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[ CAS No. 50671-05-1 ] {[proInfo.proName]}

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Chemical Structure| 50671-05-1
Chemical Structure| 50671-05-1
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Product Details of [ 50671-05-1 ]

CAS No. :50671-05-1 MDL No. :MFCD03424813
Formula : C11H11BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IFSMFGOJDWUHEW-UHFFFAOYSA-N
M.W : 271.11 Pubchem ID :2757148
Synonyms :

Calculated chemistry of [ 50671-05-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.04
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.216 mg/ml ; 0.000795 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.206 mg/ml ; 0.000761 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0223 mg/ml ; 0.0000824 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.94

Safety of [ 50671-05-1 ]

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

Application In Synthesis of [ 50671-05-1 ]

* 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 [ 50671-05-1 ]

[ 50671-05-1 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 50671-05-1 ]
  • [ 2142-69-0 ]
  • 2
  • [ 141-97-9 ]
  • [ 7154-66-7 ]
  • [ 50671-05-1 ]
  • 3
  • [ 50671-05-1 ]
  • [ 50671-00-6 ]
  • [ 50670-86-5 ]
  • 6
  • [ 136918-14-4 ]
  • [ 50671-05-1 ]
  • [ 143583-69-1 ]
  • [ 83665-31-0 ]
  • 5,11-Dioxo-5,11-dihydro-isoindolo[2,1-a]quinoline-6-carboxylic acid ethyl ester [ No CAS ]
  • 7
  • [ 623-73-4 ]
  • [ 6630-33-7 ]
  • [ 50671-05-1 ]
  • 9
  • [ 2042-37-7 ]
  • [ 105-36-2 ]
  • [ 50671-05-1 ]
  • 12
  • [ 50671-05-1 ]
  • [ 708-06-5 ]
  • [ 1148118-34-6 ]
  • 13
  • [ 50671-05-1 ]
  • (1SR,5SR)-ethyl 2-(2-bromophenyl)-3-azabicyclo[3.1.0]hex-2-ene-1-carboxylate [ No CAS ]
  • 15
  • [ 50671-05-1 ]
  • [ 1332622-28-2 ]
  • 16
  • [ 50671-05-1 ]
  • [ 1332622-32-8 ]
  • 17
  • [ 50671-05-1 ]
  • [ 1332622-33-9 ]
  • 18
  • [ 50671-05-1 ]
  • [ 1332622-30-6 ]
  • 19
  • [ 50671-05-1 ]
  • [ 1332622-31-7 ]
  • 20
  • [ 50671-05-1 ]
  • [ 1332622-34-0 ]
  • 21
  • [ 50671-05-1 ]
  • [ 1332622-35-1 ]
  • 22
  • [ 50671-05-1 ]
  • 4-oxo-1-(2-pyridyl)-1,4-dihydroquinoline-3-carboxylic acid sodium salt [ No CAS ]
  • 23
  • [ 50671-05-1 ]
  • 4-oxo-1-(3-pyridyl)-1,4-dihydroquinoline-3-carboxylic acid sodium salt [ No CAS ]
  • 24
  • [ 50671-05-1 ]
  • 4-oxo-1-(4-pyridyl)-1,4-dihydroquinoline-3-carboxylic acid sodium salt [ No CAS ]
  • 25
  • [ 50671-05-1 ]
  • [ 1332622-38-4 ]
  • 26
  • [ 50671-05-1 ]
  • 4-oxo-1-(4-pyridylmethyl)-1,4-dihydroquinoline-3-carboxylic acid sodium salt [ No CAS ]
  • 27
  • [ 50671-05-1 ]
  • [ 1332622-47-5 ]
  • 28
  • [ 50671-05-1 ]
  • [ 1332622-48-6 ]
  • 29
  • [ 50671-05-1 ]
  • [ 4637-24-5 ]
  • [ 311340-72-4 ]
  • 30
  • [ 6148-64-7 ]
  • [ 7154-66-7 ]
  • [ 50671-05-1 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; magnesium chloride; In acetonitrile; at 20℃; Experimental operation: Take malonate potassium salt 1.00g (about 5.47mmol) and anhydrous magnesium chloride was added 0.65g (about 6.84mmol) in 25mL round bottom flask, 0.55g triethylamine was dropped after 6mL dissolved in acetonitrile, stirred at room temperature for 30min. Then dropped by 2mL acetonitrile dissolved 0.48g (2.5mmol) of o-bromobenzoyl chloride 1e, supplemented triethylamine 0.06mL, stirred at room temperature overnight. Post-treatment: 30mL of water was added to dilute the reaction solution, and then were added 30,20,20mL ethyl acetate and the ethyl acetate layer was collected. After washing with saturated brine 30mL ethyl acetate layer was dried over anhydrous sodium sulfate, and spin dry column chromatography (PE: EA = 15: 1) 2e of product obtained is isolated, a yield of 92%
