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Chemical Structure| 499-05-8 Chemical Structure| 499-05-8

Structure of 499-05-8

Chemical Structure| 499-05-8

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Product Details of [ 499-05-8 ]

CAS No. :499-05-8
Formula : C6H4O4
M.W : 140.09
SMILES Code : O=C(C1=CC(C=CO1)=O)O
MDL No. :MFCD00059958
InChI Key :UFMDRPPBUAPWBK-UHFFFAOYSA-N
Pubchem ID :12305536

Safety of [ 499-05-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 499-05-8 ]

* 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 [ 499-05-8 ]

[ 499-05-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 499-05-8 ]
  • [ 108-97-4 ]
  • 2
  • [ 499-05-8 ]
  • 4-hydroxy-tetrahydro-pyran-2-carboxylic acid [ No CAS ]
  • 3
  • [ 499-05-8 ]
  • [ 4759-46-0 ]
  • 4
  • [ 1551-45-7 ]
  • [ 499-05-8 ]
  • 5
  • [ 99-32-1 ]
  • [ 499-05-8 ]
  • 6
  • [ 6556-12-3 ]
  • [ 108-24-7 ]
  • [ 499-05-8 ]
  • [ 95722-14-8 ]
  • 7
  • [ 95722-14-8 ]
  • [ 499-05-8 ]
  • [ 76539-65-6 ]
  • 8
  • [ 95722-13-7 ]
  • [ 499-05-8 ]
  • [ 95722-14-8 ]
  • [ 76539-65-6 ]
  • 9
  • [ 62133-77-1 ]
  • [ 499-05-8 ]
  • 12
  • chlorocomanic acid [ No CAS ]
  • [ 499-05-8 ]
  • 13
  • dichlorocomanic acid [ No CAS ]
  • [ 499-05-8 ]
  • 14
  • [ 499-05-8 ]
  • [ 7732-18-5 ]
  • alkaline earth hydroxide [ No CAS ]
  • [ 64-18-6 ]
  • [ 144-62-7 ]
  • [ 67-64-1 ]
  • 15
  • [ 499-05-8 ]
  • [ 100-46-9 ]
  • [ 276869-38-6 ]
  • 4-oxo-4<i>H</i>-pyran-2-carboxylic acid [1-benzylcarbamoyl-2-(3-hydroxycarbamoyl-propylsulfanyl)-ethyl]-amide [ No CAS ]
  • 16
  • [ 685-73-4 ]
  • [ 499-05-8 ]
  • 17
  • [ 95722-13-7 ]
  • [ 499-05-8 ]
  • 18
  • [ 499-05-8 ]
  • 4-hydroxy-tetrahydro-pyran-2-carboxylic acid-(4-phenyl-phenacyl ester) [ No CAS ]
  • 19
  • [ 499-05-8 ]
  • [ 320780-86-7 ]
  • [ 320781-48-4 ]
  • 20
  • [ 499-05-8 ]
  • [ 444912-95-2 ]
  • N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)-methyl)ethyl)-4-oxo-4H-pyran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); To a solution of 1-(4-fluorophenyl)-1-oxo-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (600 mg, 1.73 mmol) and <strong>[499-05-8]4-oxo-4H-pyran-2-carboxylic acid</strong> (266 mg, 1.90 mmol) in N,N-dimethylformamide (10 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (496 mg, 2.59 mmol), 1-hydroxy-1H-benzotriazole (396 mg, 2.59 mmol) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.28 ml, 1.90 mmol) and the mixture was stirred overnight. To the reaction solution were added 1N aqueous hydrochloric acid solution (10 ml) and water (100 ml) and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl) methyl)ethyl)-4! -oxo-4H-pyran-2-carboxamide (570 mg, 76%). mp 115-116C IR nu maxKBrcm-1: 1661, 1620, 1597, 1510, 1412. Anal. Calcd for C22H15F4NO4·0.1H2O: C, 60.72; H, 3.52; N, 3.22 Found: C, 60.60; H, 3.55; N, 3.24.1H-NMR (CDCl3) delta: 3.23 (1H, dd, J = 14.0, 5.2 Hz), 3.43 (1H, dd, J = 14.0, 5.2 Hz), 5.93 (1H, q, J = 6.4 Hz), 6.44 (1H, dd, J = 5.8, 2.6 Hz), 7.07 (2H, d, J = 8.0 Hz), 7.10-7.26 (2H, m), 7.48 (2H, d, J = 8.0 Hz), 7.59 (1H, d, J = 7.4 Hz), 7.77 (1H, d, J = 6.0 Hz), 7.92-8.06 (2H, m).
  • 21
  • [ 499-05-8 ]
  • [ 608-07-1 ]
