* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Bioscience, Biotechnology and Biochemistry, 2006, vol. 70, # 6, p. 1386 - 1394
2
[ 520-26-3 ]
[ 520-33-2 ]
Yield
Reaction Conditions
Operation in experiment
65.4%
With sulfuric acid In methanol at 60℃; for 7.5 h;
General procedure: Compound 2 was synthesized by literature procedure.1 A mixture of 1 (3.5 g, 5.7 mmol) and H2SO4 (10 mL) in anhydrous CH3OH (280 mL) was stirred at 60°C for 7.5 h, ethyl acetate (1.2 L) was then added at 20°C . The solution was washed with H2O (420 mL), and dried (Na2SO4). Evaporation afforded pale-yellow powder. The crude product was dissolved in acetone (70 mL) and added dropwise (60 min) to a stirred mixture of H2O/acetic acid (150:1, 700 mL) at 95°C . The slurry was cooled to 45°C and the product filtered and dried in vacuo.
52.1%
With sulfuric acid In ethanol for 7.5 h; Reflux
Hesperidin 1.50 g (2.46 mmol) was added to 90 mL of absolute ethanol and 3 mL of concentrated sulfuric acid was added with vigorous stirring. The mixture was heated under reflux for 7.5 h.The reaction mixture was distilled off under reduced pressure. Most of the ethanol was distilled off under reduced pressure. The residue was poured into distilled water and extracted with ethyl acetate (3 x 90 mL). The extracts were combined and washed with distilled water until neutral. Ethyl acetate was distilled off, A yellow residue was obtained, and the crude product was recrystallized from ethanol / water.The yield was 52.1percent,
49%
at 20℃; for 0.166667 h;
General procedure: Sulfuric acid (2.0mL, 0.037mmol) was added dropwise to a beaker (100 mL) containing scutellarin (50 mg, 0.11 mmol). It was shaken or agitated by ultrasound agitated to dissolve the substrate in the acid at room temperature. Water (2.0 mL) was then added carefully dropwise. When the evolution of heat ceased (in 10 minutes), the mixture was added to water (15 mL) in one portion with stirring with a glass rod. The yellow crystals that were deposited were collected by suction filtration and washed by water (5 mL). In most cases, such products were pure enough for direct use. Moreover, it could be further purified by recrystallisation from aqueous methanol (70percent, v/v) or column chromatography on silica gel (eluent:ethyl acetate/formic acid/water=100/4/3, v/v/v, Rfs of SCU and SCUE were 0.1 and 0.8 on silica gel GF254 respectively). Light yellow crystals were obtained after recrystallisation (28.5mg, 93percent yield); m.p. 285–287°C (>300°C)27. IR (KBr, cm–1): νmax 3442, 3331, 3098, 1671, 1619, 1587, 1509. 1H NMR (500MHz, DMSO‑d6): δ 12.80 (s, 1H, 5‑OH), 10.48 (s, 1H, 7‑OH), 10.33 (s, 1H, 4′‑OH), 8.75 (s, 1H, 6‑OH), 7.92 (d, 2H, J=8.6Hz, C2′, C6′‑H), 6.92 (d, 2H, J=8.6Hz, C3′, C5′‑H), 6.75 (s, 1H, C3‑H), 6.58 (s, 1H, C8‑H). HR‑ESI‑MS (m/z): 309.0363 for [M+Na]+, calcd 309.0370.
0.13 mol
With sulfuric acid In dimethyl sulfoxide at 100℃; for 2 h;
0.16mol hesperidin placed in the reaction vessel,Addition of 500 mL of DMSO gave a hydrolyzate.Then dropping 50mL concentrated sulfuric acid to adjust the pH of the hydrolyzate is 5,The reaction was further stirred at 100 ° C for 2 hours under magnetic stirring,Standing filtered to give a precipitate,Drying to obtain 0.13mol hesperetin.
