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[ CAS No. 10543-12-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 10543-12-1
Chemical Structure| 10543-12-1
Chemical Structure| 10543-12-1
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Product Details of [ 10543-12-1 ]

CAS No. :10543-12-1 MDL No. :MFCD00016515
Formula : C10H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :WTPDKEAYVAXNRO-UHFFFAOYSA-N
M.W : 210.18 Pubchem ID :66346
Synonyms :

Calculated chemistry of [ 10543-12-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.39
TPSA : 72.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 1.32
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.87 mg/ml ; 0.0089 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.63 mg/ml ; 0.003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.98
Solubility : 2.19 mg/ml ; 0.0104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 10543-12-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10543-12-1 ]

* 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 [ 10543-12-1 ]

[ 10543-12-1 ] Synthesis Path-Downstream   1~94

  • 5
  • [ 10543-12-1 ]
  • [ 99185-39-4 ]
  • 6
  • [ 10543-12-1 ]
  • 4-acetoxy-2-bromo-5-methoxy-benzoic acid [ No CAS ]
  • 7
  • [ 10543-12-1 ]
  • [ 90-05-1 ]
  • 8
  • [ 34749-55-8 ]
  • [ 10543-12-1 ]
  • 10
  • [ 5447-38-1 ]
  • [ 10543-12-1 ]
  • 11
  • [ 111-86-4 ]
  • [ 10543-12-1 ]
  • N-octyl-4-acetoxy-3-methoxybenzamide [ No CAS ]
  • 12
  • [ 10543-12-1 ]
  • [ 56681-66-4 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; The obtained <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> was reacted with SOCl2 to prepare 4-acetoxy-3-methoxybenzoyl chloride.
With thionyl chloride; In benzene; for 1h;Reflux; The above compound was suspended in 50 ml dry benzene and 10 ml of thionyl chloride was added. The mixture was refluxed for one hour. The solvent was removed from the solution by rotary evaporation, 20 ml more benzene was added, and again the solvent removed. Finally, the residue was dried on a vacuum line to obtain a light brown semisolid. This moisture-sensitive acid chloride was used in the coupling reaction.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h;Inert atmosphere; Reflux; General procedure: In a one-necked 50-mL round-bottom flask equipped with a magnetic stirring bar, the corresponding carboxylic acid 8, 9 or 10 (11.55 mmol) was placed in CH2Cl2 (10 mL). Subsequently, addition was made of a drop of DMF and oxalyl chloride (4 mL, 47 mmol) in one portion. A vigorous gas emission was immediately released. Stirring was continued until the gas emission stopped (about 25-30 min), and then the mixture was heated to reflux for 1 h. The solvent and excess oxalyl chloride were removed under reduced pressure to furnish the corresponding acid chloride as a dark-brown syrup. The syrup was used in the next step without further purification.
35.6 g With thionyl chloride; In toluene; for 2h;Heating; 40g of <strong>[10543-12-1]3-methoxy-4-acetoxybenzoic acid</strong> and 200g of toluene were added to the reaction flask.31.2 g of sulfoxide was added.The mixture was stirred with heating for 2 h, and then concentrated to dryness under reduced pressure to obtain 35.6 g of 3-methoxy-4-acetoxybenzoyl chloride.

