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[ CAS No. 53188-07-1 ]

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Chemical Structure| 53188-07-1
Chemical Structure| 53188-07-1
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CAS No. :53188-07-1 MDL No. :MFCD00006846
Formula : C14H18O4 Boiling Point : 450.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :250.29 g/mol Pubchem ID :-
Synonyms :

Safety of [ 53188-07-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53188-07-1 ]

  • Downstream synthetic route of [ 53188-07-1 ]

[ 53188-07-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 15837-47-5 ]
  • [ 53188-07-1 ]
  • 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (6-amino-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: trolox With triethylamine; Diphenylphosphinic chloride In ethyl acetate for 1h; cooling; Stage #2: 1-phenyl-2,4-dioxo-5,6-diaminopyrimidine With triethylamine In ethyl acetate at 20℃; for 3h;
  • 2
  • [ 36653-82-4 ]
  • [ 53188-07-1 ]
  • (±)-6-hydroxy-2,5,7,8-tetramethyl chroman-2-carboxylic acid hexadecyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With dmap; 2-chloro-1-methyl-pyridinium iodide In 1,4-dioxane Large scale; 4.1 1) Synthesis of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester 1) Synthesis of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester Procedure: Under electromagnetic stirring, to a 100 mL reaction flask hexadecanol (970 mg, 4 mmol), 4-dimethylaminopyridine (1466 mg, 12 mmo), 2-chloro-1-methylpyridinium iodide (1533 mg, 6 mmol) and dioxane (20 mL) were added, and then to the reaction solution a solution of (+-)-6-hydroxy- 2,5,7,8-tetramethylchroman-2-carboxylic acid (1001 mg, 4 mmol) in dioxane (20 mL) was slowly dropwise added. The reaction mixture was reacted for 12 h at room temperature under the protection of nitrogen gas and electromagnetic stirring. The solvent (dioxane) was removed by a rotary evaporator, and thereto diethyl ether (50 mL) was added. The resulting mixture was stirred for 2 h, and the precipitate was removed by filtration. The filtrate was concentrated to 10 mL, and isolated by column chromatography (the stationary phase was 230-400 mesh silica gel, the eluent was hexane : ethyl acetate = 10:1), to obtain (+-)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester (1242 mg, yield 65.4%). MS(Positive ESI): m/z = 475.3(M+H)+, 497.3(M+Na)+,971.5(2M+Na)+. 1H NMR (400 MHz, CDCl3) δ ppm: 4.167 (s, 1H), 4.077-3.974 (m, 2H), 2.647-2.383 (m, 3H), 2.160 (s, 3H), 2.135 (s, 3H), 2.037 (s, 3H), 1.878-1.801 (m, 1H), 1.577 (s, 3H), 1.535-1.471 (m, 2H), 1.282-1.174 (m, 26H), 0.879-0.844 (t, J = 7.0 Hz, 3H).
65.4% With dmap; 2-chloro-1-methyl-pyridinium iodide In 1,4-dioxane at 20℃; for 12h; Inert atmosphere; 4.1 1) Synthesis of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester Under electromagnetic stirring, to a 100 mL reaction flask hexadecanol (970 mg, 4 mmol), 4-dimethylaminopyridine (1466 mg, 12 mmo), 2-chloro-1-methylpyridinium iodide (1533 mg, 6 mmol) and dioxane (20 mL) were added, and then to the reaction solution a solution of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1001 mg, 4 mmol) in dioxane (20 mL) was slowly dropwise added. The reaction mixture was reacted for 12 h at room temperature under the protection of nitrogen gas and electromagnetic stirring. The solvent (dioxane) was removed by a rotary evaporator, and thereto diethyl ether (50 mL) was added. The resulting mixture was stirred for 2 h, and the precipitate was removed by filtration. The filtrate was concentrated to 10 mL, and isolated by column chromatography (the stationary phase was 230-400 mesh silica gel, the eluent was hexane:ethyl acetate=10:1), to obtain (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester (1242 mg, yield 65.4%). MS (Positive ESI): m/z=475.3 (M+H)+, 497.3 (M+Na)+, 971.5 (2M+Na)+. 1H NMR (400 MHz, CDCl3) δ ppm: 4.167 (s, 1H), 4.077-3.974 (m, 2H), 2.647-2.383 (m, 3H), 2.160 (s, 3H), 2.135 (s, 3H), 2.037 (s, 3H), 1.878-1.801 (m, 1H), 1.577 (s, 3H), 1.535-1.471 (m, 2H), 1.282-1.174 (m, 26H), 0.879-0.844 (t, J=7.0 Hz, 3H).
