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[ CAS No. 524-12-9 ] {[proInfo.proName]}

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Chemical Structure| 524-12-9
Chemical Structure| 524-12-9
Structure of 524-12-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 524-12-9 ]

CAS No. :524-12-9 MDL No. :MFCD07778564
Formula : C16H10O7 Boiling Point : -
Linear Structure Formula :- InChI Key :XQDCKJKKMFWXGB-UHFFFAOYSA-N
M.W : 314.25 Pubchem ID :5281813
Synonyms :
IKK Inhibitor II

Calculated chemistry of [ 524-12-9 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.06
Num. rotatable bonds : 1
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 82.32
TPSA : 113.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 0.93
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 2.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.77
Solubility : 0.0535 mg/ml ; 0.00017 mol/l
Class : Soluble
Log S (Ali) : -4.4
Solubility : 0.0125 mg/ml ; 0.0000398 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.56
Solubility : 0.00862 mg/ml ; 0.0000274 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.29

Safety of [ 524-12-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 524-12-9 ]

* 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 [ 524-12-9 ]

[ 524-12-9 ] Synthesis Path-Downstream   1~44

  • 1
  • [ 524-12-9 ]
  • [ 100-44-7 ]
  • [ 115623-32-0 ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate In N,N-dimethyl-formamide for 0.833333h; Heating;
  • 2
  • [ 67964-24-3 ]
  • [ 120-80-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
25% With sodium acetate; potassium hexacyanoferrate(III) In water; acetone for 2h; Ambient temperature;
With ascorbic acid 1.) tyrosinase, pH=6.8, r.t., 1 h; Yield given. Multistep reaction;
  • 3
  • [ 115623-32-0 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogen In 1,4-dioxane 2nd step of purification of 9 (wedelolactone);
81% With boron trichloride In dichloromethane at 0℃; Inert atmosphere; Preparation of WEL 5 To a solution of 17 (0.58 g, 1.0 mmol) in DCM (15 mL) was added BCl3(3 mL, 1 M) slowly at 0 C under Ar atmosphere. After the reaction was finished, the mixture wasconcentrated and then purified by column chromatography (MeOH:DCM = 1:20) to give the product 5.Gray solid; 254 mg, 81% yield; m.p. >300 C; Rf: 0.48 (MeOH:DCM = 1:10); IR (cm1): 3397, 2955, 2923,2853, 1710, 1670, 1612, 1447, 1324, 1284, 1206, 1151, 1070, 1047; 1H-NMR (DMSO-d6, 300 MHz): 3.82 (s,3H), 6.45 (d, J = 1.8 Hz, 1H), 6.62 (d, J = 1.9 Hz, 1H), 7.16 (s, 1H), 7.24 (s, 1H); 13C-NMR (DMSO-d6,75 MHz): 55.7, 93.2, 96.7, 98.1, 98.8, 101.7, 104.5, 113.7, 144.3, 145.4, 148.8, 154.8, 155.2, 157.7, 158.9,162.2; HR-MS (ESI) calculated for C16H11O7 [M + H] 315.0505, found 315.0504.
YieldReaction ConditionsOperation in experiment
Tri-O-methylwedelolacton i. Acetanhydrid + HI (115-120grad);
Tri-O-methylwedelolacton /Acetanhydrid, HI, 115-120grad;
Brenzcatechin, 4,5-Dihydroxy-7-methoxy-cumarin, Kaliumhexacyanoferrat (III), Natriumacetat, aq.Aceton, (blaue Lsg. wird rotbraun);
YieldReaction ConditionsOperation in experiment
With hydrogen iodide
  • 6
  • [ 524-12-9 ]
  • [ 75-36-5 ]
  • [ 6468-54-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 25℃; for 2h;
  • 7
  • [ 627489-05-8 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
93% With sulfuric acid; acetic acid In water at 50℃; for 1h;
  • 8
  • [ 5447-02-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 1.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 2.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 3.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 5.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 6.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 7.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 8.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
Multi-step reaction with 8 steps 1.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 1.2: 0.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 20 °C 3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 4.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 10
  • [ 27688-85-3 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 2: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 11
  • [ 91360-58-6 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: t-BuOK / tetrahydrofuran / 0.5 h / 0 °C 1.2: 75 percent / t-BuOK / tetrahydrofuran / 0 - 25 °C 2.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 12
  • [ 139-85-5 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 94 percent / K2CO3; n-Bu4NI / acetone / 24 h / Heating 2.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 2.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 3.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 4.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 5.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 6.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 7.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 8.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 9.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
Multi-step reaction with 9 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 2.2: 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 20 °C 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 5.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 9.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 13
  • [ 627489-10-5 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 14
  • [ 627489-15-0 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 15
  • [ 344303-12-4 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 2: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 3: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 16
  • [ 627489-61-6 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 2: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 3: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 4: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 17
  • [ 344303-15-7 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 2: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C
  • 18
