Home Cart 0 Sign in  

[ CAS No. 115841-09-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 115841-09-3
Chemical Structure| 115841-09-3
Structure of 115841-09-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 115841-09-3 ]

Related Doc. of [ 115841-09-3 ]

Alternatived Products of [ 115841-09-3 ]

Product Details of [ 115841-09-3 ]

CAS No. :115841-09-3 MDL No. :MFCD16660675
Formula : C26H20O10 Boiling Point : -
Linear Structure Formula :- InChI Key :GCJWPRRNLSHTRY-VURDRKPISA-N
M.W : 492.43 Pubchem ID :13991590
Synonyms :

Calculated chemistry of [ 115841-09-3 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 21
Fraction Csp3 : 0.08
Num. rotatable bonds : 8
Num. H-bond acceptors : 10.0
Num. H-bond donors : 6.0
Molar Refractivity : 128.63
TPSA : 177.89 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 4.07
Log Po/w (WLOGP) : 3.77
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : -5.36
Solubility : 0.00215 mg/ml ; 0.00000436 mol/l
Class : Moderately soluble
Log S (Ali) : -7.51
Solubility : 0.0000152 mg/ml ; 0.0000000309 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.88
Solubility : 0.00645 mg/ml ; 0.0000131 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.38

Safety of [ 115841-09-3 ]

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

Application In Synthesis of [ 115841-09-3 ]

* 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 [ 115841-09-3 ]