65.4% With dmap; 2-chloro-1-methyl-pyridinium iodide In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; The synthesis of alkyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate/carboxamide (2) General procedure: A solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1, 3 mmol) in 10 mL N,N’-dimethylformamide(DMF) was added slowly to the stirring solution of appropriate aliphatic alcohol/ammine (3 mmol), dimethylaminopyridine(DMAP, 6 mmol) and 2-Chloro-1-methylpyridinium iodide (CMPI, 3 mmol) in DMF (20mL) in a 50 ml flask. The stirring was continued at roomtemperature under the atmosphere of nitrogen for 12 h andthe completion of reaction was monitored by thin layerchromatography (TLC). The reaction on completion wasevaporated under reduced pressure, and mixed with diethylether (50 mL). After 2 h of stirring, the mixture was filtered,and the filtrate was separated by chromatography (silica gel,230-400 mesh) eluted by hexane/ethyl acetate.
  • 3
  • [ 343778-59-6 ]
  • [ 53188-07-1 ]
  • N-(1-(3-chlorobenzyl)piperidin-4-yl)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;
  • 4
  • [ 138-14-7 ]
  • [ 53188-07-1 ]
  • N1-hydroxy-N-(5-(4-(hydroxy(1-(6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxamido)-1λ5,5λ3-pentyl)amino)-4-oxobutanamido)pentyl)-N4-(5-(N-hydroxyacetamido)pentyl)succinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.8% Stage #1: trolox With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: deferoxamine mesylate In N,N-dimethyl-formamide for 16h; Inert atmosphere; N1 -hydroxy-N1 -(5-(4-(hydroxy( 1 -(6-hydroxy-2, 5,7 8-tetram ethylchrom ane-2- carboxam ido)-1 X5,5X3-pentyl)amino)-4-oxobutanamido)pentyl)-N4-(5-(N-hydroxyacetamido)pentyl)succinamide (DFOB-(rac)-TLX) (±)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (rac-TLX; 50.0 mg,0.20 mmol), EDC (57.4 mg, 0.30 mmol) and HOBt (40.5 mg, 0.30 mmol) were dissolved in anhydrous dimethylformamide (2.2 mL), DIPEA (52.2 pL, 0.30 mmol) was added and the reaction mixture was stirred under nitrogen for 1 h. Desferrioxaminemesylate (157.5 mg, 0.24 mmol) was added and the solution was kept stirring under nitrogen for16 h. The reaction was stopped by adding ice cold water (0.5 mL) and the solvents were removed under reduced pressure. The residue was suspended in water and the suspension loaded onto a RP-C18 cartridge (2g bed weight). After washing the cartridge and residue with water (10 mL) and water:acetonitrile (9:1; 10 mL), the product was eluted with acetonitrile (10 mL) and methanol (10 mL). The organic eluates werecombined and the solvents removed under reduced pressure. The residue was redissolved in warm methanol, filtered (0.22 pm) and separated by RP-HPLC (Shimadzu system, semipreparative C18 ShimPack GIS column (10 x 150 mm, 5 p)7 5 mL/min, isocratic mode at 29% acetonitrile:aqueous TFA (0.05%)). The peak eluting at 21.1 mm was collected. The combined fractions were reduced under pressure and the aqueous solution frozen and freeze-dried to yield DFOB-(rac)-TLX as an off-white powder (109.0 mg, 68.8%).1H NMR (400 MHz, DMSO-d6) O 9.66, 7.78, 7.49, 7.22, 3.45, 3.37, 3.00, 2.57,2.45-2.37, 2.26, 2.19-2.13, 2.09, 2.07, 1.99, 1.96, 1.74-1.67, 1.51-1.47, 1.41-1.30, 1.36,1.25-1.19, 1.05-1.01 (Figure 3).l3 NMR (100 MHz, DMSO-d6) O 173.12, 171.94, 171.32, 171.29, 170.13,145.82, 143.91, 122.70, 121.17, 120.29, 117.12, 77.24, 47.08, 46.79, 39.52, 38.44,38.27, 29.92, 29.51, 28.85, 28.76, 27.60, 26.06, 26.01, 24.18, 23.52, 23.14, 20.39,20.16,12.81,12.10,11.83 (Figure 4).