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 95 - 106
[2] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1200 - 1205
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7194 - 7197
[4] Patent: CN105693682, 2016, A, . Location in patent: Paragraph 0024; 0025
[5] Journal of Chemical Research, 2014, vol. 38, # 7, p. 396 - 398
[6] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 14, p. 5550 - 5557
[7] Journal of Chemical Research, 2014, vol. 38, # 7, p. 443 - 446
[8] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 107 - 117
[9] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1460 - 1465
[10] RSC Advances, 2017, vol. 7, # 84, p. 53385 - 53395
[11] Patent: CN106946835, 2017, A, . Location in patent: Paragraph 0064; 0078; 0080
[12] International Immunopharmacology, 2018, vol. 61, p. 82 - 91
3
[ 520-26-3 ]
[ 26184-96-3 ]
[ 520-33-2 ]
Reference：
[1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
[2] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 20, p. 11238 - 11243
[3] Food Chemistry, 2012, vol. 134, # 4, p. 2338 - 2344
[4] Food Chemistry, 2011, vol. 127, # 2, p. 394 - 403
[5] Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 130, p. 70 - 73
4
[ 90-33-5 ]
[ 520-26-3 ]
[ 1356391-89-3 ]
[ 520-33-2 ]
Yield
Reaction Conditions
Operation in experiment
28%
With water In dimethyl sulfoxide at 30℃; for 1 h; aq. buffer; Enzymatic reaction
α-Rhamnosyl-β-glucosidase was incubated with the aromatic alcohol 1.8 mM 4-methylumbelliferone (4-MU) as acceptor and 1.8 mM hesperidin as rutinose donor. Thin layer chromatography (TLC) of the enzymatic reaction mixture gave a weak fluorescent spot (Rf = 0.72), similar to that of 4-MU-glucoside (4-MU-Glc, Rf = 0.80). The spot was found to be a glycoconjugate that, taking into account the enzyme mechanism,10 strongly suggested the synthesis of 4-MU-rutinoside (Fig. 2). The yield of transglycosylation was 28percent after the first hour of reaction at 30 °C (Fig. 3). Subsequently, the amount of transglycosylation product remained constant for at least 3 h, while the hydrolysis was shown to proceed up to completion. This behavior is in agreement with that observed for other glycosidase-catalyzed synthesis. Transglycosylation rate is usually higher than free sugar formation rate during the first stage of the reaction and, later on, transglycosylation product concentration reaches a plateau or diminishes because it acts as a substrate of the enzyme. [24] and [25] The increment of the reaction temperature up to the near-optimal for hydrolysis (60 °C) was shown to diminish the yield of 4-MU-rutinoside, probably by favoring the hydrolysis of the transglycosylation product. The highest yield was obtained for the acceptor donor ratio in the range 0.8-1:1 (data not shown).
Reference：
[1] Journal of the Chemical Society, 1956, p. 632,634
[2] Journal of the Chemical Society, 1956, p. 632,634
[3] Nippon Kagaku Zasshi, 1958, vol. 79, p. 709,717[4] Chem. Zentralbl., 1959, vol. 130, p. 6808
General procedure: Apigenin: A solution of naringenin (5.0 g, 18 mmol) and iodine (5.0 g,19 mmol) in pyridine (50 mL) was heated to 95 C for 5 h. The mixturewas poured into ice water. The resulting precipitate was filtered,and then washed with water, dilute hydrochloric acid and saturatedsodium thiosulfate. Recrystallisation of the dried residue from ethanolafforded apigenin: 3.20 g; 66%
Acetic acid (2S,3S,4R,5S,6R)-3-acetoxy-6-[(S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-2-methyl-5-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester[ No CAS ]
hexa-O-acetyl-2-O-β-L-fucopyranosyl-α-D-galactopyranosyl bromide[ No CAS ]
[ 520-33-2 ]
Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester[ No CAS ]
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester[ No CAS ]
Specifically preferred are compounds selected the group of: ... 3-OH-Flavone Fisetin, Myricetin, Flavanone, Hesperetin, Daidzein, Genistein, Genistin, ...
(iii) one or more additional aroma substances including their physiologically tolerated salts, whereby at least one of these aroma substances is a sweetness intensifying aroma substance and is selected from the group comprising hesperetin 4-hydroxydihydrochalcone, and propenylphenylglycoside (chavicol glycoside)
Particular preference is given to combinations comprising as biological control agent an isoflavone selected from the group consisting of [Group (3)]: (3.3) formononetin, (3.6) hesperetin, (3.7) naringenin,
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 60℃; for 2.5h;Inert atmosphere;
General procedure: Naringenin (174 mg, 0.62 mmol), WSCHCl (79 mg, 0.42 mmol), and a small amount of N,N-dimethylaminopyridine (DMAP) were added to a solution of PJ-1 succinate ester (180 mg, 0.32 mmol) in tetrahydrofuran (2.0 mL), and stirred at 60 C for 2.5 h under a nitrogen atmosphere. A small amount of distilled water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and condensed in vacuo to give an amorphous powder, which was purified by silica gel column chromatography (n-hexane : AcOEt = 5/1-4/1), followed by HPLC (n-hexane : AcOEt = 2/1) to afford compound 1 (133.6 mg, 51%) as a colorless powder.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 60℃; for 2.5h;Inert atmosphere;
General procedure: Naringenin (174 mg, 0.62 mmol), WSCHCl (79 mg, 0.42 mmol), and a small amount of N,N-dimethylaminopyridine (DMAP) were added to a solution of PJ-1 succinate ester (180 mg, 0.32 mmol) in tetrahydrofuran (2.0 mL), and stirred at 60 C for 2.5 h under a nitrogen atmosphere. A small amount of distilled water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and condensed in vacuo to give an amorphous powder, which was purified by silica gel column chromatography (n-hexane : AcOEt = 5/1-4/1), followed by HPLC (n-hexane : AcOEt = 2/1) to afford compound 1 (133.6 mg, 51%) as a colorless powder.
