scopus 로고    scopus 로고
    • A similar approach, using sulfuric acid, was mentioned in the early fifties and was, surprisingly, reported only once thereafter: (a) Johnson, A. W.; Melhuish, R. R. J. Chem. Soc. 1947, 346.
    • A similar approach, using sulfuric acid, was mentioned in the early fifties and was, surprisingly, reported only once thereafter: (a) Johnson, A. W.; Melhuish, R. R. J. Chem. Soc. 1947, 346.
  • 36
    • 34248192187 scopus 로고    scopus 로고
    • Apigeninidin Trimethylether Hexafluorophosphate (8) Purple powder; yield 93, mp 201°C. IR(KBr, 1652, 1640 (s,C=O, 1600, 1569, 1506, 1456, 1436, 1378, 1339, 1241, 1124, 1052, 834 (m, P-F) cm-1. UV/Vis (MeOH/5% 1 N HC1, λmax (ε, 266 (24900, 394 (18000, 460 nm (13600 M-1cm-1, 1H NMR [300 MHz, CD3CN-TFA-d1, 1, δ, 3.96 (3 H, s, OCH3, 4.07 (3 H, s, OCH3, 4.09 (3 H, s, OCH 3, 6.80 (1 H, d, J, 2.2 Hz, 7.19 (2 H, m, 7.23 (1 H, dd, J, 2.2, 0.7 Hz, 8.05 (1 H, d, J, 8.5 Hz, 8.32 (2 H, m, 9.07 (1 H, dd, J, 8.5 Hz, 5 J, 0.7 Hz, 13C NMR [75 MHz, CD3CN-TFA-d1, 1, δ, 55.9, 57.0, 57.2 (OCH3, 93.4, 99.8, 111.3, 113.4, 115.8, 120.8, 131.9, 148.7, 158.8, 159.0, 167.0, 171.4, 171.7. MS (ESI, positive mode, 297 100, M, HR
    • +]. HRMS (ESI): m/z calcd: 297.1121; found: 297.1109.
  • 37
    • 34248167481 scopus 로고    scopus 로고
    • Chrysinidin Hexafluorophosphate (12) Orange powder; yield 91, IR (KBr, 3412 (s, br, OH, 1642 (s, C=O, 1580, 1563, 1541, 1381, 1340, 1269, 1239, 1203, 1193, 835 (m, P-F) cm-1. UV/Vis (MeOH/5% 1 N HCl, λmax (ε, 274 (35400, 474 nm (36200 M -1cm-1, 1H NMR [300 MHz, CD 3CN-TFA-d1 (1, δ, 6.81 (1 H, d, J, 2.2 Hz, 7.11 (1 H, dd, J, 2.2, 0.7 Hz, 7.72 (2 H, m, 7.84 (1 H, m, 8.13 (1 H, d, J, 8.4 Hz, 8.35 (2 H, m, 9.25 (1 H, dd, J, 8.4, 0.7 Hz, 13C NMR [75 MHz, CD3CN-TFA-d1 (1, δ, 95.7, 102.9, 111.2, 114.4, 128.9, 129.1, 130.0, 135.8, 150.5, 158.4, 159.4, 171.1, 171.4. MS (ESI, positive mode, 239 (100, M, HRMS ESI, m/z calcd: 239.0703; found: 239.0696
    • +]. HRMS (ESI): m/z calcd: 239.0703; found: 239.0696.
  • 38
    • 34248178372 scopus 로고    scopus 로고
    • All synthesized compounds exhibit NMR spectroscopic data identical to those previously reported in the literature.10-12
    • 10-12


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.