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CAS No. : | 1076-26-2 | MDL No. : | MFCD00029266 |
Formula : | C11H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BBOCZFGVXFNCTC-UHFFFAOYSA-N |
M.W : | 158.20 | Pubchem ID : | 95939 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.94 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.01 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 3.18 |
Log Po/w (WLOGP) : | 2.85 |
Log Po/w (MLOGP) : | 2.83 |
Log Po/w (SILICOS-IT) : | 2.98 |
Consensus Log Po/w : | 2.76 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.0573 mg/ml ; 0.000362 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.28 |
Solubility : | 0.0838 mg/ml ; 0.00053 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.87 |
Solubility : | 0.0212 mg/ml ; 0.000134 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tri-n-butyl-tin hydride at 200℃; for 0.5h; | |
With ethanol; nickel Hydrogenation; | ||
With phenylmethanethiol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer In methanol at 20℃; for 12h; Inert atmosphere; regioselective reaction; | |
With ethanol; nickel at 110℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-chloro-succinimide; potassium acetate In water at 20℃; for 0.5h; Green chemistry; | |
92% | With Oxone; sodium chloride In tert-butyl methyl ether; water at 20℃; for 1h; Green chemistry; regioselective reaction; | |
With water; chlorine; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With Phenylselenyl bromide; water; potassium carbonate In tetrahydrofuran at 20℃; for 6h; regioselective reaction; | |
87% | With Oxone; tetra(n-butyl)ammonium hydrogensulfate; Sodium 2-iodo-5-methylbenzenesulfonate at 40℃; for 12h; | |
80% | With tert.-butylhydroperoxide; 3 A molecular sieve In dichloromethane at 22℃; for 22h; |
80% | With N1-benzylcinchonidinium chloride; 3-(4-nitrophenyl)-2-p-tolylsulfonyloxaziridine; sodium hydroxide In toluene at 20℃; for 2h; chemoselective reaction; | |
80% | With Oxone; sodium hydrogencarbonate In water; acetone at 20℃; for 1h; | |
With chromium(VI) oxide; acetic acid | ||
With benzene | ||
With peracetic acid | ||
bei mehrjaehrigem Aufbewahren im Dunkeln unter Luftzutritt; | ||
With tert.-butylhydroperoxide; zirconium acetyacetonate In dichloromethane Yield given; | ||
Multi-step reaction with 2 steps 1: diethyl ether; mixture of gaseous nitrogen oxides 2: glacial acetic acid; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; water; sodium hydrogensulfite at 200℃; | ||
With ammonium sulfite; ammonia; water at 150℃; man erwaermt das Reaktionsprodukt mit verd. Natronlauge auf dem Wasserbad; | ||
With ammonia; calcium chloride at 270℃; |
With ammonium sulfite; ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-Bromosuccinimide; potassium acetate In water at 20℃; for 0.333333h; Green chemistry; | |
With bromine; sodium acetate; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bromine; acetic acid at 10 - 20℃; for 0.25h; | 5.12. 6-Bromo-1-methyl-2-naphthol (11c) A solution of bromine (16.1 g, 101 mL) in AcOH (30 mL) was added dropwise to a cooled (10 °C) solution of 12 (16.0 g, 101 mmol) in AcOH (50 mL); the temperature of the solution was maintained at 10-20 °C. After stirring for 15 min at 15-20 °C, the mixture was poured into water. The precipitate was filtered, washed with water, and dried in vacuo to give 11c (23.7 g, 99%) as a reddish powder. 1H NMR (CDCl3) δ: 2.49 (3H, s), 4.94 (1H, s), 7.05 (1H, d, J = 8.8 Hz), 7.50 (1H, d, J = 8.8 Hz), 7.52 (1H, dd, J = 2.2, 9.0 Hz), 7.76 (1H, d J = 9.0 Hz), 7.89 (1H, d, J = 2.2 Hz). IR (KBr): 3245, 1591, 1497, 1356, 1341, 1198, 1080, 893, 878, 810 cm-1. Anal. Calcd for C11H9OBr: C, 55.72; H, 3.83. Found: C, 55.70; H, 3.81. |
With bromine; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper oxide-chromium oxide at 200℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ethoxyethoxyethanol; hydrazine hydrate; potassium hydroxide at 220℃; Sonication; | |