  • 13
  • [ 90826-61-2 ]
  • [ 10543-12-1 ]
  • [ 58534-64-8 ]
  • 14
  • [ 90826-61-2 ]
  • [ 10543-12-1 ]
  • [ 90826-60-1 ]
  • 15
  • 1-(2,6-diacetoxyphenyl)-9-(4-acetoxy-3-methoxyphenyl)nonan-1-one [ No CAS ]
  • [ 10543-12-1 ]
  • 16
  • [ 10543-12-1 ]
  • [ 41690-67-9 ]
  • 4-Acetoxy-3-methoxy-benzoic acid (3R,3aS,4S,8aR)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydro-azulen-4-yl ester [ No CAS ]
  • 17
  • [ 10543-12-1 ]
  • [ 54526-95-3 ]
  • 18
  • [ 10543-12-1 ]
  • 2-(4-acetoxy-3-methoxy-benzoylamino)-4,5-dimethoxy-benzoic acid ethyl ester [ No CAS ]
  • 19
  • [ 10543-12-1 ]
  • 2'-deoxy-2'-(3-methoxy-4-hydroxybenzamido)adenosine [ No CAS ]
  • 20
  • [ 10543-12-1 ]
  • [ 1053710-82-9 ]
  • 21
  • [ 10543-12-1 ]
  • [ 218923-40-1 ]
  • 22
  • [ 10543-12-1 ]
  • 2-(4-hydroxy-3-methoxyphenyl)-3-carbamoylchromone [ No CAS ]
  • 23
  • [ 10543-12-1 ]
  • 2-iodophenyl-4-acetoxy-3-methoxybenzoate [ No CAS ]
  • 24
  • [ 10543-12-1 ]
  • 2-(4-acetoxy-3-methoxyphenyl)-3-carbamoylchromone [ No CAS ]
  • 25
  • [ 10543-12-1 ]
  • [ 169693-78-1 ]
  • 26
  • [ 10543-12-1 ]
  • [ 169693-79-2 ]
  • 27
  • 1-(2',6'-dihydroxyxyphenyl)-9-(4''-hydroxy-3''-methoxyphenyl)nonan-1-one [ No CAS ]
  • [ 10543-12-1 ]
  • 36
  • [ 10543-12-1 ]
  • [ 122892-46-0 ]
  • 37
  • [ 10543-12-1 ]
  • Acetic acid 4-[4-(2-dimethylamino-ethoxy)-benzylcarbamoyl]-2-methoxy-phenyl ester [ No CAS ]
  • 42
  • [ 10543-12-1 ]
  • [ 68985-14-8 ]
  • 43
  • [ 2150-38-1 ]
  • [ 10543-12-1 ]
  • 44
  • [ 93-07-2 ]
  • [ 10543-12-1 ]
  • 46
  • [ 79-37-8 ]
  • [ 10543-12-1 ]
  • [ 56681-66-4 ]
YieldReaction ConditionsOperation in experiment
103% In CH2Cl2 (under a CaSO4 drying tube); a) 4-(Chlorocarbonyl)-2-methoxyphenyl acetate To a stirred suspension of 1.00 g (4.76 mmol) of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> (Pfaltz and Bauer, Inc.) in 4 mL of anhyd CH2Cl2 (under a CaSO4 drying tube) was added 4.15 mL (47.6 mmol) of oxalyl chloride followed by 25 muL of anhyd DMF. After stirring for 4 h at room temperature, the mixture was concentrated in vacuo to afford the title compound as light yellow crystals (1.12 g, 103%). 1H-NMR (300 MHz, CDCl3) delta7.81 (dd, 1 H, J=8.4, 2.1 Hz), 7.66 (d, 1 H, 2.1 Hz), 7.19 (d, 1 H, 8.4 Hz), 3.91 (s, 3 H), and 2.35 (s, 3 H).
103% In CH2Cl2 (under a CaSO4 drying tube); a) 4-(Chlorocarbonyl)-2-methoxyphenyl acetate To a stirred suspension of 1.00 g (4.76 mmol) of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> (Pfaltz and Bauer, Inc.) in 4 mL of anhyd CH2Cl2 (under a CaSO4 drying tube) was added 4.15 mL (47.6 mmol) of oxalyl chloride followed by 25 mL of anhyd DMF. After stirring for 4 h at room temperature, the mixture was concentrated in vacuo to afford the title compound as light yellow crystals (1.12 g, 103%). 1H-NMR (300 MHz, CDCl3) delta 7.81 (dd, 1H, J=8.4, 2.1 Hz), 7.66 (d, 1H, 2.1 Hz), 7.19 (d, 1H, 8.4 Hz), 3.91 (s, 3H), and 2.35 (s, 3H).