[ 115841-09-3 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 1141892-87-6 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: methanol; potassium carbonate / 24 h / 20 °C 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 2.2: 12 h / 65 °C / Inert atmosphere 3.1: piperidine; pyridine / 5 h / 100 °C 4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 6.1: boron tribromide / dichloromethane / -78 °C
  • 2
  • [ 1141892-88-7 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 1.2: 12 h / 65 °C / Inert atmosphere 2.1: piperidine; pyridine / 5 h / 100 °C 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 5.1: boron tribromide / dichloromethane / -78 °C
  • 3
  • [ 1388829-28-4 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: piperidine; pyridine / 5 h / 100 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 3: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 4: boron tribromide / dichloromethane / -78 °C
  • 4
  • [ 1388829-29-5 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 2: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 3: boron tribromide / dichloromethane / -78 °C
  • 5
  • [ 1388829-33-1 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 2: boron tribromide / dichloromethane / -78 °C
  • 6
  • [ 1388829-35-3 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
40% With boron tribromide In dichloromethane at -78℃;
  • 7
  • [ 1388829-24-0 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 1.2: 12 h / 65 °C / Inert atmosphere 2.1: piperidine; pyridine / 5 h / 100 °C 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 5.1: boron tribromide / dichloromethane / -78 °C
  • 8
  • [ 4049-39-2 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine; Iodine monochloride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 2.2: 12 h / 65 °C / Inert atmosphere 3.1: piperidine; pyridine / 5 h / 100 °C 4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 6.1: boron tribromide / dichloromethane / -78 °C
  • 9
  • [ 10403-73-3 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: iodine; silver sulfate / ethanol; dichloromethane / 1 h / 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 20 °C / Inert atmosphere 3.1: methanol; potassium carbonate / 24 h / 20 °C 4.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 4.2: 12 h / 65 °C / Inert atmosphere 5.1: piperidine; pyridine / 5 h / 100 °C 6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 8.1: boron tribromide / dichloromethane / -78 °C
  • 10
  • [ 5736-55-0 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 20 °C / Inert atmosphere 2.1: methanol; potassium carbonate / 24 h / 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 65 °C / Inert atmosphere 4.1: piperidine; pyridine / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 7.1: boron tribromide / dichloromethane / -78 °C
  • 11
  • [ CAS Unavailable ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 2.1: iodine; silver sulfate / ethanol; dichloromethane / 1 h / 20 °C 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 20 °C / Inert atmosphere 4.1: methanol; potassium carbonate / 24 h / 20 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 5.2: 12 h / 65 °C / Inert atmosphere 6.1: piperidine; pyridine / 5 h / 100 °C 7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 8.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 9.1: boron tribromide / dichloromethane / -78 °C
  • 12
  • [ CAS Unavailable ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / methanol / 5 h / Inert atmosphere; Reflux 1.2: 4 h / Reflux; Inert atmosphere 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 4.1: boron tribromide / dichloromethane / -78 °C
  • 13
  • [ 139-85-5 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate; sodium iodide / N,N-dimethyl-formamide / 48 h / 40 °C 2.1: pyridine; Iodine monochloride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 65 °C / Inert atmosphere 4.1: piperidine; pyridine / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 7.1: boron tribromide / dichloromethane / -78 °C
  • 14
  • [ 203798-74-7 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 2: hydrogenchloride; trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 24 h / Reflux 3: boron tribromide / dichloromethane / -78 °C