92% Experimental operation: Take malonate potassium salt 1.00 g (about5.47 mmol) of anhydrous magnesium chloride and 0.65 g (about 6.84mmol) in 25 mLround bottom flask, was added dropwise 0.55 g of triethylamine was added after6 mL of acetonitrile was dissolved, followed by stirring at room temperature for30 min.Then dropped by 2 mL of acetonitrile was dissolved 0.48 g (2.5 mmol) o-bromobenzoyl chloride 1e, supplemented with triethylamine 0.06 mL, stirred atroom temperature overnight. After treatment: 30 mL of water was added to dilutethe reaction solution, and then were added 30,20,20 mL ethyl acetate, and theethyl acetate layer was collected. After, 30 mL with saturated brine ethylacetate layer was dried over anhydrous sodium sulfate, and spin dry columnchromatography (PE: EA = 15: 1) to give the product isolated 2e, in 92% yield.
  • 31
  • [ 615-43-0 ]
  • [ 50671-05-1 ]
  • [ 1373169-26-6 ]
  • 32
  • [ 50671-05-1 ]
  • [ 1373169-49-3 ]
  • 33
  • [ 50671-05-1 ]
  • [ 1373169-68-6 ]
  • 34
  • [ 119072-55-8 ]
  • [ 50671-05-1 ]
  • ethyl 1-(tert-butylimino)-3-hydroxy-1H-indene-2-carboxylate [ No CAS ]
  • 35
  • [ 50671-05-1 ]
  • ethyl 3-(2-bromophenyl)-2-diazo-3-oxopropanoate [ No CAS ]
  • 36
  • [ 50671-05-1 ]
  • ethyl 2-(2-bromophenyl)-1-methyl-1H-indole-3-carboxylate [ No CAS ]
  • 37
  • [ 50671-05-1 ]
  • diethyl 2-(2-bromophenyl)-4-hydroxynaphthalene-1,3-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With copper(l) iodide; potassium carbonate; propionic acid; In isopropyl alcohol; at 100℃; for 24h;Sealed tube; Inert atmosphere; Molecular sieve; General procedure: 4.3.1. General procedure II for the CuI-catalyzed synthesis of 2 a-n. An oven-dried 10 mL vial equipped with a magnetic stir barwas charged with CuI (0.05 mmol, 10 mg) and K2CO3 (1 mmol,138 mg). The sealed tube was evacuated and backfilled with argon (two times). Then, them<strong>[50671-05-1]ethyl 3-(2-bromophenyl)-3-oxopropanoate</strong> 1 (1 mmol), propionic acid (22 mg, 0.3 mmol) and freshly distilled isopropanol (2 mL) were added and the reaction mixturewas stirredat 100 C for 24 h. After cooling to room temperature, the reaction mixture was diluted with water (15 mL) and extracted with EtOAc(320 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel to afford the 1-naphthol 2 in analytically pure form.
  • 39
  • [ 610-94-6 ]
  • [ 141-78-6 ]
  • [ 50671-05-1 ]
YieldReaction ConditionsOperation in experiment
71% General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2×50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0C using an ice bath and NaH (60% in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 1.
  • 40
  • [ 50671-05-1 ]
  • C19H15BrO5 [ No CAS ]
  • 41
  • [ 50671-05-1 ]
  • [ 78-94-4 ]
  • C15H17BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Experiment operation: Take 0.452g (2mmol) 2e in 25mL round bottom flask was added 0.16g of sodium ethoxide was dissolved with 10mL ethanol, stirred for fifteen minutes at room temperature, followed by taking 0.162mL (2mmol) -propenone in the flask, stirred at room temperature 2h . Post-treatment: 5% hydrochloric acid was added to dilute the reaction solution, and then were extracted with ethyl 30,20,20mL aqueous phase was washed with saturated brine and good oil layer, spin dried over anhydrous sodium sulfate, column chromatography (the PE: EA = 10: 1) to give the product isolated 3e, yield 85%
85% Experiment operation: take 0.452 g (2 mmol) 2e in 25 mL roundbottom flask, 0.16 g of sodium ethoxide was added after 10 ml ethanol solutionwas added and stirred for 15 minutes at room temperature, followed by taking0.162 mL (2 mmol) in propenone flask, stirred at room temperature 2 h.Post-treatment: 5% hydrochloric acid 30,20,20 mL was added to dilute thereaction solution, and then were extracted with ethyl acetate and the aqueousphase was washed with saturated brine and dried over anhydrous sodium sulfateand purified by spin column chromatography (PE: EA = 10: 1) to give the isolatedproduct 3e, a yield of 85%.