  • 47
  • [ 915720-00-2 ]
  • [ 10543-12-1 ]
  • [ 1134111-84-4 ]
  • 48
  • [ 10543-12-1 ]
  • [ 1349175-50-3 ]
  • 49
  • [ 10543-12-1 ]
  • [ 501-65-5 ]
  • [ 1431884-50-2 ]
  • 51
  • [ 10543-12-1 ]
  • [ 74162-07-5 ]
  • 52
  • [ 10543-12-1 ]
  • [ 108128-31-0 ]
  • 53
  • [ 10543-12-1 ]
  • [ 1292298-90-8 ]
  • 56
  • [ 122186-40-7 ]
  • [ 10543-12-1 ]
  • [ 1590385-32-2 ]
YieldReaction ConditionsOperation in experiment
66% With pyridine; In chloroform; at 20℃; for 24h; General procedure: To a solution of glycoside 2,3, or 4 (0.2mmol) in 1mL CHCl3, 0.22mmol of acyl chloride and 0.26mmol of pyridine were added. The reaction mixture was kept at room temperature for 24h and diluted with 20mL CHCl3. The solution was washed with 0.1M H2SO4, satd Na2CO3, water, dried over Na2SO4 and evaporated. The residue was recrystallized from ethanol. 3.5.2 2-(2,3,4,6-Tetra-O-acetyl-beta-d-glucopyranosyloxy)-benzyl (3-methoxy-4-acetoxy) benzoate (8) The compound 8 was obtained from 3-methoxy-4-acetoxy benzoic acid and glycoside 3. Yield 66%, mp 122-124C. UV lambdamax (EtOH)/nm: 242, 291. IR (KBr, numax/cm-1): 2950, 1740, 1600, 1370, 1240, 1050, 1040, 910, 750. 1H NMR (CDCl3, 300MHz) delta: 2.03, 2.05, 2.07, 2.34 (s, 5×3H, Ac), 3.88 (m, 1, -5?), 3.88 (s, 3H, OCH3), 4.16 (dd, 1, J=2.1, 12,0Hz, -6?b), 4.26 (dd, 1, J=5.1, 12.3Hz, H-6?a), 5.09 (d, 1, J=7.5Hz H-1?), 5.14 (m, 1, H-4?), 5.25-5.44 (m, 2, H-2?, -3?), 5.30 (m, 2H, H-7), 7.08 (m, 3H, H-2, H-4, H-13), 7.26 (m, 1, -3), 7.39 (d, 1, J=6.9Hz, -5), 7.68 (s, 1H, H-10), 7.68 (dd, 1H, J=1.2, 9.0Hz, H-14). 13C NMR (CDCl3, 75.5MHz) delta: 20.6 (5×C3, Ac), 56.2 (OCH3), 61.6 (C2, C6?), 61.9 (CH2, C-7), 68.3 (C, C-4?), 71.0 (C, C-2?), 72.1 (C, C-3?), 72.7 (C, C-5?), 99.5 (C, C-1?), 113.6 (CH, C-10), 115.9 (CH, C-2), 122.7 (C, C-4), 122.8 (CH, C-13), 123.7 (CH, C-14), 126.4 (CH, C-6), 128.9 (C, C-9), 129.3 (C, C-5), 129.4 (CH, C-3), 143.7 (C, C-12), 151.1 (C, C-11), 154.5 (C, C-1), 165.6 (C=O, C-8), 168.5, 169.3, 169.4, 170.2, 170.6 (5×C=O, Ac). Anal. Calcd for C31H34O15: C, 57.58; H, 5.30. Found: C, 57.40; H, 5.55
  • 57
  • [ 122186-40-7 ]
  • [ 10543-12-1 ]
  • [ 1590385-41-3 ]
  • 58
  • [ 10543-12-1 ]
  • 2-methoxy-4-[5-(2-phenylethyl)furan-2-yl]carbonyl}phenyl acetate [ No CAS ]
  • 59
  • [ 10543-12-1 ]
  • 2-methoxy-4-[5-(2-phenylethyl)furan-2-yl]methyl}phenyl acetate [ No CAS ]
  • 60
  • [ 10543-12-1 ]
  • [ 1041740-13-9 ]
  • 61
  • [ 121-33-5 ]
  • [ 10543-12-1 ]
  • 62
  • [ 1135-24-6 ]
  • [ 10543-12-1 ]
  • 63
  • C12H12O8 [ No CAS ]
  • [ 10543-12-1 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; In water; at 15 - 95℃; for 3h; A thermometer, a condenser, stirrer, and four-necked flask 100mL equipped with a inlet line for ozone / oxygen mixed gas obtained by the above 3-methoxy-4-acetoxy-cinnamic acid 0.59g (2.4mmol), acetic acid 27g, was charged with water 3.0g, stirring at 0 ~ 10C , 1 hour and 10 minutes the ozone concentration of 4% to 5% oxygen gas at a rate of about 40mL / minute It was blown degree. After completion of the reaction, it was vented over 15 minutes oxygen only to remove the residual ozone in the system. Then, 30-35% aqueous hydrogen peroxide 1.9g at 15 ~ 25C addition, liquid 0.5 hours after heating at a temperature 60 ~ 70C , 2.5 hours at a liquid temperature of 85 ~ 95 heating did. After the reaction, the reaction solution is cooled to room temperature, the yield HPLC analysis by 3-methoxy-4-to calculate acetoxybenzene benzoic acid and yield of 40%, 3-methoxy-4-hydroxy benzoic acid yield of 15%, a total yield is 55%