  • 15
  • salvianolic acid B [ No CAS ]
  • salvianolic acid D [ No CAS ]
  • lithospermic acid A [ No CAS ]
  • C26H22O10 [ No CAS ]
  • [ 1190422-00-4 ]
  • 4-(2-carboxyethenyl)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid 3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethyl] ester [ No CAS ]
  • C26H24O11 [ No CAS ]
  • 5,6-dihydroxy-3-(3,4-dihydroxyphenyl)-1-methyl-2-benzopyran-4-carboxylic acid 4-[1-carboxy-2-(3,4-dihydroxyphenyl)]ethyl ester [ No CAS ]
  • [ 23028-17-3 ]
  • [ 139-85-5 ]
  • (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoyl]oxypropanoic acid [ No CAS ]
  • salvianolic acid A [ No CAS ]
  • (E)-3-(2-((E)-3,4-dihydroxystyryl)-3,4-dihydroxyphenyl)acrylic acid [ No CAS ]
  • 7,8-dihydroxy-2-(3,4-dihydroxyphenyl)-1,2-dihydronaphthalene-1,3-dicarboxylic acid 3-(1-carboxy-2-(3,4-dihydroxyphenyl))ethyl ester [ No CAS ]
  • 16
  • [ 96574-01-5 ]
  • [ 1338058-98-2 ]
  • [ 1338058-99-3 ]
  • [ 1338059-01-0 ]
  • [ 1338059-00-9 ]
  • [ 142115-17-1 ]
  • [ 115841-09-3 ]
YieldReaction ConditionsOperation in experiment
In water at 90℃; Enrichment and isolation of degradation products Purified SalA (about 200 mg) was dissolved in distilled water (10 mL) and then heated at 90 °C in water bath. The post-react solvent was analyzed by the analytical HPLC to ensure that SalA was entirely transformed. At last four degradation products were isolated and purified from the post-react solvent by semi-preparative HPLC.
  • 17
  • [ 115841-09-3 ]
  • [ 1992772-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; potassium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 18
  • [ 115841-09-3 ]
  • [ 2016773-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; potassium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 19
  • [ 115841-09-3 ]
  • [ 2016773-24-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; sodium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 20
  • [ 115841-09-3 ]
  • [ 2016773-25-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; sodium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 21
  • [ 115841-09-3 ]
  • [ 2016773-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; sodium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 22
  • [ 115841-09-3 ]
  • [ 2016773-27-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere 4.1: water; sodium hydroxide / methanol; tetrahydrofuran / Reflux; Inert atmosphere
  • 23
  • [ 115841-09-3 ]
  • [ 434337-16-3 ]
YieldReaction ConditionsOperation in experiment
89% With lithium hydroxide monohydrate; potassium hydroxide In methanol Reflux; Inert atmosphere; 4.1.1 Tournefolic acid A (2) To a solution of salvianolic acid C (245mg, 0.498mmol) in MeOH/H2O (10mL, 4:1 v/v) was added potassium hydroxide (335mg, 5.576mmol). The mixture was stirred with reflux until the material spot disappeared by TLC under nitrogen atmosphere. After completing, the solution was concentrated to remove methanol. Then the residue was poured into 10% HCl solution (15mL) in an ice bath, and extracted with ethyl acetate (15mL×3). The organic layer was washed with brine, dried with anhydrous Na2SO4, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by column chromatography (chloroform/methanol/formic acid, 10/1/0.1 v/v/v) to afford tournefolic acid A (2) (138mg, yield 89%) as a yellow powder. 1H NMR (CD3OD, 300MHz) δ 7.92 (d, 1H, J=15.9Hz), 7.41-7.29 (m, 3H), 7.18 (s, 1H), 6.88 (d, 1H, J=8.1Hz), 6.73 (d, 1H, J=8.1Hz), 6.43 (d, 1H, J=15.9Hz); 13C NMR (CD3OD, 75MHz) δ 171.3, 159.3, 148.0, 146.7, 145.7, 144.6, 144.3, 132.5, 126.1, 123.4, 119.7, 118.7, 116.7, 116.0, 113.3, 111.7, 99.2. HR-MS (ESI) m/z: calcd. for C17H11O6 [M-H]-: 311.0561; found: 311.0563.