  • 42
  • [ 50671-05-1 ]
  • C24H21BrO5 [ No CAS ]
  • 43
  • [ 50671-05-1 ]
  • C25H25BrO5 [ No CAS ]
  • 44
  • [ 50671-05-1 ]
  • C30H26BrFO5 [ No CAS ]
  • 45
  • [ 50671-05-1 ]
  • C30H27BrO5 [ No CAS ]
  • 46
  • [ 50671-05-1 ]
  • C24H23BrO5 [ No CAS ]
  • 47
  • [ 50671-05-1 ]
  • [ 122-52-1 ]
  • ethyl 3-(2-bromophenyl)-2-(diethoxyphosphoryl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) chloride; dibenzoyl peroxide; In N,N-dimethyl-formamide; at 110℃; In the reaction flask by adding 3 - (2-bromophenyl) - 3- oxo ethyl propionate (0.269g, 1 . 0mmol), triethyl phosphite (1.162g, 7 . 0mmol), cuprous chloride (0.010g, 0 . 1mmol), benzoyl peroxide (1.694g, 7 . 0mmol) and dimethyl formamide (5 ml), 110 C reaction;TLC until the complete end tracking of the reaction;After the reaction the crude product by column chromatography (petroleum ether: ethyl acetate = 4:1), to obtain the target product (yield 79%).
  • 48
  • [ 50671-05-1 ]
  • [ 1761-61-1 ]
  • 6-bromo-3-(2-bromobenzoyl)-2H-chromen-2-one [ No CAS ]
  • 49
  • [ 50671-05-1 ]
  • [ 62123-82-4 ]
  • 50
  • [ 2142-69-0 ]
  • [ 105-58-8 ]
  • [ 50671-05-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In toluene; at 70℃; for 0.333333h;Inert atmosphere; 97.1 o-bromoacetophenone as starting material,2.5 eq of NaH and 2.0 eq of diethyl carbonate were added to the toluene.Heated at 70 C under nitrogen for 20 min.After the reaction,Add cold water to room temperature,Add glacial acetic acid to the system neutral,Extracted with ethyl acetate (50 mL×3).Divide the organic layer,Washed with 10 ml of saturated saline solution,Dry over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure.Crude column chromatography(petroleum ether: ethyl acetate = 40:1)Compound 97-1,O-bromobenzoylacetate;
  • 51
  • [ 50671-05-1 ]
  • ethyl 2-bromo-3-(2-bromophenyl)-3-oxopropanoate [ No CAS ]
  • 52
  • [ 50671-05-1 ]
  • ethyl (E)-3-amino-2-(2-bromobenzoyl)-3-phenylacrylate [ No CAS ]
  • ethyl 3-amino-2-(2-bromobenzoyl)-3-phenylacrylate [ No CAS ]
  • 53
  • [ 50671-05-1 ]
  • [ 130-15-4 ]
  • ethyl 2-(2-bromophenyl)-5-hydroxynaphtho[1,2-b]furan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With zinc(II) iodide; In dichloromethane; at 110℃; for 0.5h;Sealed tube; General procedure: 1,4-naphthoquinone (1.5equiv.) ZnI2 (0.7equiv.) and b-keto esters5 a-n (1.0 equiv.) were dissolved in dry CH2Cl2(6 mL) in a 10mLreaction glass vial containing a tiny stirring magnet The vial wassealed tightly with an aluminium-Teflon crimp top and themixture was irradiated for 30 min at a pre-selected temperature of110 C, with an irradiation power of 60W. After the reaction, thevial was cooled to 50 C by gas jet cooling. The crude mixture wasportioned between CH2Cl2 and saturated solution of sodium chloride(6 mL) and the aqueous layer was extracted with methylenchloride (3 6 mL). The combined organic layer were dried onSodium sulfate anhydrous, filtered and the solvent was removedunder reduce pressure. Then, final crude compounds were purifiedby flash chromatography over silica gel.
  • 54
  • [ 50671-05-1 ]
  • [ 1450828-30-4 ]
YieldReaction ConditionsOperation in experiment