  • 64
  • [ 10543-12-1 ]
  • C22H24O8 [ No CAS ]
  • 65
  • [ 10543-12-1 ]
  • C28H28O10 [ No CAS ]
  • 66
  • [ 556-48-9 ]
  • [ 10543-12-1 ]
  • C26H28O10 [ No CAS ]
  • 67
  • C8H14O4 [ No CAS ]
  • [ 108-24-7 ]
  • [ 10543-12-1 ]
YieldReaction ConditionsOperation in experiment
24.2 g With sulfuric acid; acetic acid; at 70℃; for 3h; A four-necked flask equipped with a thermometer, a stirrer and a cooling apparatus was charged with 20.0 g (0.12 mol) of the compound represented by the formula (I-12a), 18.2 g (0.18 mol) of acetic anhydride, 100 mL of acetic acid and 5 g of concentrated sulfuric acid were added and the mixture was heated and stirred at 70 C. for 3 hours. After cooling down, 300 mL of water was added while stirring, and the precipitated solid was filtered. After washing with water and drying, 24.2 g (0.12 mol) of a compound represented by the formula (I-12b) was obtained.
  • 68
  • [ 10543-12-1 ]
  • C38H46O12 [ No CAS ]
  • 69
  • [ 10543-12-1 ]
  • C21H22O7 [ No CAS ]
  • 70
  • [ 10543-12-1 ]
  • C35H42O11 [ No CAS ]
  • 71
  • [ 20601-38-1 ]
  • [ 10543-12-1 ]
  • C31H36O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.5 g With dmap; diisopropyl-carbodiimide; In dichloromethane; at 15 - 20℃; for 5h; In a four-necked flask equipped with a thermometer, a stirrer and a dropping funnel, 24.2 g (0.12 mol) of a compound represented by the formula (I-12b)11.8 g (0.059 mol) of the compound represented by the formula (I-12c) and 1.42 g (12 mmol) of N, N-dimethylaminopyridine were taken and suspended in 100 mL of dichloromethane. While ice-cooling, 18.0 g (0.14 mol) of N, N'-diisopropylcarbodiimide was added dropwise so that the reaction temperature did not exceed 15 degrees. After completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. The precipitate was removed by filtration and then the solvent was distilled off. The residue was purified by column chromatography using a mixed solvent of dichloromethane / hexane. Recrystallization with dichloromethane / hexane gave 29.5 g (0.051 mol) of the compound of the formula (I-12 d).
  • 72
  • [ 10543-12-1 ]
  • C15H18O5 [ No CAS ]
  • C25H26O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.3 g With dmap; diisopropyl-carbodiimide; In dichloromethane; at 15 - 20℃; for 5h; In a four-necked flask equipped with a thermometer, a stirrer and a dropping funnel, 27.6 g (0.099 mol) of the compound represented by the formula (I-39 d), the compound represented by the formula (I-12 b) 8 g (0.099 mol) of N, N-dimethylaminopyridine, 1.21 g (9.9 mmol) were taken and suspended in 150 mL of dichloromethane. While ice-cooling, 15.0 g (0.12 mol) of N, N'-diisopropylcarbodiimide was added dropwise so that the reaction temperature did not exceed 15 degrees. After completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. The precipitate was removed by filtration and then the solvent was distilled off. After purification by column chromatography, recrystallization was carried out to obtain 37.3 g (0.079 mol) of a compound represented by the formula (I-39e).
