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Volumn , Issue 12, 2008, Pages 1882-1888

Efficient silver-mediated acetalation of β,β′- functionalized chlorins

Author keywords

Acetal; Chlorin; PQQ; Pyrroloquinoline quinine; Silver triflate

Indexed keywords

2 DIAZO 3 OXOCHLORIN DERIVATIVE; 2,2 DIALKOXY 3 OXOCHLORIN DERIVATIVE; ACETAL DERIVATIVE; ACETALOXOCHLORIN DERIVATIVE; MACROCYCLIC COMPOUND; PORPHYRIN DERIVATIVE; SILVER;

EID: 48449085817     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078505     Document Type: Article
Times cited : (5)

References (48)
  • 33
    • 48449092304 scopus 로고    scopus 로고
    • 2, and EtOAc.
    • 2, and EtOAc.
  • 34
    • 48449106521 scopus 로고    scopus 로고
    • Product Characterization Data: Cu3a: MALDI (TOF, mlz (isotope pattern, 807.2 [M, HRMS (ESI, m/z [M, Na, calcd for C50H40N4O3CuNa: 830.2294; found: 830.2267. UV-Vis (CH2Cl2):λmax, 346, 383, 432, 592, 630 nm. IR: 2961, 2924, 1734, 1599, 1539, 1489, 1441, 1384, 1344, 1319, 1225, 1153, 1086, 1073, 1029, 1009, 995, 791, 752, 700, 502 cm -1. Cu3b: MALDI (TOF, m/z (isotope pattern, 835.4 [M, HRMS (CI, m/z [M, calcd for C52H 44N4O3Cu: 835.2704; found: 835.2710. UV-Vis (CH2Cl2, λmax, 346, 383, 432, 592, 630 nm. IR: 2960, 2922, 1734, 1599, 1540, 1508, 1489, 1441, 1318, 1233, 1225, 1152, 1091, 1074, 1040, 1009, 995, 890, 833, 791, 752, 710, 700, 502 cm-1. Cu3c: MALDI (TOF, m/z (isotope pattern, 863.4 [M, HRMS ESI
    • 2)
  • 35
    • 48449095724 scopus 로고    scopus 로고
    • 2 (3:1).
    • 2 (3:1).
  • 38
    • 48449102438 scopus 로고    scopus 로고
    • Isolation of Cu4b from CuOH: [2-Hydroxy-5,10,15,20- tetraphenylporphyrinato]Cu(II) (CuOH, 0.0145 mmol) was dissolved in p-dioxane (2 mL) and reacted with AgOTf(1 equiv) and n-butanol (b, 8 mL) under reflux for 20 h.
    • 2O (35 mL). Extraction with EtOAc (3 x 10 mL), subsequent concentration and silica gel column chromatography purification gave Cu4b in 37% yield.
    • 37% yield
  • 40
    • 48449097113 scopus 로고    scopus 로고
    • 2O (25 mL), and the green compound was extracted with EtOAc (3 x 10 mL). Cu1 was purified by silica gel column chromatography and isolated in 70% yield.
    • 2O (25 mL), and the green compound was extracted with EtOAc (3 x 10 mL). Cu1 was purified by silica gel column chromatography and isolated in 70% yield.
  • 42
    • 48449093821 scopus 로고    scopus 로고
    • Crystals suitable for X-ray diffraction studies were obtained from slow diffusion of methanol into a CH2Cl2 solution. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication data CCDC 668819 (Cu1, and CCDC 676199 (Cu3a, CCDC 676200 (Cu3d, CCDC 676201 (H3e, Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk, Crystal data for Cu1: red, 0.18 x 0.18 x 0.12 mm, C44H26N4O2Cu, M, 706.23, tetragonal, a, 15.231 (5) Å, b, 15.231 (5) Å, c, 13.452 (7) Å, α, β, γ, 90°, V, 3121 (2) Å3, T, 120 (2) K, space group I42d, Z, A, ρ
    • -3.
  • 46
    • 0002312013 scopus 로고
    • Academic Press, Inc: New York
    • Gouterman, M. The Porphyrins, Vol. III; Academic Press, Inc: New York, 1978, 1-165.
    • (1978) The Porphyrins , vol.3 , pp. 1-165
    • Gouterman, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.