72% With ammonium acetate; acetic acid; In toluene; at 140℃; for 0.333333h;Molecular sieve; Sealed tube; General procedure: b-keto esters 5 a-n (1.0 equiv.), Ammonium acetate (3.0 equiv.)and Acetic acid (drops) were dissolved in dry Toluol (6 mL) in a10 mL reaction glass vial containing a tiny stirring magnet andmolecular sieves. The vial was sealed tightly with an aluminium-Teflon crimp top and the mixture was irradiated for 20 min at apre-selected temperature of 140 C, with an irradiation power of60W. After the reaction, the vial was cooled to 50 C by gas jetcooling. The crude mixture was portioned between ethyl acetateand saturated solution of Sodium bicarbonate (15 mL of each) andthe aqueous layer was extracted with ethyl acetate (3 15 mL). Thecombined organic layer were dried on Sodium sulfate anhydrous,filtered and the solvent was removed under reduce pressure. Then,final crude compounds were purified by flash chromatography oversilica gel.
  • 55
  • [ 50671-05-1 ]
  • ethyl 2-(2-bromophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate [ No CAS ]
  • 56
  • [ 50671-05-1 ]
  • [ 106-51-4 ]
  • C17H13BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) iodide; In dichloromethane; at 110℃; for 0.5h;Sealed tube; Microwave irradiation; General procedure: 1,4-naphthoquinone (1.5equiv.) ZnI2 (0.7equiv.) and b-keto esters5 a-n (1.0 equiv.) were dissolved in dry CH2Cl2(6 mL) in a 10mLreaction glass vial containing a tiny stirring magnet The vial wassealed tightly with an aluminium-Teflon crimp top and themixture was irradiated for 30 min at a pre-selected temperature of110 C, with an irradiation power of 60W. After the reaction, thevial was cooled to 50 C by gas jet cooling. The crude mixture wasportioned between CH2Cl2 and saturated solution of sodium chloride(6 mL) and the aqueous layer was extracted with methylenchloride (3 6 mL). The combined organic layer were dried onSodium sulfate anhydrous, filtered and the solvent was removedunder reduce pressure. Then, final crude compounds were purifiedby flash chromatography over silica gel.
With copper(II) bis(trifluoromethanesulfonate); for 10h;Inert atmosphere; Reflux; 97.2 ethyl o-bromobenzoylacetate,Dissolved in 5% with copper 5% triflate,0.6 eq of 1,4 benzoquinone was slowly added dropwise under nitrogen protection.Heated back to reflux for 10 h,Cool to room temperature.NH4Cl is quenched,Extracted with ethyl acetate (50 mL×3).Divide the organic layer,Washed with 10 ml of saturated saline solution,Dry over anhydrous sodium sulfate,The crude product obtained by evaporation of ethyl acetate was purified by silica gel column chromatography.(Petroleum ether: ethyl acetate = 20:1) Compound 97-2
  • 57
  • [ 50671-05-1 ]
  • ethyl 1-(2-bromobenzoyl)cyclopent-3-ene-1-carboxylate [ No CAS ]
  • 58
  • [ 50671-05-1 ]
  • ethyl (5S,8S)-9-oxo-5,6,7,9-tetrahydro-8H-5,8-methanobenzo[7]annulene-8-carboxylate [ No CAS ]
  • 59
  • [ 50671-05-1 ]
  • [ 106-95-6 ]
  • C17H19BrO3 [ No CAS ]
  • 61
  • [ 6148-64-7 ]
  • [ 7154-66-7 ]
  • [ 50671-05-1 ]
  • [ 119031-48-0 ]
YieldReaction ConditionsOperation in experiment
Ethyl potassium malonate (1 .39 g, 8.2 mmol) was suspended in dry MeCN (22 mL) under a flow of nitrogen, and the mixture was cooled to 10C. Et3N (1.2 mL, 8.6 mmol) and MgCI2 (935 mg, 9.84 mmol) were added and the reaction was stirred at rt for 2 h 30 min. The reaction was once again cooled to 10C and 2-bromobenzoyl chloride (900 mg, 4.1 mmol) followed by further Et3N (1 14 muIota, 0.82 mmol) were added. The mixture was stirred at rt overnight. The reaction was quenched with a saturated NH4CI solution and extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc in cHex to yield the desired product 2A (379 mg, 34%) as a mixture of tautomers, which was used in the following step without further purification. 1H NMR (400MHz, CDCI3) delta 7.63-7.58 (m, 1 H), 7.39-7.21 (m, 2H), 4.16 (q, 2H), 3.99 (s, 2H), 1 .22 (t, 3H) - tautomer 1 , ethyl 3-(2-bromophenyl)-3-oxopropanoate 1H NMR (400MHz, CDCI3) delta 12.40 (s, 1 H), 7.52-7.45 (m, 1 H), 7.39-7.21 (m, 2H), 5.43 (s, 1 H), 4.25 (q, 2H), 3.99 (s, 1 H), 1.31 (t, 3H) - tautomer 2, (Z)-ethyl 3-(2-bromophenyl)-3- hydroxyacrylate MS (ES) C11H11BrO3 requires: 270/272, found: 271/273(M+H), -100%