89% With lithium hydroxide monohydrate In methanol Sonication; Heating; 1.1 (1) Tournefolic acid A Accurate weighing Salvianolic acid C (1) (245 mg, 0 . 498mmol) in bottom bottle in two neck circles, adding MeOH/H2O 20 ml (5 1v/v), ultrasonic to a sample is completely dissolved, to accurately measure an amount of the inorganic alkali (NaOH or KOH), constantly under the heating condition the TLC (chloroform/methanol/formic acid 8 the [...] the 1 [...] 1v/v/v) monitoring the reaction, until the material completely disappeared. To be after the reaction is complete, is placed to room temperature, solvent evaporation to dryness MeOH, adding 15 ml distilled water, under ice bath to cool down, drop by adding 10% HCl aqueous solution and constantly stirring, to pH 3-4, stop dripping. Adding ethyl acetate (20 ml × 3) extraction, combined with the organic layer, saturated NaCl solution to wash, MgSO4drying, concentrating under reduced pressure, the crude reaction product obtained. Eluted by silica gel column chromatography or other degrees (chloroform/methanol/formic acid 10 the [...] the 1 [...] 0.1v/v/v), Tournefolic acid A product (138 mg, yield 89%).
89% In methanol; lithium hydroxide monohydrate Sonication; 1.1 1. Synthesis of 2-arylbenzofuran derivatives 2 Accurately weigh Salvianolic acid C(1) (1 equiv) in a 50 mL two-neck round bottom flask.Add MeOH/H2O 4 mL (5:1 v/v) and sonicate until the sample is completely dissolved.Add exactly the right amount of inorganic base (NaOH or KOH)Continuous TLC (chloroform/methanol/formic acid 8:1:1 v/v/v) detection reaction under heating conditionsUntil the raw material completely disappears. After the reaction is complete,Allow to warm to room temperature, evaporate the solvent MeOH, and dilute with 15 mL of distilled water.Ice water bath cooling,A 10% HCl aqueous solution was added dropwise with constant stirring until pH 3 to 4 and the dropwise addition was stopped.Ethyl acetate (20 mL x 4) was added for extraction and the organic layers were combined.The solution was washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure to give a crude reaction product.Elution was carried out on silica gel column chromatography (chloroform/methanol/formic acid 10:1:0.1 v/v/v).The target product Tournefolic acid A(2) (yield 89%) was obtained.
89% With lithium hydroxide monohydrate; potassium hydroxide In methanol Inert atmosphere; Reflux; 4.1.1 Tournefolic acid A (2) To a solution of salvianolic acid C (SAC, 1, 245mg, 0.498mmol) in MeOH/H2O (10mL, 4:1 v/v) was added potassium hydroxide (335mg, 5.576mmol). The mixture was stirred with reflux under nitrogen atmosphere until the material spot disappeared by TLC. After the reaction completed, the solution was concentrated to remove MeOH. Then the residue was poured into 10% HCl solution (15mL) in an ice bath, and then extracted with ethyl acetate (15mL×3). The organic layer was washed with brine, dried with anhydrous Na2SO4, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by column chromatography (the elute as chloroform/methanol/formic acid, 10/1/0.1 v/v/v) to afford tournefolic acid A (TAA, 2) (138mg, yield 89%) as a yellow powder. 1H NMR (CD3OD, 300MHz) δ 7.92 (d, 1H, J=15.9Hz), 7.41-7.29 (m, 3H), 7.18 (s, 1H), 6.88 (d, 1H, J=8.1Hz), 6.73 (d, 1H, J=8.1Hz), 6.43 (d, 1H, J=15.9Hz); 13C NMR (CD3OD, 75MHz) δ 171.3, 159.3, 148.0, 146.7, 145.7, 144.6, 144.3, 132.5, 126.1, 123.4, 119.7, 118.7, 116.7, 116.0, 113.3, 111.7, 99.2. HR-MS (ESI) m/z: calcd. for C17H11O6 [M-H]-: 311.0561; found: 311.0563.
89% With lithium hydroxide monohydrate In methanol Sonication; Heating; 1.1 (1) Tournefolic acid A Accurate weighing Salvianolic acid C (1) (245 mg, 0 . 498mmol) in bottom bottle in two neck circles, adding MeOH/H2O 20 ml (5 1v/v), ultrasonic to a sample is completely dissolved, to accurately measure an amount of the inorganic alkali (NaOH or KOH), constantly under the heating condition the TLC (chloroform/methanol/formic acid 8 the [...] the 1 [...] 1v/v/v) monitoring the reaction, until the material completely disappeared. To be after the reaction is complete, is placed to room temperature, solvent evaporation to dryness MeOH, adding 15 ml distilled water, under ice bath to cool down, drop by adding 10% HCl aqueous solution and constantly stirring, to pH 3-4, stop dripping. Adding ethyl acetate (20 ml × 3) extraction, combined with the organic layer, saturated NaCl solution to wash, MgSO4drying, concentrating under reduced pressure, the crude reaction product obtained. Eluted by silica gel column chromatography or other degrees (chloroform/methanol/formic acid 10 the [...] the 1 [...] 0.1v/v/v), Tournefolic acid A product (138 mg, yield 89%).