89% | With hydrazine hydrate; potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 170 - 190℃; for 1.83333h; | 5.11. 1-Methyl-2-naphthol (12) A mixture of 2-hydroxy-1-naphthaldehyde (20.0 g, 116 mmol), hydrazine monohydrate (16.9 mL, 348 mmol) and KOH (20 g) in triethyleneglycol (150 mL) was slowly heated to 170 °C in a round-bottomed flask equipped with Dean-Stark apparatus. The mixture was then heated at 170 °C for 90 min and at 190 °C for a further 20 min. After cooling to rt, the mixture was poured into water and acidified with concentrated HCl. The precipitate was filtered, washed with water, and dried in vacuo to give 12 (16.3 g, 89%) as a pale yellow powder. The analytical sample was obtained by recrystallization from i-Pr2O-hexane (colorless needles). 1H NMR (CDCl3) δ: 2.52 (3H, s), 4.91 (1H, br s), 7.04 (1H, d, J = 8.8 Hz), 7.29-7.37 (1H, m), 7.44-7.52 (1H, m), 7.60 (1H, d, J = 8.8 Hz), 7.75 (1H, d, J = 8.0 Hz), 7.90 (1H, d, J = 8.4 Hz). IR (KBr): 3295, 1514, 1354, 1227, 1213, 806, 742 cm-1. Anal. Calcd for C11H10O: C, 83.51; H, 6.37. Found: C, 83.55; H, 6.46. |
With hydrogenchloride; amalgamated zinc; acetic acid |
With acetic acid | ||
With potassium hydroxide; hydrazine hydrate | ||
With acetic acid; platinum at 20℃; Hydrogenation; | ||
With acetic acid; zinc | ||
(i) ClCO2Et, Et3N, (ii) NaBH4; Multistep reaction; | ||
With sodium bis(2-methoxyethoxy)aluminium dihydride In xylene; benzene | ||
Multi-step reaction with 2 steps 1: aq. NaOAc / methanol 2: H2 / Pd-BaSO4 | ||
Multi-step reaction with 2 steps
1: Na |
||
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 120h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 1-methyl-2-naphthol With n-butyllithium In toluene at 0 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: benzyl bromide In toluene at 90℃; for 20h; Inert atmosphere; regioselective reaction; | 1-benzyl-1-methylnaphthalen-2(1H)-one (4c) To 1c (79 mg, 0.5 mmol) solution in CPME (116 mL) at 0 °C n-BuLi 2.7 M in toluene (0.17 mL, 0.45 mmol) was added dropwise. Then toluene was added (0.3 mL). The reaction mixture was stirred for 15 min and then at room temperature for 20 min 2a (171 mL,1 mmol) was added dropwise and reaction mixture was stirred at 90 °C for 20 h. Reaction was diluted with water and extracted with EtOAc (3x7 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography PE/EtOAc(1-20 %). To give 1-benzyl-1-methylnaphthalen-2(1H)-one 4c as a yellow oil (111 mg, 90 %). PE/EtOAc 10:1, Rf = 0.35. IR (neat): 3028.60, 1656.05, 1452.90, 835.56, 759.04, 700.87 cm-1 1H NMR(400 MHz, CDCl3) δ 7.48-7.38 (m, 2H), 7.29-7.22 (m, 1H), 7.20-7.10(m, 2H), 7.07-6.94 (m, 3H), 6.65-6.56 (m, 2H), 5.98 (d, J 9.8 Hz,1H), 3.37 (d, J 13.0 Hz, 1H), 3.05 (d, J 13.0 Hz, 1H),1.59 (s, 3H). 13CNMR (101 MHz, CDCl3) δ 204.00, 145.41, 145.03, 136.60, 130.06, 129.77, 129.66, 129.42, 127.61, 127.30, 126.94, 126.40, 125.48, 52.81, 49.75, 26.37. HRMS (ESI) m/z calculated for C18H16ONa [M+Na]+ 271.1093, found 271.1091. |
(i) nBuLi, hexane, benzene, (ii) /BRN= 385801/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate In acetone; toluene at 20℃; Inert atmosphere; | |
(i) aq. NaOH, (ii) /BRN= 605309/; Multistep reaction; | ||
With potassium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyrrolidine; tris(2,4-pentanedionato)ruthenium(III); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 20h; Sealed tube; | |
at 300℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: 2-hydroxy-1-naphthalenecarboxylic acid With chloroacetic acid ethyl ester; triethylamine Stage #2: With sodium tetrahydroborate | |
56% | Stage #1: 2-hydroxy-1-naphthalenecarboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 3h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; for 4h; | |
(i) ClCO2Et, Et3N, THF, (ii) aq. NaBH4; Multistep reaction; |
With sodium bis(2-methoxyethoxy)aluminium dihydride In xylene; benzene | ||
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 2 h / 0 °C 2: aq. NaBH4 / tetrahydrofuran / 0 °C | ||
Multi-step reaction with 2 steps
1: Na |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With cerium(IV) sulphate; oxygen In <i>tert</i>-butyl alcohol at 80℃; | |
With palladium on activated charcoal In 1,3,5-trimethyl-benzene for 3h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,4-dioxane; copper oxide-chromium oxide at 165℃; Hydrogenolyse; | ||
With methanol; sodium methylate at 220℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: 2-methoxy-1-naphthaldehyde With potassium hydroxide; hydrazine hydrate In diethylene glycol for 1.5h; Heating; Stage #2: With pyridine hydrochloride for 0.5h; Heating; Further stages.; | |
