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Chemistry
Heterocyclic Building Blocks
Pyrans
5,7-Dimethoxyflavone
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[ CAS No. 21392-57-4 ] {[proInfo.proName]}

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Product Details of [ 21392-57-4 ]

CAS No. :21392-57-4 MDL No. :MFCD00016943
Formula : C17H14O4 Boiling Point : -
Linear Structure Formula :- InChI Key :JRFZSUMZAUHNSL-UHFFFAOYSA-N
M.W : 282.29 Pubchem ID :88881
Synonyms :

Safety of [ 21392-57-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21392-57-4 ]

* 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.

  • Downstream synthetic route of [ 21392-57-4 ]

[ 21392-57-4 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 480-40-0 ]
  • [ 77-78-1 ]
  • [ 21392-57-4 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In acetone at 60℃; for 6h;
97% With potassium carbonate In acetone at 60℃; for 6h; 1 Preparation of 5,7-dimethoxyflavone Chrysin (lg, 3.94 mmol) and potassium carbonate (1.63 g, 11.8 mmol) were dissolved in 30 mL of acetone, and dimethyl sulfate (1.99 g, 15.8 mmol) was added at room temperature, and refluxed at 60 ° C for 6 hours. After the TLC monitoring reaction was completed, the reaction was quenched with aqueous ammonia (5 mL of 10% sol in water) and acetone was removed under reduced pressure. Filter, filter cake washed with water and dried. Recrystallization from ethyl acetate gave 5,7-dimethoxyflavone (1.08 g), yellow crystals, yield 97%.
95% With potassium carbonate In acetone at 60℃; for 12h;
58% With potassium carbonate In acetone for 24h; Reflux; Synthesis of flavone derivatives5,7-Dimethoxyflavone (4) (Do et al., 2009) A mixture of chrysin (510 mg, 2 mmol) in 20 mL of anhydrous acetone, anhydrouspotassium carbonate and dimethyl sulfate were added slowly under stirring. Thereaction mixture was refluxed for 24 h. Potassium carbonate was removed by suctionfiltration. The filtrate was evaporated and purified by column chromatography to obtainthe target molecule as yellow solid 327 mg (58 %).
55% With potassium carbonate In N,N-dimethyl-formamide for 4.5h; Heating;
With water Versetzen mit Natronlauge;
With sodium hydroxide; acetone
With potassium carbonate; acetone
With potassium carbonate
With potassium carbonate In acetone for 8h;
With potassium carbonate In acetone Reflux;