  • 24
  • [ 115841-09-3 ]
  • [ 115841-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 18 h / Reflux 2: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere
  • 25
  • [ 115841-09-3 ]
  • [ 1992772-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice
  • 26
  • [ 115841-09-3 ]
  • [ 1992772-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication; Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
  • 27
  • [ 115841-09-3 ]
  • [ 1992772-17-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication; Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
  • 28
  • [ 115841-09-3 ]
  • [ 1992772-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice
  • 29
  • [ 115841-09-3 ]
  • [ 1992772-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice
  • 30
  • [ 115841-09-3 ]
  • [ 2016773-17-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: water; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere
  • 31
  • [ 115841-09-3 ]
  • [ 1992772-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate; sodium hydroxide / methanol / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication; Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 32
  • [ 115841-09-3 ]
  • [ 1992772-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate; sodium hydroxide / methanol / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication; Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 33
  • [ 115841-09-3 ]
  • [ 1992772-20-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate; sodium hydroxide / methanol / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 34
  • [ 115841-09-3 ]
  • [ 1992772-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate; sodium hydroxide / methanol / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 35
  • [ 115841-09-3 ]
  • [ 1992772-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate; sodium hydroxide / methanol / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 36
  • [ 115841-09-3 ]
  • [ 2016773-18-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: water; potassium hydroxide / methanol / Reflux; Inert atmosphere 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 2.2: 20 °C / Inert atmosphere 3.1: water; sodium hydroxide / methanol / Reflux; Inert atmosphere
  • 37
  • [ 115841-09-3 ]
  • [ 1992772-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 38
  • [ 115841-09-3 ]
  • [ 1992772-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 39
  • [ 115841-09-3 ]
  • [ 2016773-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 40
  • [ 115841-09-3 ]
  • [ 2016773-20-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 41
  • [ 115841-09-3 ]
  • [ 2016773-21-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 42
  • [ 115841-09-3 ]
  • [ 2016773-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: water; potassium hydroxide / methanol; tetrahydrofuran / 12 h / Reflux; Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; dichloromethane / 0.25 h / 0 °C 3.2: 20 °C / Inert atmosphere
  • 43
  • [ 77-78-1 ]
  • [ 115841-09-3 ]
  • [ 115841-16-2 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In propan-2-one for 18h; Reflux; 4.1.5 (2R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yl (2E)-3-[2-(3,4-dimethoxyphenyl)-7-methoxy-1-benzofuran-4-yl]prop-2-enoate (7) Salvianolic acid C (206mg, 0.419mmol) was placed into a boiling flask and dispersed in 15mL of acetone containing anhydrous potassium carbonate (1.16g, 8.374mmol). To the suspension 714.5μL (7.542mmol) of dimethyl sulfate was added, and the reaction mixture was stirred for 18h under reflux. After completing, acetone was removed by a rotary evaporator. The residue was suspended in saturated NH4Cl resolution (15mL) and then extracted with ethyl acetate (20mL×4). The organic layer was washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuum. The obtained residue was further separated by silica gel chromatography using chroloform/methanol as the eluent to give pure compound 7 as a yellow foam (230mg, yield 95%). 1H NMR (CDCl3, 300MHz) δ 7.96 (d, 1H, J=15.9Hz), 7.53 (dd, 1H, J=8.4, 2.1Hz), 7.39 (m, 2H), 7.17 (s, 1H), 6.97 (d, 1H, J=8.4Hz), 6.82 (m, 4H), 6.50 (d, 1H, J=15.9Hz), 5.41 (m, 1H), 4.09 (s, 3H), 4.03 (s, 3H), 3.96 (s, 3H), 3.88 (s, 3H), 3.86 (s, 3H), 3.78 (s, 3H), 3.21-2.80 (m, 2H); 13C NMR (CDCl3, 75MHz) δ 170.5, 166.7, 157.6, 150.1, 149.2, 148.8, 148.8, 146.9, 144.1, 143.7, 130.7, 128.4, 125.8, 122.7, 121.4, 121.4, 118.5, 114.9, 112.5, 111.3, 111.2, 108.2, 106.6, 99.2, 73.1, 56.2, 56.2, 56.0, 55.8, 55.8, 52.4, 37.2. HR-MS (ESI) m/z: calcd. for C32H33O10 [M+H]+: 577.2079; found: 577.2068.
