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

HRID 1634369ノート

反応式

HRID 1634369 の反応式
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

参加物

5

反応物 2

HCID 977OxygenHCID 5281708Daidzein

生成物 1

HCID 3829754',7-Dihydroxy-3,4-dihydroisoflavone収率 75.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-a45901d9bf054717ba23ae7941510e90
出典データセット
uspto-grants-2003_01
特許番号
US06506792B1

反応ノート

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