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

HRID 1634369노트

반응식

HRID 1634369 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 suspension of Palladium-on-charcoal (10%, 2.2 g) in glacial acetic acid (15 ml) was treated with oxygen for three days. The suspension 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 crude 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 H-z,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). 13CNMR (acetone-d6) MS: m/z (+ve ion FAB in m-NBA, rel. intensity) 242.1 [100, (M)+], [, (M−SO2NH2)+]. MS: m/z (−ve ion FAB in m-NBA, rel. intensity) 394.2 [50, (M−H+NBA)−], 241.2 [100, (M−H)−]. Acc. MS (+ve ion FAB in m-NBA): m/z 242.094 C15H15O3 requires 243.1021. Found: C,; H, 4. C15H14O3 requires C, 74.36; H, 5.82%.

후처리

  1. filtrationthe solution was filtered
  2. washwashed with diglume and hot acetic acid
  3. dissolutionThe crude 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-a45901d9bf054717ba23ae7941510e90
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506792B1

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