  • 73
  • [ 121-34-6 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 10543-12-1 ]
YieldReaction ConditionsOperation in experiment
203 g With sulfuric acid; at 60℃; for 9h; To a flask equipped with a stirrer, (1.2 mol) of 4-hydroxy-3-methoxybenzoic acid (compound represented by the formula (A-1)) was added to the reaction vessel of the cooler and the thermometer, Acetic acid 700mL, Acetic anhydride (133 g), 1.3 mol (1.3 mol) Sulfuric acid 3g, heated to 60 C reaction for 9 hours. To the reaction solution was added water 1 L, After stirring for 2 hours while cooling with ice, The precipitated solids are filtered. The resulting solid was washed with water and washed with 1 L of water. By drying the solid, 203 g of the compound represented by the formula (A-2) was obtained.
  • 74
  • [ 10543-12-1 ]
  • C33H30O8 [ No CAS ]
  • 75
  • [ 10543-12-1 ]
  • C15H14O4 [ No CAS ]
  • 76
  • [ 10543-12-1 ]
  • C32H28O8 [ No CAS ]
  • 77
  • [ 10543-12-1 ]
  • C15H10FNO4 [ No CAS ]
  • 78
  • [ 10543-12-1 ]
  • C32H24FNO8 [ No CAS ]
  • 79
  • [ 10543-12-1 ]
  • C16H16O4 [ No CAS ]
  • 80
  • [ 10543-12-1 ]
  • C37H27ClO6 [ No CAS ]
  • 81
  • [ 10543-12-1 ]
  • C54H41ClO10 [ No CAS ]
  • 82
  • [ 10543-12-1 ]
  • C29H21ClO3 [ No CAS ]
  • C39H29ClO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
13.7 g With dmap; diisopropyl-carbodiimide; In dichloromethane; at 15 - 20℃; for 6h; To a reaction vessel equipped with a stirrer and a thermometer, the compound of formula (AB-8)12.0 g (0.026 mol) of the compound represented by the formula<strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong>, 5.56 g (0.026 mol)N, N-dimethylaminopyridine (0.32 g, 2.6 mmol) and dichloromethane (50 mL)And stirred while cooling with ice.And 4.0 g (0.032 mol) of N, N'-diisopropylcarbodiimide was added dropwise while maintaining the temperature of the reaction solution at 15 C or less.After the dropwise addition,And the mixture was stirred at room temperature for 6 hours to carry out the reaction.After the reaction solution was filtered and the precipitate was removed,The solvent was distilled off.The resulting solid was dissolved in dichloromethane,After purification by column chromatography,After two recrystallization from a mixed solvent of dichloromethane and methanol,And the compound 13.78 represented by the formula (AB-9) was obtained by drying.
  • 83
  • [ 10543-12-1 ]
  • [ 105-67-9 ]
  • C18H18O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29 g With dmap; diisopropyl-carbodiimide; In dichloromethane; at 15 - 20℃; for 5h; 25.0 g (0.12 mol) of the compound represented by the formula (A-2) was added to a reaction vessel equipped with a stirrer and a thermometer,2,4-dimethylphenol (13.2 g, 0.11 mol)N, N-dimethylaminopyridine (DMAP), 0.7 g (5.4 mmol)Dichloromethane (125 mL), and the mixture was stirred while being cooled with ice.16.4 g (0.13 mol) of N, N'-diisopropylcarbodiimide (DIC) was added dropwise while maintaining the temperature of the reaction solution at 15 C or lower. After the dropwise addition,And the mixture was stirred at room temperature for 5 hours to carry out the reaction. After the reaction solution was filtered and the precipitate was removed, The solvent was distilled off. The resulting solid was dissolved in dichloromethane, And purified by column chromatography (eluent: baby gel 33 g,Eluent: dichloromethane (264 mL) was subjected to purification, The solvent was distilled off. The resulting solid was washed with 102 mL of methanol and then dried to obtain 29.0 g of the compound represented by the formula (A-3).