  • 62
  • [ 50671-05-1 ]
  • C17H15NO4 [ No CAS ]
  • 63
  • [ 50671-05-1 ]
  • [ 1026164-88-4 ]
  • 64
  • [ 50671-05-1 ]
  • 8-hydroxyl-7-(piperidin-1-ylmethyl)benzofurano[3,2-c]quinolin-6(5H)-one [ No CAS ]
  • 65
  • [ 6148-64-7 ]
  • [ 90766-96-4 ]
  • [ 50671-05-1 ]
  • 66
  • [ 50671-05-1 ]
  • 5-(2-bromophenyl)-3H-1,2-dithiole-3-thione [ No CAS ]
  • 67
  • [ 50671-05-1 ]
  • ethyl 4-(2-bromophenyl)-2-(isopropylcarbamoyl)thiazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium formate / ethanol / 20 h / Reflux; Schlenk technique; Inert atmosphere 2: sulfur; caesium carbonate / acetonitrile / 48 h / 90 °C / Inert atmosphere; Schlenk technique
  • 68
  • [ 50671-05-1 ]
  • diethyl 4-(2-bromophenyl)thiazole-2,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium formate / ethanol / 20 h / Reflux; Schlenk technique; Inert atmosphere 2: sulfur; caesium carbonate / acetonitrile / 48 h / 90 °C / Inert atmosphere; Schlenk technique
  • 69
  • [ 50671-05-1 ]
  • diethyl 3-(2-bromophenyl)isothiazole-4,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium formate / ethanol / 20 h / Reflux; Schlenk technique; Inert atmosphere 2: sulfur; 1,10-Phenanthroline; copper; sodium phosphate / acetonitrile / 20 h / 90 °C / Inert atmosphere; Schlenk technique
  • 70
  • [ 50671-05-1 ]
  • [ 107-19-7 ]
  • C12H9BrO3 [ No CAS ]
  • C12H9BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene at 120℃; for 48h; Dean-Stark; Overall yield = 74 percent;
  • 71
  • [ 50671-05-1 ]
  • [ 135774-34-4 ]
YieldReaction ConditionsOperation in experiment
With Candida antarctica lipase B; Selectfluor In aq. phosphate buffer at 50℃; for 12h; Enzymatic reaction;
  • 72
  • [ 50671-05-1 ]
  • 1-(2-bromophenyl)-2-fluoroethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Selectfluor; Candida antarctica lipase B / aq. phosphate buffer / 12 h / 50 °C / pH 7.4 / Enzymatic reaction 2: D-glucose / aq. phosphate buffer / 30 °C / pH 6.5 / Microbiological reaction
  • 73
  • [ 50671-05-1 ]
  • [ 1576-35-8 ]
  • ethyl (E)-3-(2-bromophenyl)-3-(2-tosylhydrazono)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.4 g In toluene at 100℃; for 2h;
  • 74
  • [ 50671-05-1 ]
  • ethyl (4R,4aR,8aR)-3-(2-bromophenyl)-1-tosyl-1,4,4a,7,8,8a-hexahydrocinnoline-4-carboxylate [ No CAS ]
  • ethyl 3-(2-bromophenyl)-1-tosyl-1,4,4a,7,8,8a-hexahydrocinnoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 2 h / 100 °C 2: bis(η3-allyl-μ-chloropalladium(II)); tBu-RuPhos; potassium carbonate / tetrahydrofuran / 36 h / 35 °C / Inert atmosphere; Schlenk technique
  • 75
  • [ 50671-05-1 ]
  • ethyl (Z)-2-(amino(2-bromophenyl)methylene)-4-(triisopropylsilyl)but-3-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium acetate / methanol / Reflux 2: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 1,10-Phenanthroline / acetonitrile / 50 °C
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkyl Halide Occurrence • Alkylation of Aldehydes or Ketones • Alkylation of an Alkynyl Anion • Alkylation of Enolate Ions • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotection of Cbz-Amino Acids • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Ester Cleavage • Ester Hydrolysis • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Methylation of Ammonia • Methylation of Ammonia • Michael Addition • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Strecker Synthesis • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Williamson Ether Syntheses • Wittig Reaction • Wolff-Kishner Reduction
Historical Records

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