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Alkaline conditions;
General procedure: K2CO3 (172.76 mg, 1.25 mmol) and the appropriate substitutedbromine (4-10 mmol) were added, under stirring, to a solution of <strong>[520-33-2]hesperetin</strong>(604 mg, 2 mmol) in anhydrous DMF (15 mL). Another 1 mmolof K2CO3 was intermittently added to the solution to keep the pH as aweak alkaline. The mixture was reacted at room temperature for 4-6 hunder atmospheric conditions. The progress of the reaction was monitoredby TLC. The reaction mixture poured into ice cold water thenacidified by dilute hydrochloric acid and extracted with ethyl acetate,then washed three times with saturated aqueous NaCl solution. After drying with anhydrous sodium sulfate, the solution was filtered throughabsorbent cotton. The precipitate obtained by removing the solventunder reduced pressure was purified by column chromatography (SiO2)using trichloromethane/petroleum ether (1:1-5) as eluent. The purifiedprecipitate was recrystallized from dichloromethane/petroleum ether.
70.1%
With potassium carbonate; In acetone; at 56℃; for 10.5h;
Compound 3 was synthesized by literature method.2 A mixture of 2 (1.0 g , 3.31 mmol), dry K2CO3 (2.4 g, 17.4 mmol) and benzyl bromide (1.2 mL), were dissolved in dry acetone (70 mL) and refluxed at 56C for 7.5 h. Then compound 2 (0.2 g, 0.662 mmol) and dry K2CO3 (1.2 g , 8.7 mmol) continued to be added and reacted at 56C for 3h. The slurry was cooled to 45C and dried in vacuo. The crude product was purified by a silica-gel column (petroleum ether/ethyl acetate, 10:1) to obtain compound 3 as a yellow powder.
General procedure: For synthesis of ester derivatives, compound 2 was stirred at 0-5 C for 3-7 h with different substituted acyl chlorides in the presence of trienthylamine and dry acetone. Reaction mixture was filtered and solvent was removed under reduced pressure. The purity of the compounds was obtained by column chromatography using silica gel as stationary phase, and petroleum ether/ethyl acetate (20:1) as mobile phase.
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochroman-7-yl propionate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
24.12%
With triethylamine; In acetone; at 0 - 5℃;
General procedure: For synthesis of ester derivatives, compound 2 was stirred at 0-5 C for 3-7 h with different substituted acyl chlorides in the presence of trienthylamine and dry acetone. Reaction mixture was filtered and solvent was removed under reduced pressure. The purity of the compounds was obtained by column chromatography using silica gel as stationary phase, and petroleum ether/ethyl acetate (20:1) as mobile phase.
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochroman-7-yl benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18.8%
With triethylamine; In acetone; at 0 - 5℃;
General procedure: For synthesis of ester derivatives, compound 2 was stirred at 0-5 C for 3-7 h with different substituted acyl chlorides in the presence of trienthylamine and dry acetone. Reaction mixture was filtered and solvent was removed under reduced pressure. The purity of the compounds was obtained by column chromatography using silica gel as stationary phase, and petroleum ether/ethyl acetate (20:1) as mobile phase.
With triethylamine; at 20℃; for 0.166667h;Inert atmosphere;
General procedure: A flame-dried round-bottom flask was charged under argon with <strong>[520-33-2]hesperetin</strong> (1 equiv.) and acetone. To this solution, freshly distilled triethylamine (2 equiv.) was then added under argon. After the solution was stirred for 10min at room temperature, the corresponding acid chloride (1.2-2.4 equiv.) was added quickly. The reaction mixture was stirred for 10min at the same temperature and quenched with distilled water. This aqueous mixture was extracted with CH2Cl2, and combined organic extracts were dried over anhydrous MgSO4. After removal of the solvent, the crude product was purified by flash column chromatography to get the desired products. The synthetic process is summarized in Scheme 1 . All derivatives except K-1b are novel.