  • 84
  • [ 106-44-5 ]
  • [ 10543-12-1 ]
  • C17H16O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.8 g With dmap; In dichloromethane; at 15 - 20℃; for 8h; To the reaction vessel equipped with a stirrer and a thermometer, 30.0 g (0.14 mol) of the compound represented by the formula (A-2), 14.0 g (0.13 mol) of p-cresol,N, N-dimethylaminopyridine (0.8 g, 6.5 mmol)Dichloromethane 150 mL,And stirred while cooling with ice.19.7 g (0.16 mol) of N, N'i diisopropylcarbodiimide was added dropwise while maintaining the temperature of the reaction solution at 15 C or lower.After the dropwise addition,And the mixture was stirred at room temperature for 8 hours to carry out the reaction.After the reaction solution was filtered and the precipitate was removed,The solvent was distilled off.The resulting solid was dissolved in dichloromethane,The residue was purified by column chromatography (eluent: silica gel 39 g,Eluent: dichloromethane (312 mL) was subjected to purification,The solvent was distilled off. The resulting solid was subjected to dispersion washing with 117 mL of methanol,And dried to obtain 35.8 g of the compound represented by the formula (B-1).
  • 85
  • [ 10543-12-1 ]
  • [ 82380-18-5 ]
  • C17H12FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
39 g With dmap; diisopropyl-carbodiimide; In dichloromethane; at 15 - 20℃; for 5h; To the reaction vessel equipped with a stirrer and a thermometer, 30.0 g (0.14 mol) of the compound represented by the formula (A-2), 17.8 g (0.13 mol) of <strong>[82380-18-5]4-cyano-3-fluorophenol</strong>, N, N-dimethylaminopyridine (0.8 g, 6.5 mmol) and dichloromethane (150 mL), and the mixture was stirred with ice. The reaction was carried out while maintaining the temperature of the reaction solution at 15 C or less while dropping N,N'-diisopropylcarbodiimide (19.7 g, 0.16 mol). After completion of the dropwise addition, the reaction was carried out by stirring at room temperature for 5 hours. After the reaction solution was filtered and the precipitate was removed, the solvent was distilled off. The obtained solid was dissolved in methylene chloride and purified by column chromatography (refined solvent: 31 g of silica gel, eluent: dichloromethane 248 mL), and the solvent was evaporated. The resulting solid was subjected to dispersion washing with 124 mL of methanol, and dried to obtain 39.0 g of the compound represented by the formula (H-1).
  • 86
  • [ 10543-12-1 ]
  • 4,5,6,7-tetrahydrothieno[3.2-c]pyridine hydrochloride [ No CAS ]
  • (6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(4-hydroxy-3-methoxyphenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.9% 0.5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, andthe mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours whilemaintaining the temperature at 0 to 10C, and 10 ml of purified water was added for layer separation. The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated, added with 10mL of DCM, cooled to 0C, and 0.4 g of 4,5,6,7-tetrahydrothieno[3,2,c]pyridine hydrochloride was added. 0.5 mL of TEAwas added dropwise while maintaining the temperature at 0C, the temperature was gradually raised to room temperature,and the mixture was stirred for 2 hours. DCM phase was concentrated and 10 mL of EtOAC and 10 mL of purified waterwere added for layer separation. The aqueous layer was further extracted with 10 mL of EtOAc, the aqueous layer wasdiscarded, and the organic layer was concentrated. 5 mL of MeOH, 5 mL of purified water and 3.3 mL of TEA wereadded to the concentrate, and the mixture was refluxed for 4 hours. The MeOH phase was concentrated, and the resultingsolid was filtered and washed with purified water to obtain 0.55 g of the title compound as a white solid.Yield: 79.9%1H NMR (400MHz, DMSO-d6) delta 9.48 (s, 1H), 7.35 (d, J = 4.4 Hz, 1H), 7.01 (d, J = 1.6 Hz, 1H), 6.93?6.90(m, 2H), 6.83(d, J = 8.0 Hz, 1H), 4.60(s, 1H), 3.79(s, 3H), 3.74(brs, 2H), 2.88 (t, J = 4.8 Hz, 2H)
  • 87
  • [ 118-71-8 ]
  • [ 10543-12-1 ]