Multi-step reaction with 2 steps 1: N2H4+H2O; KOH; diethylene glycol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium hydride In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Raney nickel; ethanol / 110 °C / 73550.8 Torr / Hydrogenation 2: aqueous NaOH / 80 - 100 °C 3: CrO3; water containing acetic acid / <20 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridine In dichloromethane at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; copper(l) iodide; (E)-1-(2-pyridinyl)methylene-2-phenylhydrazine; In 1,4-dioxane; at 95 - 105℃;Inert atmosphere; | General procedure: To a solution of 8aa or 8ab (30 mmol) and substituted naphthols(20 mmol) in dioxane (20 mL) was added CuI (0.38 g, 2 mmol), (E)-1-(2-pyridinyl)methylene-2-phenyl hydrazine (0.39 g, 2 mmol) and K3PO4 (8.49 g, 40 mmol) under N2 atmosphere. The mixture was stirred and heated to 95-105 C for 36-48 h. Then the mixture was filtered, and the filter cake was washed with n-hexane(4 × 10 mL). The combined filtrate and wash liquor was evaporated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (60-90 C petroleum ether as eluent) to obtain 9a-t as pure white solids in the yield of 11-52%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride; water In methanol at 50℃; for 1h; | |
86% | With hydrogenchloride; methanol at 50℃; for 1h; | 1-Methyl-2-naphthol N2 (2.5 mmol, 1 eq.) was dissolved in MeOH (8 mL) and warmed to 50 °C. Then conc. HCl (37 %, 3 drops) was added and the mixture was stirred for 1 h. After cooling to room temperature 8 mL of demin. water were added and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure, to give the crude product, which was purified by column chromatography (petroleum ether/EtOAc 20:1) to afford 1-Methyl-2-naphthol as a white solid (0.34 g, 2.2 mmol, 86 %). |
With hydrogenchloride; water In methanol for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 8h; Inert atmosphere; | ||
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A borosilicate flask was equipped with a magnetic stir bar, and neat or solid arene (0.2-0.8mmol) was added. Addition of hexafluoroisopropanol or trifluoroethanol (2-5 ml) to providea 0.2M solution was followed by the addition of solid phthaloyl peroxide (1, 1.3 equiv.) in portions over 90 s. The reaction flask was placed in a heated oil bath (23-50 C). After 3-24 h, the flask was removed from the oil bath and cooled to ambient temperature (23 C). The reaction was then concentrated, and under positive N2 pressure (to avoid potential air oxidation of the phenolic product) MeOH (3 ml) and saturated aqueous NaHCO3 solution (0.2 ml) were added and the solution was stirred. After 12 h, the reaction was quenched with phosphate buffer (5 ml, pH 7.0) and extracted with EtOAc (10 ml x 33), and the combined organic layers were washed with brine (5 ml), dried over Na2SO4 and concentrated. The crude material was purified by silica-gel column chromatography to afford the desired phenolic product. For full experimental details and characterization of new compounds, see Supplementary Information. | ||
General procedure: General procedure for the hydroxylation of arenes: A borosilicate flask was equipped with a magnetic stir bar and neat or solid arene (0.2-0.8 mmol) was added. Addition of HFIP or TFE (2-5 mL) to provide a 0.2 M solution was followed by the addition of solid phthaloyl peroxide (1, 1.3 equiv.) in portions over 90 seconds. The reaction flask was placed in a heated oil bath (23-50 C). After 3-24 hours, the reaction was removed from the oil bath and cooled to ambient temperature (23 C). The reaction was then concentrated and under positive N2 pressure (to avoid potential air oxidation of the phenolic product) MeOH (3 mL) and saturated aqueous NaHC03 solution (0.2 mL) were added and the solution was stirred. After 12 hours, the reaction was quenched with pH 7.0 phosphate buffer (5 mL) and extracted with EtOAc (10 mL x 3) and the combined organic layers were washed with brine (5 mL), dried over Na2S04, and concentrated. The crude material was purified by silica gel column chromatography to afford the desired phenolic product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 2-hydroxy-1-methylnaphthalene With (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In o-dimethylbenzene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: diethylazodicarboxylate In o-dimethylbenzene at 20℃; for 4h; Inert atmosphere; enantioselective reaction; | |