General procedure: Specifically, a thermally dried round bottom flask under argon atmosphere was charged with hessperin (1 eq) and acetone. To the solution, freshly distilled triethylamine (2 eq.) Was added under an argon atmosphere. The solution was stirred at room temperature for 10 minutes and then the corresponding acid chloride (R-C (= O) Cl or R'-C (= O) Cl; 1.2-2.4 equivalents) was added rapidly. The reaction mixture was stirred at the same temperature for 10 minutes and then quenched with distilled water. The aqueous mixture was extracted with CH2Cl2 and the organic extracts were collected and dried over anhydrous MgSO4. After removal of the solvent, the crude product was purified by flash column chromatography to give the desired product
With potassium carbonate; In acetone; at 60 - 65℃; for 12h;Inert atmosphere;
A solution of <strong>[520-33-2]hesperetin</strong> (3.02 g, 10 mmol) and anhydrous K2CO3 (11.04 g, 80 mmol) in (CH3)2SO4 (2.9 mL, 30 mmol), the mixture was stirred under nitrogen for 12 h at 60-65 C. The resulting precipitate was filtered and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and the solution was washed with saturated salt water (30 mL × 3). The organic phase was dried over anhydrous MgSO4 and chromatographed on silica gel using petroleum ether/ethylacetate (10 : 1) as eluent to afford a light yellow solid 2.1 g (61%), m.p.149-150 C (lit.16 m.p. 149-151 C);
With sulfuric acid; In methanol; water; for 6h;Reflux;
General procedure: Compounds 12-14 which had been isolated from the ethyl acetate fraction were subjected to acid hydrolysis by dissolving about 5 mg of each compound in 5 mL methanol and refluxing with 20 mL aqueous H2SO4 (50%) for 6 h. The reaction mixtures were extracted twice with chloroform (50 mL). The organic layers were collected, concentrated and crystallised to yield the corresponding aglycones. The aqueous hydrolysed was spotted on paper chromatography plates together with authentic sugars (PC, ethyl acetate-formic acid-acetic acid-water, 10:1.1:1.1:2.6, v/v).
With flavonol 7-O-rhamnosyltransferase from Arabidopsis thaliana; In dimethyl sulfoxide; at 20℃; for 48h;Microbiological reaction; Enzymatic reaction;
General procedure: Cultures were made to a volume of 200 mL in LB medium supplemented with respective antibiotics. In case of recombinant strain harboring pET41b-AtUGT89C1 kanamycin 50 mug/mL was added inculture broth while in recombinant strain harboring pET32b-AtRHM1, ampicillin 100 mug/mL was added. After 3 hours, each culture was aseptically transferred into 50 mL falcon tube and centrifuged for 10 min at 1000 RCF. Supernatant was discarded and cell was re-suspended in autoclaved distilled water. Equal density (OD6001.5) of cells was inoculated into 100 mL LB medium in shake flask at 4 RCF and incubated at 37C until the final OD600 reached to 0.5-0.7. The cultures were then induced by 0.1 mM isopropyl-1-thio-beta-D-galactopyranoside (IPTG) and incubated at 20C for 15 h to allow protein expression. Flavonoids as substrates were added at a concentration of 0.2 mM by dissolving in dimethyl sulfoxide (DMSO) in each flask for whole-cell biocatalysis reaction. The biotransformation reaction was carried out for 48 h at 20C.
General procedure: The copper(II) complexes were obtained by adding asolution of copper(II) perchlorate to a solution of thedesired flavonoid both in methanol under stirring.After 30-40 min, a methanol solution of 1,10-phenanthrolinewas added in 1:1:1 molar ratio. The reactionmixture was kept under reflux for eight hours. Theobtained solids were washed with methanol and etherand then dried in vaccuo. [Cu(H2O)2(L1)(phen)](ClO4) (1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).3a: Yellow solid, 47% yield, mp: 101-105C. IR (KBr) cm-1: 3423 (nuOH); 2956, 2837 (nuCH3, nuCH2); 1645 (nuC=O); 1553, 1512, 1462 (nuc=c Ar); 1H NMR (300MHz, CDCl3): delta 12.51 (s, 1H, OH), 6.86-7.03 (m, 3H, ArH), 5.94 (s, 1H, ArH), 5.29 (dd, J=12.9, 2.8Hz, 1H, H-2), 3.91 (s, 3H, O-CH3), 3.89 (s, 2H, N-CH2-Ar), 3.03 (dd, J=17.1, 12.9Hz, 1H, cis-H-3), 2.76 (m, 4H, 2×N-CH2), 1.17 (m, 6H, 2×CH3). HR-MS: m/z [M+H]+ calcd for C21H26NO6: 388.1755; found 388.1755.
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
6-[4-(2-morpholin-4-ylethyl)piperazine-1-yl]methyl-3',5,7-trihydroxyflavanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
In methanol; water; for 0.5h;
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).
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