  • 2-methyl-4-oxo-4H-pyran-3-yl 4-hydroxy-3-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.2% 0.5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, andthe mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours whilemaintaining the temperature at 0 to 10C, and 10 ml of purified water was added thereto, followed by layer separation.The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated,10 mL of DCM was added, cooled to 0C, and 0.27 g of maltol was added. 0.5 mL of TEA was added dropwise whilemaintaining the temperature at 0C, the temperature was gradually raised to room temperature, and the mixture wasstirred for 2 hours. DCM was concentrated and 10 mL of EtOAC and 10 mL of purified water were added, followed bylayer separation. The aqueous layer was extracted with 10 mL of EtOAc, the aqueous layer was discarded, and theorganic layer was concentrated. 5 mL of MeOH, 5 mL of purified water and 3.3 mL of TEA were added to the concentrate,and the mixture was refluxed for 4 hours. The MeOH was concentrated, and the resulting solid was filtered and washedwith purified water to obtain 0.35 g of the title compound as a white solid.Yield: 53.2%1H NMR (400MHz, DMSO-d6) delta 10.24 (s, 1H), 8.21 (d, J = 5.6 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 7.53(s, 1H), 6.95 (d, J= 8.0 Hz, 1H), 6.48 (d, J = 5.6 Hz, 1H), 3.85(s, 3H), 2.83(s, 3H)
  • 88
  • [ 10543-12-1 ]
  • [ 54060-30-9 ]
  • N-(3-ethynylphenyl)-4-hydroxy-3-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.2% 0.5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, andthe mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours whilemaintaining the temperature at 0 to 10C, and 10 ml of purified water was added thereto, followed by layer separation.The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated,10 mL of DCM was added, cooled to 0C, and 0.25 g of 3-aminophenylacetylene was added. 0.5 mL of TEA was addeddropwise while maintaining the temperature at 0C, the temperature was gradually raised to room temperature, and themixture was stirred for 2 hours. DCM was concentrated and 10 mL of EtOAC and 10 mL of purified water were added,followed by layer separation. The aqueous layer was extracted with 10 mL of EtOAc, the aqueous layer was discarded,and the organic layer was concentrated. 5 mL of MeOH, 5 mL of purified water and 3.3 mL of TEA were added to theconcentrate, and the mixture was refluxed for 4 hours. The MeOH was concentrated, 10 mL of EtOAc and 10 mL ofpurified water were added, and the layers were separated. The organic layer was distilled under reduced pressure. Tothe resulting solid was added a small amount of IPA and stirred to obtain 0.30 g of the title compound as a white solid.Yield: 47.2%1H NMR (400MHz, DMSO-d6) delta 10.07 (s, 1H), 9.75(brs, 1H), 7.92 (d, J = 1.2 Hz, 1H), 7.80 (dd, J = 1.2 and 8.4 Hz, 1H),7.54?7.50(m, 2H), 7.36 (t, J = 8.0 Hz, 1H), 7.10 (dd, J = 1.2 and 8.0 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 4.18(s, 1H), 3.87(s, 3H)
  • 89
  • [ 4940-11-8 ]
  • [ 10543-12-1 ]
  • 2-ethyl-4-oxo-4H-pyran-3-yl-ester-4-hydroxy-3-methoxy-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.2% 0.5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, and the mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours while maintaining the temperature at 0 to 10C, and 10 ml of purified water was added thereto, followed by layer separation. The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated, 10 mL of DCM was added, cooled to 0C, and 0.31 g of ethylmaltol was added. 0.5 mL of TEA was added dropwise while maintaining the temperature at 0C, the temperature was gradually raised to room temperature, and the mixture was stirred for 2 hours. DCM was concentrated and 10 mL of EtOAC and 10 mL of purified water were added, followed by layer separation. The aqueous layer was extracted with 10 mL of EtOAc, the aqueous layer was discarded, and the organic layer was concentrated. 5 mL of MeOH, MeOH, 5 mL of purified water and 3.3 mL of TEA were added to the concentrate, and the mixture was refluxed for 4 hours. The MeOH was concentrated, 10 mL of EtOAc and 10 mL of purified water were added, and the layers were separated. The organic layer was distilled under reduced pressure and purified by flash column chromatography to obtain 0.34 g of the title compound as a white solid. Yield: 49.2% 1H NMR (400MHz, DMSO-d6) delta 10.24 (s, 1H), 8.23 (d, J = 5.2 Hz, 1H), 7.63 (d, J = 7.6 Hz, 1H), 7.53(s, 1H), 6.95 (d, J = 8.0 Hz, 1H), 6.48 (d, J = 5.6 Hz, 1H), 3.85(s, 3H), 2.62 (q, J = 6.8 Hz, 2H), 1.15 (t, J = 7.2 Hz, 3H)