93% | With BINOL-derived chiral phosphoric acid hyper-crosslinked porous polymer In o-dimethylbenzene at 20℃; for 4h; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 1-methyl-2-naphthol With triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: Allyl chloroformate In dichloromethane at 20℃; for 0.1h; Inert atmosphere; | General procedure for the synthesis of alloc protected 2-naphthol derivatives (GP III): [4] General procedure: The methylated naphthol derivative (1 eq.) was weighed into a flame dried round bottom flask under nitrogen atmosphere and dissolved in dry CH2Cl2 (c = 0.1 mol/L). Then Triethylamine (1.1 eq.) was slowly added at room temperature and stirred for 5 minutes. Afterwards Allyl chloroformate (2.5 eq.) was added over 1 minute. After stirring for additional 5 minutes the reaction was quenched with 25 % EtOAc/petroleum ether and filtered over a silica plug. The received organic solution was concentrated under reduced pressure to give the desired Alloc protected naphthol derivative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium 2-methylbutan-2-olate; tetrabutylammonium tricarbonylnitrosylferrate; 1,3-Di-tert-butyl-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate In ethyl acetate; toluene; acetonitrile at 60℃; for 18h; Schlenk technique; Inert atmosphere; | Dearomatization of 1,3-Disubstituted Naphthols Catalyzed by the Iron Complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]); General Procedure II (GP II) General procedure: A 10 mL Schlenk tube was charged with L2 (2.1 mg, 0.006 mmol, 0.03 equiv) and MeCN (1 mL). Afterwards KOt-Am solution (1.7 M in toluene, 6 μL, 0.01 mmol, 0.05 equiv) was added and the reaction mixturewas stirred for 20 min at r.t. Then Bu4N[Fe(CO)3NO] (1.1 mg, 0.002mmol, 0.01 equiv) was added and the mixture was heated for 1 h at 80 °C to coordinate the ligand. At r.t. the carbonate (0.2 mmol, 1 equiv) was added to the mixture, followed by the naphthol (0.2 mmol, 1 equiv) and the co-solvent EtOAc (0.05 mmol). The reaction mixture was stirred for 18 h at 60 °C. After filtration through a silica plug (Et2O), the crude product was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 12% 2: 63% | With potassium 2-methylbutan-2-olate; tetrabutylammonium tricarbonylnitrosylferrate; 1,3-Di-tert-butyl-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate In ethyl acetate; toluene; acetonitrile at 60℃; for 18h; Schlenk technique; Inert atmosphere; | Dearomatization of 1,3-Disubstituted Naphthols Catalyzed by the Iron Complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]); General Procedure II (GP II) General procedure: A 10 mL Schlenk tube was charged with L2 (2.1 mg, 0.006 mmol, 0.03 equiv) and MeCN (1 mL). Afterwards KOt-Am solution (1.7 M in toluene, 6 μL, 0.01 mmol, 0.05 equiv) was added and the reaction mixturewas stirred for 20 min at r.t. Then Bu4N[Fe(CO)3NO] (1.1 mg, 0.002mmol, 0.01 equiv) was added and the mixture was heated for 1 h at 80 °C to coordinate the ligand. At r.t. the carbonate (0.2 mmol, 1 equiv) was added to the mixture, followed by the naphthol (0.2 mmol, 1 equiv) and the co-solvent EtOAc (0.05 mmol). The reaction mixture was stirred for 18 h at 60 °C. After filtration through a silica plug (Et2O), the crude product was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With potassium 2-methylbutan-2-olate; tetrabutylammonium tricarbonylnitrosylferrate; 1,3-Di-tert-butyl-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate In ethyl acetate; toluene; acetonitrile at 60℃; for 18h; Schlenk technique; Inert atmosphere; | Dearomatization of 1,3-Disubstituted Naphthols Catalyzed by the Iron Complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]); General Procedure II (GP II) General procedure: A 10 mL Schlenk tube was charged with L2 (2.1 mg, 0.006 mmol, 0.03 equiv) and MeCN (1 mL). Afterwards KOt-Am solution (1.7 M in toluene, 6 μL, 0.01 mmol, 0.05 equiv) was added and the reaction