  • 5
  • [ 53188-07-1 ]
  • [ 947-84-2 ]
  • (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methyl [1,1′-biphenyl]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Synthesis of Target Compounds 3-18 General procedure: The synthetic method to prepare compounds 3-18 was reported in ourprevious work [20]. Substituted benzoic acid (0.4 mmol) and anhydrous THF (1 mL) were added to a dry standard Schlenk tube. DMAP (4.9 mg, 0.04 mmol), compound 2 (99.4 mg, 0.4 mmol), and DCC (90.7 mg, 0.44 mmol) were then added, and the reaction was carried out at room temperature for 12 h. The solvent was evaporated under reduced pressure and the residue dissolved in EtOAc (15 mL). The sample was washed sequentially using saturated aqueous solutions of sodium bicarbonate and sodium chloride. The sample was then dried over anhydrous sodium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to give the desired compound.
  • 6
  • [ 3839-22-3 ]
  • [ 53188-07-1 ]
  • (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methyl 2-cyanobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Synthesis of Target Compounds 3-18 General procedure: The synthetic method to prepare compounds 3-18 was reported in ourprevious work [20]. Substituted benzoic acid (0.4 mmol) and anhydrous THF (1 mL) were added to a dry standard Schlenk tube. DMAP (4.9 mg, 0.04 mmol), compound 2 (99.4 mg, 0.4 mmol), and DCC (90.7 mg, 0.44 mmol) were then added, and the reaction was carried out at room temperature for 12 h. The solvent was evaporated under reduced pressure and the residue dissolved in EtOAc (15 mL). The sample was washed sequentially using saturated aqueous solutions of sodium bicarbonate and sodium chloride. The sample was then dried over anhydrous sodium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to give the desired compound.
  • 7
  • [ 36039-36-8 ]
  • [ 53188-07-1 ]
  • 2-(4-isobutylphenyl)propyl6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h; 3.1.4. General Synthesis of Compounds 14-17 General procedure: To a cooled (0 C) solution of 1 mmol of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid in dry dichloromethane, 3 mmol of the corresponding alcohol b, d, f or n,1.1 mmol N,N-dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridinewere added. The reaction mixture was stirred at 0 C for 5 min and at room temperaturefor 5 h (or 3 days for compound 17) and then filtered. The filtrate was diluted withdichloromethane, washed with 0.5N HCl solution and NaHCO3 5% solution, dried overanhydrous sodium sulfate and evaporated to dryness. The crude product was purified byflash chromatography to yield the final compounds 14-17.2-(4-isobutylphenyl)propyl6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylate (14) Yield:94%, white solid. m.p.: 69.2-70.0 C. 1H NMR (400 MHz, CDCl3), (ppm): 0.94 (d, 6H,-CH(CH3)2)), 1.21 (d, 3H, -CH(CH3)), 1.33 (dd, J = 9.0, 5.7 Hz, 1H, -CH(CH3)2), 1.56 (d,J = 3.8 Hz, 3H, 2-CH3), 1.78-1.93 (m, J = 19.3, 8.6, 4.5 Hz, 2H, 3-CH2), 2.06 (d, J = 5.4 Hz, 3H,8-CH3), 2.20 (d, J = 7.8 Hz, 6H, 5,7-CH3), 2.30-2.42 (m, 1H, 1/2x 4-CH2), 2.47 (d, J = 10.7 Hz,2H, -CH2CH(CH3)2), 2.52-2.64 (m, 1H, 1/2 4-CH2), 3.04 (sex, 1H, -CH(CH3)), 4.07-4.16(m, J = 8.8, 6.5, 2.5 Hz, 1H, 1/2 -OCH2-), 4.19-4.30 (m, 1H, 1/2 -OCH2-), 4.36 (brs, 1H,-OH), 7.09 (d, J = 2.4 Hz, 4H, aromatic). 13C NMR (101 MHz, CDCl3), (ppm): 11.22 (5-CH3),11.82 (7-CH3), 12.21 (8-CH3), 17.74 (-CH(CH3)), 20.84 (-C(CH3)), 22.38 (-CH(CH3)2), 25.50(3-CH2), 30.23 ((-CH(CH3)2), 30.60 (4-CH2), 38.55 (-CH(CH3)), 45.04 (-CH2CH(CH3)2), 70.04(-OCH2-), 77.00 (-C(CH3)), 116.89 (4a-chromane), 118.35 (5-chromane), 121.13 (7-chromane),122.49 (8-chromane), 126.96 (3,5-phenyl), 129.14 (2,6-phenyl), 139.99 (4-phenyl), 140.26(1-phenyl), 145.24 (6-chromane), 145.64 (8a-chromane), 173.83 (C=O).
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