Reference： [1]Location in patent: experimental part Righi, Giuliana; Antonioletti, Roberto; Silvestri, Ilaria Proietti; D'Antona, Nicola; Lambusta, Daniela; Bovicelli, Paolo [Tetrahedron, 2010, vol. 66, # 6, p. 1294 - 1298]
[2]Current Patent Assignee: Jing Linlin; Ma Huiping; Fan Pengcheng; Fan Xiaofei; He Lei; Jia Zhengping - CN104926768, 2018, B Location in patent: Paragraph 0024-0026
[3]Location in patent: experimental part Lee, Hyo Seon; Park, Kwang-Su; Lee, Bokhui; Kim, Dong-Eun; Chong, Youhoon [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 21, p. 7331 - 7337]
[4]Kingkaew, Krongkan; Ruga, Ritbey; Chavasiri, Warinthorn [Chemistry Letters, 2018, vol. 47, # 3, p. 258 - 261]
[5]Briggs, Malcolm T.; Duncan, Graham L. S.; Thornber, Craig W. [Journal of Chemical Research, Miniprint, 1982, # 9, p. 2461 - 2487]
[6]Tasaki [Acta Phytochimica, 1924, vol. 2, p. 127][Acta Phytochimica, 1927, vol. 3, p. 14][Chemisches Zentralblatt, 1926, vol. 97, # I, p. 956]
[7]Gulati; Venkataraman [Journal of the Chemical Society, 1936, p. 267]
[8]Murti et al. [Proceedings - Indian Academy of Sciences, Section A, 1948, # 27, p. 33,35]
[9]Joseph-Nathan, P.; Abramo-Bruno, D.; Torres, Ma. A. [Phytochemistry, 1981, vol. 20, p. 313 - 318]
[10]Chauhan, J. S.; Kumar, Santosh; Chaturvedi, Rajesh [Phytochemistry, 1984, vol. 23, # 10, p. 2404 - 2405]
[11]Choi, Yong-Sung; Kim, Yoon-Jung; Lee, Ju Yeun; Lee, Jinu; Jeong, Jin-Hyun [Heterocycles, 2014, vol. 89, # 12, p. 2794 - 2805]
  • 2
  • [ 480-40-0 ]
  • [ 520-28-5 ]
  • [ 21392-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 42% With potassium carbonate In tetrahydrofuran
Reference： [1]Shin, Joon-Su; Kim, Kyoung-Soon; Kim, Myoung-Bohm; Jeong, Jae-Hoon; Kim, Bak-Kwang [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 6, p. 869 - 874]
  • 3
  • [ 480-40-0 ]
  • [ 74-88-4 ]
  • [ 21392-57-4 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate
90% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; 5,7-Dimethoxyflavone (26) To a stirred solution ofchrysin (254 mg, 1.0 mmol) in dry DMF (5 mL) was added K2CO3(414 mg, 3.0 mmol) and CH3I (426 mg, 3.0 mmol). After the addition,the mixture was stirred for 15 h at room temperature. The reaction mixture wasthen diluted with CH2Cl2 (20 mL) and poured into aqueousHCl (0.1 M) (10 mL). The organic layer was separated, washed with H2O(3×10 mL) and dried over Mg2SO4. After concentrated todryness under reduced pressure, the crude product was purified by columnchromatography on silica (petroleum ether/ethyl acetate 1:1) to afford theknown compound 268 (253 mg, 90%) as a whitesolid.
90% With potassium carbonate In acetone at 60℃; 2 Taking the 7, 8 - dihydroxy flavone (III) 400 mg in round-bottom flask, add 1.5 g K2CO3, Add 50 ml anhydrous acetone dissolved, add 500 μl iodo methane, 60 °C reflux overnight. Reaction finishes, and steaming and removing acetone, adding water - ethyl acetate extraction, the organic phase pressurized steam to dryness to obtain a yellow solid compound (yield 90%) IV.
With potassium carbonate
With potassium carbonate In acetone at 60℃; General procedure (GP2) for the preparation of methylated flavones and isoflavones 15-19 General procedure: Methyl iodide (25 mmol, 5 eq) was added to a solution of potassium carbonate (30 mmol, 6 eq) and flavones (5mmol, 1.0 equal) or isoflavones (5 mmol, 1.0 equal) in acetone (60 mL). The reaction mixture was stirred overnight at 60°C, and the solvent was then evaporated in vacuum. The residue was purified by silica gel column chromatography, eluting with a solution of 15% MeOH in dichloromethane (Scheme S2), to yield yellow solid 15-19
With potassium carbonate In dichloromethane at 20℃;

