Oxygen → 4',7-Dihydroxy-3,4-dihydroisoflavone

HRID 1247493노트

반응식

HRID 1247493 반응식
O=O.[OH:3][C:4]1[CH:21]=[CH:20][C:7]([C:8]2[C:17](=O)[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][CH:9]=2)=[CH:6][CH:5]=1>C(O)(=O)C.[Pd]>[OH:19][C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][CH:8]([C:7]3[CH:20]=[CH:21][C:4]([OH:3])=[CH:5][CH:6]=3)[CH2:9][O:10]2)=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 977OxygenHCID 5281708Daidzein

생성물 1

HCID 3829754',7-Dihydroxy-3,4-dihydroisoflavone수율 75.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

A suspention of Palladium-on-charcoal (10%, 2.2 g) in glacial acetic acid (15 ml) was treated with oxygen for three days. The suspention catalyst was added to the solution of 4′,7-dihydroxy isoflavone (0.5 g, mmol) in diglume (60 ml). After 30 min. of catalytic hydrogenation at atmospheric pressure, the solution was filtered and washed with diglume and hot acetic acid. The combined filtrate were evaporoted by using water vacuum pump followed by high vacuum pump. The curde was dissolved in ethylacetate and wished with sodium bicarbonate (5%) and with water till neutral, dried (MgSO4) filtred and evaporeted to give pale white crude (0.385 g) which was recrystallized in aquoes ethanol to give 22a as white crystals (0.361 g), m.p. 156–158° C. (lit. 158° C.). Rfs=IR (KBr) 3380−2720 cm−1. δH (acetone-d6) 2.89 (2H, m, C-4-H2), 3.1 (1H, m, C-3-H), 3.94 (1H, t, J=10.38 Hz, C-2-HA), 4.18 (1H, m, C-2-HE), 6.29 (1H, d, JC-8-H & C-6-H=2.44 Hz, C-8-H), 6.37 (1H, dd, JC-6-H & C-7-H=8.24 Hz, JC-6-H & C-8-H=2.44 Hz, C-6-H), 6.82 (2H, dd, JC-3′-H & C-2′-H=8.55 Hz, JC-3′ & C-5-H=2.74 Hz, C-3′-H and C-5′-H or C-2′-H and C-6′-H), 6.89 (1H, d, JC-5-H & C-6-H=8.24 Hz, C-5-H), 7.16 (2H, dd, JC-2′-H & C-5′-H=8.24 Hz, JC-2′-H & C-6′-H=2.74 Hz, C-2′-H and C-6′-H or C-3′-H and C-5′-H), 8.15 (1H, br s, C-7-OH or C-4′-OH) and 828 (1H, br s, C-4′-OH or C-7-OH).

후처리

  1. filtrationthe solution was filtered
  2. washwashed with diglume and hot acetic acid
  3. dissolutionThe curde was dissolved in ethylacetate
  4. dry with materialdried (MgSO4)
  5. customto give pale white crude (0.385 g) which
  6. customwas recrystallized in aquoes ethanol

출처 및 근거

ORD 기록
ord-31d0f3fa1da447f99bc48d5fa05ff47b
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129269B2

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