  • [ 108-73-6 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogenchloride / diethyl ether / 2 h 2: hydrogenchloride / 1 h / Heating 3: sodium carbonate / water / 1 h / 80 °C 4: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h
Multi-step reaction with 8 steps 1.1: zinc(II) chloride / 2 h / 100 °C 2.1: potassium carbonate / acetone / 1 h / 90 °C 2.2: 1.5 h / 90 °C 3.1: bromine / dichloromethane / 8 h / 0 - 10 °C 3.2: 1 h / 20 °C 4.1: potassium carbonate / acetone / 56 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 19
  • [ 162888-73-5 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / 1 h / Heating 2: sodium carbonate / water / 1 h / 80 °C 3: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h
  • 20
  • [ 17575-26-7 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / water / 1 h / 80 °C 2: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h
  • 21
  • [ 1023744-97-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
87% With boron trichloride In dichloromethane at 0℃;
  • 22
  • 5-(benzyloxy)-3-(4,5-bis(benzyloxy)-2-((4-methoxybenzyl)oxy)phenyl)-7-methoxy-2-chromenone [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 2: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 23
  • C34H37BO6 [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 24
  • 1,2-dibenzyloxy-4-(p-methoxybenzyl)oxybenzene [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 25
  • 1,2-dibenzyloxy-4-bromo-5-(p-methoxybenzyl)oxybenzene [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 26
  • [ 2732-18-5 ]
  • [ 524-12-9 ]
  • 27
  • [ 21524-17-4 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: bromine / dichloromethane / 8 h / 0 - 10 °C 1.2: 1 h / 20 °C 2.1: potassium carbonate / acetone / 56 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4.1: potassium carbonate / N,N-dimethyl-formamide 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 28
  • [ 1023744-89-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 56 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 29
  • 3-bromo-5-benzyloxy-7-acetoxyl-2-chromenone [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 30
  • 5-(benzyloxy)-3-(4,5-bis(benzyloxy)-2-((4-methoxybenzyl)oxy)phenyl)-7-hydroxy-2-chromenone [ No CAS ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 3: boron trichloride / dichloromethane / 0 °C / Inert atmosphere
  • 31
  • [ 480-66-0 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 0 - 25 °C / Schlenk technique 2: sodium / Heating; Schlenk technique 3: catechol oxidase from Ipomoea batatas (sweet potato) / aq. phosphate buffer / 24 h / 25 °C / pH 7.4 / Schlenk technique; Enzymatic reaction
  • 32
  • [ 524-12-9 ]
  • [ 105-58-8 ]
  • [ 2892089-55-1 ]
YieldReaction ConditionsOperation in experiment
55 % With potassium carbonate In acetone at 0 - 25℃; Schlenk technique;
  • 33
  • [ 524-12-9 ]
  • [ 105-58-8 ]
  • [ 1805-77-2 ]
YieldReaction ConditionsOperation in experiment
52 % With potassium carbonate In acetone at 0 - 25℃; Schlenk technique;
  • 34
  • [ 2925383-80-6 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
71 % With hydrogenchloride In ethanol at 78℃; Wedelolactone (1) Compound 2 (40.00 mg, 0.09 mmol) was dissolved in saturated ethanol hydrochloride (1 mL), and the reaction solution was stirred at 78 °C for 6 h. After completion of the reaction, the reaction mixture was quenched with saturated NaHCO3 and extracted with ethyl acetate (5 mL 3). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, MeOH/DCM = 1:10, v/v) to obtain compound 1 (20 mg, 71%) as a white solid. mp 299-301 °C. IR (νmax, cm-1) ν 3360, 3139, 3037, 2995, 2942, 1786, 1661, 1510, 1458, 1401, 1361, 1248, 1164, 1044; 1HNMR (400 MHz, DMSO-d6) δ 10.97 (s,1H, -OH), 9.43 (s, 1H, -OH),9.38 (s, 1H, -OH), 7.24 (s, 1H, -ArH), 7.17(s, 1H, -ArH), 6.64 (d, J = 2.3 Hz,1H, -ArH), 6.47 (d, J = 2.3 Hz, 1H, -ArH), 3.83 (s, 3H, -CH3); 13C NMR (101 MHz, DMSO) δ 162.7, 159.4 158.2, 155.7, 155.3, 149.3, 145.9, 144.8, 114.2, 105.0, 102.1, 99.3, 98.6, 97.1, 93.7, 56.2. HRMS: m/z calcd for C16H11O7 [M+H]+ 315.0494; found: 315.0497.
  • 35
  • [ 35094-87-2 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrafluoroboric acid diethyl ether / toluene; tetrahydrofuran / 12 h / -78 - 20 °C 1.2: 4 h / 20 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 3.1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 4.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: hydrogenchloride / ethanol / 6 h / 78 °C
  • 36
  • [ 533-73-3 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: aluminum (III) chloride / toluene / 12 h / 0 - 20 °C 2.1: tetrafluoroboric acid diethyl ether / toluene; tetrahydrofuran / 12 h / -78 - 20 °C 2.2: 4 h / 20 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 4.1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 7.1: hydrogenchloride / ethanol / 6 h / 78 °C
  • 37
  • [ 2174-64-3 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one / dichloromethane; 1,4-dioxane / 16 h / 0 °C 2.1: acetyl chloride; zinc dibromide / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 4.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: hydrogenchloride / ethanol / 6 h / 78 °C
  • 38
  • [ 121869-51-0 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetyl chloride; zinc dibromide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 5.1: hydrogenchloride / ethanol / 6 h / 78 °C
  • 39
  • [ 885118-14-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 4: hydrogenchloride / ethanol / 6 h / 78 °C
  • 40
  • [ 2925383-75-9 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 3: hydrogenchloride / ethanol / 6 h / 78 °C
  • 41
  • [ 2925383-76-0 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 2: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 3: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 5: hydrogenchloride / ethanol / 6 h / 78 °C
  • 42
  • [ 2925383-77-1 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 4: hydrogenchloride / ethanol / 6 h / 78 °C
  • 43
  • [ 2925383-78-2 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 3: hydrogenchloride / ethanol / 6 h / 78 °C
  • 44
  • [ 2925383-79-3 ]
  • [ 524-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 2: hydrogenchloride / ethanol / 6 h / 78 °C
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