Water → [6]-Dehydroshogaol

HRID 918999

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HRID 918999 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)=[O:9].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O>O1CCCC1>[OH:18][C:15]1[CH:16]=[CH:17][C:12](/[CH:11]=[CH:10]/[C:8](=[O:9])/[CH:7]=[CH:6]/[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:13][C:14]=1[O:19][CH3:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5281794Shogaol

생성물 1

HCID 102316888[6]-Dehydroshogaol수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

[6]-Shogaol (276 mg, 1.0 mmol) was dissolved in tetrahydrofuran (THF) and cooled down to 0° C. To this mixture, a solution of DDQ (181 mg, 0.8 mmol) in THF was added. The mixture was stirred at 0° C. for 30 minutes and then warmed to room temperature (RT) for 3 hours. Then water was added and the resulting mixture was extracted with EtOAc (×3). The organic phase was washed with water (×1) and brine (×1), dried over anhydrous NaSO4, and filtered. The filtration was evaporated and the residue was purified by chromatography column (CC) (hexane/ethyl acetate=8:1 and 6:1) to give the desired compound as a yellow oil (170 mg, yield: 62%); 1H NMR (600 MHz, CDCl3) δ 7.59 (1H, d, J=15.9 Hz, H-1), 6.82 (1H, d, J=15.9 Hz, H-2), 6.44 (1H, d, J=15.6 Hz, H-4), 6.99 (1H, dt, J=15.6, 7.0 Hz, H-5), 2.27 (2H, q, J=7.0 Hz, H-6), 1.51 (2H, m, H-7), 1.34-1.29 (4H, m, H-8 and H-9), 0.90 (3H, t, J=6.8 Hz, H-10), 7.07 (1H, d, J=1.4 Hz, H-2′), 6.93 (1H, d, J=8.2 Hz, H-5′), 7.14 (1H, dd, J=8.2, 1.4 Hz, H-6′), and 3.93 (3H, s, OMe-3′); 13C NMR (150 MHz, CDCl3) δ 143.3 (d, C-1), 123.3 (d, C-2), 189.3 (s, C-3, C═O), 129.1 (d, C-4), 148.0 (d, C-5), 32.7 (t, C-6), 27.9 (t, C-7), 31.4 (t, C-8), 22.4 (t, C-9), 14.0 (q, C-10), 127.4 (s, C-1′), 109.7 (d, C-2′), 148.1 (s, C-3′), 146.8 (s, C-4′), 114.8 (d, C-5′), 122.9 (d, C-6′), and 56.0 (q, OMe-3′); positive ESI-MS, m/z 275 [M+H]+.

후처리

  1. temperaturewarmed to room temperature (RT) for 3 hours
  2. extractionthe resulting mixture was extracted with EtOAc (×3)
  3. washThe organic phase was washed with water (×1) and brine (×1)
  4. dry with materialdried over anhydrous NaSO4
  5. filtrationfiltered
  6. filtrationThe filtration
  7. customwas evaporated
  8. customthe residue was purified by chromatography column (CC) (hexane/ethyl acetate=8:1 and 6:1)

출처 및 근거

ORD 기록
ord-4c16b33c9a934e709d9a8e017d067a36
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272994B1

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