Isoxanthohumol → Sophoraflavanone B

HRID 564215

반응식

HRID 564215 반응식
[CH3:1][C:2]([CH3:26])=[CH:3][CH2:4][C:5]1[C:6]([OH:25])=[CH:7][C:8]([O:23]C)=[C:9]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[O:11][C:10]=12>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3].C1COCC1>[CH3:1][C:2]([CH3:26])=[CH:3][CH2:4][C:5]1[C:10]2[O:11][C@H:12]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[CH2:13][C:14](=[O:15])[C:9]=2[C:8]([OH:23])=[CH:7][C:6]=1[OH:25]

참가 물질

4

반응물 1

HCID 513197Isoxanthohumol

생성물 1

HCID 480764Sophoraflavanone B수율 92.3%

시약·촉매·용매 2

HCID 2734571Scandium(III) triflate촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of isoxanthohumol (50 mg, 0.14 mmol), KI (34 mg, 0.21 mmol) and Sc(OTf)3 (105 mg, 0.21 mmol), 10 ml of THF are added and the solution is heated for 2.5 h under reflux. The mixture is stirred overnight at room temperature and concentrated in vacuum. The scandium salt is separated off via a short silica gel column (eluted with CHCl3/methanol=100:1). The resultant solution is concentrated to dryness in vacuum, the residue is taken up in CHCl3 and eluted through a silica gel column using CHCl3/-methanol=100:1. 8-Prenylnaringenin (formula (III) where R1=prenyl, R2=H) (44 mg, 92%) is obtained as a light-yellowish solid.

후처리

  1. additionare added
  2. temperaturethe solution is heated for 2.5 h
  3. temperatureunder reflux
  4. concentrationconcentrated in vacuum
  5. customThe scandium salt is separated off via a short silica gel column (eluted with CHCl3/methanol=100:1)
  6. concentrationThe resultant solution is concentrated to dryness in vacuum
  7. washeluted through a silica gel column

출처 및 근거

ORD 기록
ord-4784225c6fc94740bca3df471d39b4d1
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067622B2

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