  • N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-oxo-4H-pyran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 6.25h; Under an argon atmosphere, a 100 ml three-necked flask round-bottom flask was charged with <strong>[499-05-8]comanic acid</strong> (500 mg, 1 equiv.) and 5-methoxytryptamine (760 mg, 1.1 equiv.), dissolved in DMF (25 ml), and brought to O0C by means of an ice-bath. HOBt (1-hydroxybenxotriazole monohydrate, 530 mg, 1.1 equiv.), EDC ( 1 -(3 -dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 750 mg, 1.1 equiv,) and triethylamine (1.25 ml, 2.5 equiv.) were then added under magnetic stirring. The <n="34"/>mixture was stirred for an additional 15 minutes at O0C and subsequently allowed to react for 6 h at room temperature. The reaction course was followed by HPLC-MS. Water (50 ml) was then added and the mixture was extracted with dichloromethane (3 x 50 ml). The combined organic phases were dried over Na2SO4 and the solvent was removed by rotary evaporation. The crude was then chromatographed over a silica gel column by eluting with dichloromethane / methanol 95 / 5. The product was recovered as a bright yellow solid (235 mg, yield 21 %).Experimental data for N-[2-(5-methoxy-indol-3-yl)-ethyl]-comanilamide MS (ESI POS): 313 (M + H), 330 (M + H2O), 335 (M + Na), 376 (M + Na + CH3CN) HPLC assay: 98%1H NMR (DMSOd6, 400MHz) delta 2.88-2.92 (m, 2H, CH2CH2NH), 3.48-3.53 (m, 2H, CH2CH2NH), 3.75 (s, 3H, OCH3), 6.42 (dd, J1= 2.3 Hz, J2= 5.9 Hz, IH, CH=CH), 6.71 (dd, J1= 2.1 Hz, J2 = 8.8 Hz, IH, aromatic H), 6.78 (d, J = 2.3 Hz, IH, aromatic H), 7.04 (d, J = 2.3 Hz, IH, CH), 7.13 (d, J = 2.1 Hz, IH, aromatic H), 7.22 (d, J = 8.8 Hz, IH, aromatic H), 8.21 (d, J = 5.9 Hz, IH, CH=CH-CO), 9.04 (br t, J = 5.8 Hz, IH, CH2CH2NH), 10.65 (br s, IH5 NH).
21% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 6.25h;Inert atmosphere; Under an argon atmosphere, a 100 ml three-necked flask round-bottom flask was charged with <strong>[499-05-8]comanic acid</strong> (500 mg, 1 equiv.) and 5-methoxytryptamine (760 mg, 1.1 equiv.), dissolved in DMF (25 ml), and brought to 0 C by means of an ice-bath. HOBt (1-hydroxybenxotriazole monohydrate, 530 mg, 1.1 equiv.), EDC (1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 750 mg, 1.1 equiv.) and triethylamine (1.25 ml, 2.5 equiv.) were then added under magnetic stirring. The mixture was stirred for an additional 15 minutes at 0 C and subsequently allowed to react for 6 h at room temperature. The reaction course was followed by HPLC-MS. Water (50 ml) was then added and the mixture was extracted with dichloromethane (3×50 ml). The combined organic phases were dried over Na2SO4 and the solvent was removed by rotary evaporation. The crude was then chromatographed over a silica gel column by eluting with dichloromethane/methanol 95/5. The product was recovered as a bright yellow solid (235 mg, yield 21%).Experimental data for N-[2-(5-methoxy-indoi-3-yi)-ethyi]-comanilamide MS (ESI POS): 313 (M+H), 330 (M+H20), 335 (M+Na), 376 (M-*-Na+CH3CN)
  • 22
  • [ 499-05-8 ]
  • [ 59-88-1 ]
  • [ 1240489-64-8 ]
  • 23
  • [ 499-05-8 ]
  • [ 100-63-0 ]
  • [ 1240489-63-7 ]
YieldReaction ConditionsOperation in experiment
35% General procedure: A mixture of 4-pyrone (1.5 mmol) and PhNHNH2 (3.3 mmol) in aprotic solvent (dioxane, toluene) was heated for several hours
