Isoxanthohumol → Sophoraflavanone B

HRID 564215

反応式

HRID 564215 の反応式
[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]

参加物

4

反応物 1

HCID 513197Isoxanthohumol

生成物 1

HCID 480764Sophoraflavanone B収率 92.3%

試薬・触媒・溶媒 2

HCID 2734571Scandium(III) triflate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4784225c6fc94740bca3df471d39b4d1
出典データセット
uspto-grants-2011_11
特許番号
US08067622B2

関連ノート

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