  • 90
  • [ 10543-12-1 ]
  • [ 96-96-8 ]
  • 4-hydroxy-3-methoxy-N-(4-methoxy-2-nitrophenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.3% 0.5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, and the mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours while maintaining the temperature at 0 to 10C, and 10 ml of purified water was added thereto, followed by layer separation. The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated, 10 mL of DCM was added, cooled to 0C, and 0.40 g of 4-methoxy-2-nitroaniline was added. 0.5 mL of TEA was added dropwise while maintaining the temperature at 0C, the temperature was gradually raised to room temperature, and the mixture was stirred for 2 hours. DCM was concentrated and 10 mL of EtOAC and 10 mL of purified water were added, followed by layer separation. The aqueous layer was extracted with 10 mL of EtOAc, the aqueous layer was discarded, and the organic layer was concentrated. 5 mL of MeOH, 5 mL of purified water and 3.3 mL of TEA were added to the concentrate, and the mixture was refluxed for 4 hours. The MeOH was concentrated, 10 mL of EtOAc and 10 mL of purified water were added, and the layers were separated. The organic layer was distilled under reduced pressure and purified by flash column chromatography to obtain 0.54 g of the title compound as a red solid. Yield: 71.3% 1H NMR(400MHz, DMSO-d6) 10.32(s, 1H), 9.81(brs, 1H)7.63(d, J=8.8, 1H), 7.52?7.46(m, 3H), 7.35(dd, J=2.8 and 8.8, 1H), 3.86(s, 1H), 3.85(s, 3H)
  • 91
  • [ 284462-37-9 ]
  • [ 10543-12-1 ]
  • 4-(4-(4-hydroxy-3-methoxybenzamido)phenoxy)-N-methylpicolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51.3% .5 g of <strong>[10543-12-1]4-acetoxy-3-methoxybenzoic acid</strong> obtained in Preparation Example 2 was added to DCM 10 mL, and the mixture was stirred at 10C. 0.74 g of PCl5 was added at 10C or lower, the mixture was stirred for 2 hours while maintaining the temperature at 0 to 10C, and 10 ml of purified water was added thereto, followed by layer separation. The aqueous layer was discarded and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated, 10 mL of DCM was added, cooled to 0C, and 0.55 g of 4-(4-aminophenoxy)-N-methylpicolinamide was added. 0.5 mL of TEA was added dropwise while maintaining the temperature at 0C, the temperature was gradually raised to room temperature, and the mixture was stirred for 2 hours. DCM was concentrated and 10 mL of EtOAC and 10 mL of purified water were added, followed by layer separation. The aqueous layer was extracted with 10 mL of EtOAc, the aqueous layer was discarded, and the organic layer was concentrated. 5 mL of MeOH, 5 mL of purified water and 3.3 mL of TEA were added to the concentrate, and the mixture was refluxed for 4 hours. The MeOH was concentrated, 10 mL of EtOAc and 10 mL of purified water were added, and the layers were separated. The organic layer was distilled under reduced pressure and purified by flash column chromatography to obtain 0.48 g of the title compound as a light yellow solid. Yield: 51.3% 1H NMR(400MHz, CDCl3) 8.60(s, 1H), 8.39(d, J=5.6, 1H), 8.10(q, J=5.2, 1H), 7.71?7.65(m, 3H), 7.52(d, J=2.0, 1H), 7.43(dd, J=2.0 and 8.4, 1H), 7.04?6.90(m, 4H), 6.73(brs, 1H), 3.78(s, 3H), 3.01(d, J=5.2, 3H)
  • 92
  • [ 10543-12-1 ]
  • (E)-3-(2-(4-acetoxy-3-methoxyphenyl)-7-methoxybenzofuran-5-yl)allyl acetate [ No CAS ]
  • 93
  • [ 10543-12-1 ]
  • (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran [ No CAS ]
  • 94
  • [ 10543-12-1 ]
  • 4-(5-allyl-7-methoxybenzofuran-2-yl)-2-methoxyphenyl acetate [ No CAS ]
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