  • 24
  • [ 499-05-8 ]
  • [ 100-63-0 ]
  • [ 1240489-66-0 ]
  • 25
  • [ 499-05-8 ]
  • [ 22483-09-6 ]
  • [ 1357289-11-2 ]
YieldReaction ConditionsOperation in experiment
76% In water; at 65 - 100℃; for 5h; Water (2.5 mL) and aminoacetaldehyde dimethyl acetal (756 muL, 7.0 mmol) were added to compound 14A (1.0 g, 7.1 mmol) at room temperature. The mixture was stirred at 65C for 1.5 hours and then stirred at 100C for 3.5 hours. After concentration to dryness, crystals were deposited by the addition of water (5 mL). 2-propanol (10 mL) was added thereto, followed by filtration. The crystals were washed with 2-propanol (5 mL) and through-flow-dried to obtain 0.98 g (yield: 76%) of crystals of compound 14B. 1H-NMR (CDCl3) delta: 4.56 (2H, d, J = 4.9 Hz), 5.38 (1H, t, J = 4.9 Hz), 7.16 (1H, dd, J = 7.3 Hz, 2.9 Hz), 7.26 (1H, d, J = 2.9 Hz), 8.31 (1H, d, J = 7.3 Hz).
  • 26
  • [ 499-05-8 ]
  • [ 1357289-13-4 ]
  • 27
  • [ 499-05-8 ]
  • [ 1357289-15-6 ]
  • 28
  • [ 499-05-8 ]
  • [ 1357289-17-8 ]
  • 29
  • sodium (5E)-6-(dimethylamino)-1-ethoxy-5-(ethoxycarbonyl)-1,4-dioxohexa-2,5-dien-2-olate [ No CAS ]
  • [ 499-05-8 ]
  • 31
  • 4-oxo-4H-pyran-2,5-dicarboxylic acid [ No CAS ]
  • [ 499-05-8 ]
  • 32
  • diethyl 2-hydroxy-4-oxo-5-(piperidin-1-ylmethylidene)hex-2-enedioate [ No CAS ]
  • [ 499-05-8 ]
  • 33
  • [ 499-05-8 ]
  • [ 100-63-0 ]
  • (E)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-3-yl)propionic acid [ No CAS ]
  • (Z)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-3-yl)propionic acid [ No CAS ]
  • (E)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-5-yl)propionic acid [ No CAS ]
  • (Z)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-5-yl)propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; for 8h;Reflux; General procedure: A mixture of 4-pyrone (1.5 mmol) and PhNHNH2 (3.3 mmol) in aprotic solvent (dioxane, toluene) was heated for several hours
  • 34
  • [ 499-05-8 ]
  • [ 59-88-1 ]
  • (E)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-3-yl)propionic acid [ No CAS ]
  • (E)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-5-yl)propionic acid [ No CAS ]
  • (Z)-2-(phenylhydrazono)-3-(1-phenyl-1H-pyrazol-5-yl)propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With hydrogenchloride; acetic acid; In water; at 60℃; for 8h; General procedure: A mixture of 4-pyrone (1.5 mmol) and PhNHNH2·HCl (3.3 mmol) in protic solvent (H2O, EtOH, AcOH) was heated for several hours.
  • 35
  • [ 499-05-8 ]
  • [ 5270-59-7 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 16h;Inert atmosphere; To a degassed solution of <strong>[499-05-8]4-oxo-4H-pyran-2-carboxylic acid</strong> (7 g, 50.0 mmol, I eq) in EtOAc (130 mL) was added palladium/carbon (0.700 g,10% by weight) and the mixture was again degassed thoroughlywith Ar and stirred in a paar shaker for 16 h under H2. Reaction was monitored by TLC .The RM was filtered through celite bed and organic portion was concentrated under reduced pressure to crude 4- oxotetrahydro-2H-pyran-2-carboxylic acid (3.8 g, 53%) as white solid which was used for next step without further purification.
 

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