Reference： [1]Wang, Cai-Ling; Zheng, Xing; Meng, Wei-Dong; Li, Hong-Qi; Qing, Feng-Ling [Tetrahedron Letters, 2005, vol. 46, # 32, p. 5399 - 5402]
[2]Lu, Kui; Chu, Jie; Wang, Haomeng; Fu, Xiaoli; Quan, Dewu; Ding, Hongxia; Yao, Qingwei; Yu, Peng [Tetrahedron Letters, 2013, vol. 54, # 47, p. 6345 - 6348]
[3]Current Patent Assignee: SHANDONG UNIVERSITY - CN107987020, 2018, A Location in patent: Paragraph 0036; 0037; 0038
[4]Zheng, Xing; Meng, Wei-Dong; Xu, Yang-Yan; Cao, Jian-Guo; Qing, Feng-Ling [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 5, p. 881 - 884] Wang, Cai-Ling; Li, Hong-Qi; Meng, Wei-Dong; Qing, Feng-Ling [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4456 - 4458]
[5]Cui, Chang-Yi; Liu, Jun; Zheng, Hong-Bo; Jin, Xue-Yang; Zhao, Xiao-Yu; Chang, Wen-Qiang; Sun, Bin; Lou, Hong-Xiang [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1545 - 1549]
[6]Huang, Shenzhen; Wang, Xiang; Lin, Guifeng; Cheng, Jie; Chen, Xiuli; Sun, Weining; Xiang, Rong; Yu, Yamei; Li, Linli; Yang, Shengyong [RSC Advances, 2019, vol. 9, # 16, p. 9323 - 9330]
  • 4
  • [ 21392-57-4 ]
  • [ 480-40-0 ]
YieldReaction ConditionsOperation in experiment
90% With boron tribromide In dichloromethane at 20℃; for 20h; Inert atmosphere;
89% Stage #1: Dimethyl-chrysin With boron tribromide In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With methanol Inert atmosphere;
86% With pyridine hydrochloride at 180℃; for 6h; Inert atmosphere; Chrysin (1): The mixture of the compound 6 (1.4 g, 0.005 mol) and excess pyridine hydrochloride (5.0 g) was heated at 180 °C for 6 h under an N2 atmosphere. Then the mixture was cooled to room temperature and H2O (100 mL) was added. The mixture was stirred for another 30 min and cooled to approximately 5 °C for several hours. The precipitate was filtered off, washed with cold ethanol and recrystallised from absolute ethanol to give a light yellow powdery (1.1 g, yield 86%);m.p. 280-284 °C (lit.16 282-285 °C); IR, ν/cm-1: 3410 (OH) 1654 (C=O);1H NMR (400 MHz, DMSO-d6), δ 6.23 (d, 1H, J = 2.0 Hz, H-6), 6.53(d, 1H, J = 2.0 Hz, H-8), 6.97 (s, 1H, H-3), 7.55-7.62 (m, 3H, H-4′,5′,6′),8.06 (m, 2H, H-2′,3′), 10.94 (s, 1H, OH-7),12.83 (s, 1H, OH-5). MS (m/z):255 [M + 1]+.