92% With potassium carbonate Sonication; Reflux; 7 (2R) - 3 - (3,4-dimethoxyphenyl) - 1-methoxy-1-oxopropan-2-yl (2E) - 3 - [2 - (3,4-dimethoxyphenyl) - 7-methoxy-1-benzofuran-4-yl] prop-2-enoate (7) Accurate weighing Salvianolic acid C (206 mg, 0 . 419mmol) in the round bottom b neck flask, plus 15mLMe2CO ultrasonic dissolved, (quantity) that the accurate K2CO3(1.16g, 8 . 374mmol), Me2SO4(714.5 ml, 7 . 542mmol) salvianolic acid C in the sample solution is added, reflux reaction, and TLC (cyclohexane/ethyl acetate the 1 [...] 1) monitoring, basically disappear until the reaction raw materials. After the reaction terminates, the solvent evaporation to dryness, saturated NH4Cl aqueous solution (20 ml) dilution, using ethyl acetate (20 ml × 4) extraction, combined with the organic layer, the saturated salt water washing, MgSO4drying, concentrating under reduced pressure, the mixture, which is obtained by the sample. For gradient elution of the silica gel column (cyclohexane/ethyl acetate 10 the [...] 1, the 5 [...] 1v/v), to obtain a reaction product 7 (431 mg, yield 92%).
92% With potassium carbonate Sonication; Reflux; 7 (2R) - 3 - (3,4-dimethoxyphenyl) - 1-methoxy-1-oxopropan-2-yl (2E) - 3 - [2 - (3,4-dimethoxyphenyl) - 7-methoxy-1-benzofuran-4-yl] prop-2-enoate (7) Accurate weighing Salvianolic acid C (206 mg, 0 . 419mmol) in the round bottom b neck flask, plus 15mLMe2CO ultrasonic dissolved, (quantity) that the accurate K2CO3(1.16g, 8 . 374mmol), Me2SO4(714.5 ml, 7 . 542mmol) salvianolic acid C in the sample solution is added, reflux reaction, and TLC (cyclohexane/ethyl acetate the 1 [...] 1) monitoring, basically disappear until the reaction raw materials. After the reaction terminates, the solvent evaporation to dryness, saturated NH4Cl aqueous solution (20 ml) dilution, using ethyl acetate (20 ml × 4) extraction, combined with the organic layer, the saturated salt water washing, MgSO4drying, concentrating under reduced pressure, the mixture, which is obtained by the sample. For gradient elution of the silica gel column (cyclohexane/ethyl acetate 10 the [...] 1, the 5 [...] 1v/v), to obtain a reaction product 7 (431 mg, yield 92%).
  • 44
  • [ 115841-09-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice
  • 45
  • [ 115841-09-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol / Sonication; Heating 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C / Sonication 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / Reflux
  • 46
  • lithospermic acid [ No CAS ]
  • [ 23028-17-3 ]
  • [ 142115-17-1 ]
  • (2S,3S)-4-[(E)-2-carboxyethenyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid [ No CAS ]
  • (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoyl]oxypropanoic acid [ No CAS ]
  • salvianolic acid A [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer; water-d2; at 100℃;pH 4.75;Sealed tube; Inert atmosphere;Kinetics; Twelve or more test tubes were laid in a thermostat bath at predefined temperature and were periodically withdrawn during a kinetic run.Withdrawn samples were rapidly cooled in ice to quench the reaction and were stored in an ice bath until analysis within 2 h. Each study was comprised of twelve or more assays spaced to provide change of ~ 0.1 C01 per samples. After NMR analysis, degradation samples were diluted with an equal volume of 0.3M phosphoric acid. 2 muL diluted samples were injected into LC-MSn system for tentative structure elucidation of the degradation products. The influences of temperature and pH values on degradation of LA were investigated. The influence of temperature on degradation was investigated in phosphate buffer solutions at a pH value of 4.75. The reaction rate constants were calculated at 80, 91 and 100C, respectively. The effect of pH values on degradation was determined at 91C in phosphate buffer solutions. Specific experimental conditions were listed in Table 2. All the pH measurements were performed on a pH meter (S40 SevenMulti,Mettler-Toledo GmbH, Greifensee, Switzerland) equipped with combination pH electrode (InLab Expert Pro).
  • 47
  • [ 115841-09-3 ]
  • [ 2172933-97-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol; water / Sonication 2.1: thionyl chloride / 0.5 h / Cooling with ice 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / methanol / Inert atmosphere; Reflux 2.1: 0.5 h / 0 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere
  • 48
  • [ 115841-09-3 ]
  • [ 2172933-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol; water / Sonication 2.1: thionyl chloride / 0.5 h / Cooling with ice 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / methanol / Inert atmosphere; Reflux 2.1: 0.5 h / 0 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere
  • 49
  • [ 115841-09-3 ]
  • [ 2172933-99-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol; water / Sonication 2.1: thionyl chloride / 0.5 h / Cooling with ice 2.2: 20 °C
  • 50
  • [ 115841-09-3 ]
  • [ 2172933-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol; water / Sonication 2.1: thionyl chloride / 0.5 h / Cooling with ice 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / methanol / Inert atmosphere; Reflux 2.1: thionyl chloride / 0.5 h / 0 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere
  • 51
  • [ 115841-09-3 ]
  • [ 1675220-28-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol; water / Sonication 2.1: thionyl chloride / 0.5 h / Cooling with ice 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / methanol / Inert atmosphere; Reflux 2.1: 0.5 h / 0 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere
Same Skeleton Products
Historical Records