반응 #90866

반응 방정식

Mono-Propargyl Curcumin

2-(2-(2-azidoethoxy)ethoxy)ethanol

sodium ascorbate

→

Mono-2-(2-(2-(4-(methylene)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethanol-curcumin

수율 26.0%

용매

tBuOH

CHCl3

H2O

반응 조건

후처리

1. 1
   기타was removed under vacuum
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in CHCl3
3. 3
   세척washed with H2O
4. 4
   기타the organic phase was separated
5. 5
   건조dried over Na2SO4
6. 6
   기타evaporated
7. 7
   기타Purification
8. 8
   세척eluting with CH2Cl2—CH2Cl2

실험 절차

To a stirred solution of Mono-Propargyl Curcumin 5 (63 mg, 0.16 mmol) and 2-(2-(2-azidoethoxy)ethoxy)ethanol (46 mg, 0.26 mmol) in tBuOH (1.1 mL) and CHCl3 (0.3 mL) was added a prepared solution of Cu(OAc)2 (8 mg, 0.03 mmol) and sodium ascorbate (13 mg, 0.07 mmol) in H2O (1.3 mL). After vigorous stirring overnight the solvent was removed under vacuum. The mixture was dissolved in CHCl3, washed with H2O and the organic phase was separated, dried over Na2SO4 and evaporated. Purification was performed by column chromatography, eluting with CH2Cl2—CH2Cl2: MeOH 98:2. Yield 26%. NMR 1H (CDCl3), δ (ppm): 3.55-3.60 (m, 8H); 3.72-3.72 (t, 3H); 3.87-3.94 (m, 8H); 4.54-4.55 (t, 2H); 5.80 (s, 1H); 6.07 (s, 1H); 6.46-6.50 (dd, 2H); 6.92-6.94 (d, 1H); 7.05-7.12 (m, 5H); 7.56-7.60 (q, 2H); 7.92 (s, 1H).). MS (ESI) calcd. for C30H35N3O9: 581.61. found: 582.3 [M+H]+, 604.3 [M++Na], 620.3 [M++K].

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