85% With pyridine hydrochloride at 180℃; for 5h; Inert atmosphere; Chrysin (1) A mixture of compound 5 (1.4 g, 5 mmol) and excess pyridine hydrochloride (5.0 g) was heated at 180 °C for 5 h under N2 atmosphere. Then the mixture was cooled to room temperature and H2O (100 mL) was added. The mixture was stirred for another 30 min and cooled to approximately 5 °C for several hours. The precipitate wasfiltered off, washed with cold ethanol and recrystallised from absolute ethanol to give a light yellow powder (1.1 g, yield 85%); m.p. 282-283°C (lit.28 282-285 °C); IR νmax (KBr/cm-1): 3386 (OH), 1623 (C=O);1H NMR (500 MHz, DMSO-d6), δ 6.23 (d, 1H, J = 2.0 Hz, H-6), 6.53(d, 1H, J = 2.0 Hz, H-8), 6.98 (s, 1H, H-3), 7.58-7.62 (m, 3H, H-4′,5′,6′),8.07-8.08 (m, 2H, H-2′,3′), 10.96 (s, 1H, OH-7),12.83 (s, 1H, OH-5); MS(m/z): 255 [M+H]+.
82% With boron tribromide In dichloromethane for 12h; Inert atmosphere; Reflux; 3.1 Synthesis Example 3: General procedure for demethylation General procedure: To the 5a-5b flavone solution in anhydrous dichloromethane, 3 boron bromide (5 equivalents) per methoxy functional group was added at 0° C. under an argon atmosphere, and the reaction mixture was stirred under reflux for 12 hours. After cooling to room temperature, the reaction mixture was quenched with ice water and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, the aqueous layer was adjusted to pH 7 and extracted with ethyl acetate. The organic layer was collected, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain demethylated compounds 6a to 6d.
71.5% With pyridine; hydrogenchloride at 220℃; for 0.5h; 5,7-Dihydroxy-2-phenyl-4H-chromen-4-one (6): yellow powder This compound was prepared from a mixture of 5 (1 g, 3.3 mmol) and pyridine HCl (10 g, 86.9 mmol) and was warmed to 220 °C for 30 min, and then, the mixture was cooled to RT, acidified with 5 % HCl (200 ml), and followed by extraction with EtOAc (250 9 2 ml). The organic phase was dried (MgSO4) for 15 min, and the mixture was filtered and evaporated. The residue was purified by column chromatography (petroleum ether/EtOAc) to give 6 as yellow powder; yield: 71.5 %; IR (KBr) νmax 3,450 (OH), 3,350 (OH), 1,652 (C=O) cm-1; 1HNMR (DMSO-d6, 400 MHz): δ = 12.01 (1H, s, OH),11.49 (1H, s, OH), 7.82-7.92 (2H, d, J = 7.67 Hz, H-20,60), 7.44-7.58 (3H, t, J = 7. 45 Hz, H-30, 40, 50), 6.64 (1H, s, H-8), 6.44 (1H, s, H-3), 6.24 (1H, s, H-6); 13C NMR(DMSO-d6, 100 MHz): δ = 181.6(C, C-4, C=O), 164.3(C,C-7), 163.0(C, C-5), 161.5(C, C-2), 157.3 (C, C-9), 132.3(C, C-10), 131.6 (C, C-40), 130.3(CH, C-30, C-50), 128.8(CH, C-20, C-60), 104.1(C, C-10), 105.0(CH, C-3),99.0(CH, C-6), 94.0(CH, C-8); ESI-MS: m/z 255.06[M+H]+. Anal. Calcd. for C15H10O4 (254.24) C, 70.86; H,3.96. Found: C, 70.45; H, 4.0.
68% With pyridine hydrochloride at 220℃; for 0.25h;
66% With N-butyl-N-methylimidazolium heptachlorodialuminate In dichloromethane at 40℃; for 4h;
With boron tribromide In dichloromethane Heating;

