1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione → Tetrahydrocurcumin

HRID 77641

반응식

HRID 77641 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:25])[CH2:11][C:12](=[O:24])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:4][C:3]=1[O:26][CH3:27]>[Pd].C(OCC)(=O)C>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:12](=[O:24])[CH2:11][C:10](=[O:25])[CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:26][CH3:27])[CH:4]=2)=[CH:16][C:17]=1[O:22][CH3:23]

참가 물질

4

반응물 1

HCID 28891,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione

생성물 1

HCID 124072Tetrahydrocurcumin수율 54%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (3a, 0.55 g, 1.5 mmol) and palladium on activated carbon (0.25 g, 5%) were combined in ethyl acetate (30 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 4 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford a solid. The crude solid was recrystallized from ethyl acetate/hexane to give 0.30 g (54%) of white crystals: mp 92-94° C. [expected mp 92-93° C.]; 1H NMR: δ 2.53 (t, 4H, J=7.9 Hz), 2.83 (m, 4H), 3.84 (s, 6H), 5.40 (s, 1H), 5.48 (s, 2H), 6.64 (m, 4H), 6.81 (d, 2H, J=8.3 Hz), 15.44 (s, 1H); 13C NMR: δ 29.2, 31.3, 40.4, 45.5, 55.9, 99.7, 110.9, 111.0, 114.3, 120.7, 132.4, 143.9, 146.3, 193.0.

후처리

  1. customfor 4 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. customthe solvent evaporated
  5. customto afford a solid
  6. customThe crude solid was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-07f700164d9b44d6a52e080f64ceccc5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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