Reference： [1]Mokar, Bhanudas Dattatray; Yi, Chae S. [Organometallics, 2019, vol. 38, # 24, p. 4625 - 4632]
[2]Basílio, Nuno; Lima, João Carlos; Cruz, Luís; de Freitas, Victor; Pina, Fernando; Ando, Hiroki; Kimura, Yuki; Oyama, Kin-Ichi; Yoshida, Kumi [European Journal of Organic Chemistry, 2017, vol. 2017, # 37, p. 5617 - 5626]
[3]Liu, Man; Zhang, Ji; Yang, Jian; Yang, Bo; Cui, Wei [Journal of Chemical Research, 2014, vol. 38, # 3, p. 134 - 136]
[4]Wang, Qian; Cui, Wei; Yang, Jian; Yang, Bo [Journal of Chemical Research, 2015, vol. 39, # 5, p. 300 - 302]
[5]Current Patent Assignee: KOREA UNIVERSITY - KR2020/112201, 2020, A Location in patent: Paragraph 0130-0137
[6]Khanapur, Manjulatha; Pinna, Nishal K.; Badiger, Jaishree [Medicinal Chemistry Research, 2015, vol. 24, # 6, p. 2656 - 2669]
[7]Location in patent: experimental part Hu, Kun; Wang, Wei; Cheng, Hong; Pan, ShaSha; Ren, Jie [Medicinal Chemistry Research, 2011, vol. 20, # 7, p. 838 - 846]
[8]Liu, Tao; Hu, Yongzhou [Synthetic Communications, 2004, vol. 34, # 17, p. 3209 - 3218]
[9]Ravishankar, Divyashree; Watson, Kimberly A.; Greco, Francesca; Osborn, Helen M. I. [RSC Advances, 2016, vol. 6, # 69, p. 64544 - 64556]
  • 5
  • [ 6674-40-4 ]
  • [ 74-88-4 ]
  • [ 1265223-26-4 ]
  • [ 520-28-5 ]
  • [ 21392-57-4 ]
  • [ 23296-91-5 ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 16% 3: 7% 4: 10% With potassium carbonate In acetonitrile
Reference： [1]Location in patent: scheme or table Compton, Benjamin J.; Larsen, Lesley; Weavers, Rex T. [Tetrahedron, 2011, vol. 67, # 4, p. 718 - 726]
  • 6
  • [ 480-40-0 ]
  • [ 616-38-6 ]
  • [ 520-28-5 ]
  • [ 21392-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 30% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 48h;
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 100℃; 4.5.2. 7-O-methoxy and 5,7-di-O-methoxychrysin Synthesis 1,8-Diazabicyclo(5.4.0)undec-7-ene (10 mM) and CS (10 mM) were added in dimethyl carbonate(80 mL). The mixture solvent was synthesized at 100 °C for 12 h and then cooled in ice-cold water.The precipitate was separated by filtration and the solvent was removed with a rotary evaporator at40 °C. The residue was dissolved in DCM, washed in 1 M HCl 3 times, then washed with saturatedsodium bicarbonate solution and water to neutralize. The organic phase was separated, driedover MgSO4, and concentrated in vacuo. The resulting solid residue was purified using silica gelchromatography with DCM/MeOH (10:0 to 9.5:0.5, v/v) as the eluent, to yield 7-O-methoxychrysin(7-O-M) and 5,7-di-O-methoxychrysin (5,7-O-DM) [36].
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 19h; 1 [Synthesis Examples 4 and 5] Synthesis of 7-O-methoxy chrysin and 5,7-di-O-methoxy chrysin 2.54 g of chrysin (0.5 mmol) and 1.84 g of 1,8-diazabicyclo(5.4.0)undec-7-ene were mixed with 80 mL of DMC(dimethyl carbonate) and reacted at 90°C for 19 hours. The reaction product was concentrated with methanol (240 ml), and the resulting concentrate was fractionedwith ethyl acetate (200 ml) and 1N HCl (100 ml). The organic fraction layer (ethyl acetate) was concentrated, neutralized with NaCl, dehydrated with Na2SO4,and then subjected to silica gel column chromatography to separate 7-O-methoxy chrysin and 5,7-di-O-methoxy chrysin.
Reference： [1]Location in patent: experimental part Bernini, Roberta; Crisante, Fernanda; Ginnasi, Maria Cristina [Molecules, 2011, vol. 16, # 2, p. 1418 - 1425]
[2]Hwang, Seung Hwan; Kim, Hyun Yong; Zuo, Guanglei; Wang, Zhiqiang; Lee, Jae-Yong; Lim, Soon Sung [Molecules, 2018, vol. 23, # 7]
[3]Current Patent Assignee: FRONTBIO CO LTD - EP3747435, 2020, A1 Location in patent: Paragraph 0042; 0047-0049
  • 7
  • [ 21392-57-4 ]
  • [ 520-28-5 ]
YieldReaction ConditionsOperation in experiment
90% With boron tribromide In dichloromethane at 0℃; for 2h; Inert atmosphere;
84% With aluminum (III) chloride In acetonitrile at 0℃; Inert atmosphere; Reflux; Synthesis of 5-Hydroxyflavones (8); General Procedure General procedure: To a solution of the corresponding flavone (7) in dry acetonitrile (approx. 10mL per 1.0 mmol of flavone) at 0 °C in an ice-bath under N2 atmosphere was added a portion of AlCl3 (2.5 equiv). The mixture was stirred at this temperature and then was allowed to warm up to room temperature and was refluxed for 1.5-2 h. At this point the conversion was checked by TLC, the reaction was allowed to cool and an additional portion of AlCl3 (2.5 equiv) was added slowly to the reaction mixture and was refluxed for an additional 1.5-2 h. After completion, after cooling the reaction mixture was poured into crushed ice and 6N HCl (30 mL per mmol flavone) was added and the suspension was extracted with CH2Cl2 (3 x 60 mL per mmol flavone), the combined organic phases were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated under vacuum; the residue was treated with hexane and filtered to yield the pure compounds.
With boron tribromide In dichloromethane at -40 - 20℃; for 2h;
Reference： [1]Mokar, Bhanudas Dattatray; Yi, Chae S. [Organometallics, 2019, vol. 38, # 24, p. 4625 - 4632]
[2]Sipos, Zoltán; Kónya, Krisztina [Synthesis, 2018, vol. 50, # 8, p. 1610 - 1620]
[3]Choi, Yong-Sung; Kim, Yoon-Jung; Lee, Ju Yeun; Lee, Jinu; Jeong, Jin-Hyun [Heterocycles, 2014, vol. 89, # 12, p. 2794 - 2805]
  • 8
  • [ 570-02-5 ]
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Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4392 - 4396
  • 9
  • [ 54107-66-3 ]
  • [ 24388-23-6 ]
  • [ 21392-57-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 777 - 784
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

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