mixturewas stirred for 20 min at r.t. Then Bu4N[Fe(CO)3NO] (1.1 mg, 0.002mmol, 0.01 equiv) was added and the mixture was heated for 1 h at 80 °C to coordinate the ligand. At r.t. the carbonate (0.2 mmol, 1 equiv) was added to the mixture, followed by the naphthol (0.2 mmol, 1 equiv) and the co-solvent EtOAc (0.05 mmol). The reaction mixture was stirred for 18 h at 60 °C. After filtration through a silica plug (Et2O), the crude product was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With potassium 2-methylbutan-2-olate; tetrabutylammonium tricarbonylnitrosylferrate; 1,3-Di-tert-butyl-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate In ethyl acetate; toluene; acetonitrile at 60℃; for 18h; Schlenk technique; Inert atmosphere; | Dearomatization of 1,3-Disubstituted Naphthols Catalyzed by the Iron Complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]); General Procedure II (GP II) General procedure: A 10 mL Schlenk tube was charged with L2 (2.1 mg, 0.006 mmol, 0.03 equiv) and MeCN (1 mL). Afterwards KOt-Am solution (1.7 M in toluene, 6 μL, 0.01 mmol, 0.05 equiv) was added and the reaction mixturewas stirred for 20 min at r.t. Then Bu4N[Fe(CO)3NO] (1.1 mg, 0.002mmol, 0.01 equiv) was added and the mixture was heated for 1 h at 80 °C to coordinate the ligand. At r.t. the carbonate (0.2 mmol, 1 equiv) was added to the mixture, followed by the naphthol (0.2 mmol, 1 equiv) and the co-solvent EtOAc (0.05 mmol). The reaction mixture was stirred for 18 h at 60 °C. After filtration through a silica plug (Et2O), the crude product was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole); scandium tris(trifluoromethanesulfonate) In dichloromethane at 40℃; for 36h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: 1-bromo-2-(methoxymethoxy)naphthalene With n-butyllithium In tetrahydrofuran at -70℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In methanol; water for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate In toluene at 80℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With methanol; tris(2,4-pentanedionato)ruthenium(III); benzyl-methyl-amine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at -75℃; for 12h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at -75℃; for 15h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at -75℃; for 15h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C39H60N4O4; scandium trifluoromethanesulfonimide; 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine In dichloromethane at 0℃; for 3h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium azide; phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With tetra-(n-butyl)ammonium iodide In nonane; 1,2-dichloro-ethane at 50℃; for 12h; | Typical Procedure for the Peroxidative Dearomatization of 6 to 7 General procedure: To a solution of 6a (0.250 g,1.00 mmol) and tetrabutylammonium iodide (0.0369 g, 0.100 mmol, 10 mol%) in 1,2-dichloroethane (100 mL) was added tert-butyl hydroperoxide (1.81 mL, 10.0 mmol, 5.5 M in nonane) at room temperature. The reaction was monitored by TLC analysis. After 36 h, the resulting mixture was cooled to 0 °C and quenched by saturated aqueous NaHSO3 (20 mL). The aqueous layers were separated and extracted with CHCl3 (twice). The combined organic layers were washed with brine anddried over anhydrous MgSO4, and then the solvents were removed in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: Hexane-EtOAc = 10:1 to 4:1) to give desired 7a |
75% | With phenyltrimethylammonium tribromide; potassium carbonate In tetrahydrofuran; water at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With water; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With water; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With water; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With water; caesium carbonate In N,N-dimethyl-formamide at -78 - 20℃; for 2h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 % ee | With C27H28Br2N4S; ethylene glycol In dichloromethane at 25℃; for 75h; Overall yield = 74 %; Overall yield = 42 mg; enantioselective reaction; | |
87 % ee | With C26H26Br2N4S In dichloromethane; ethylene glycol at 20℃; for 75h; Inert atmosphere; Schlenk technique; Overall yield = 74 %; enantioselective reaction; | 2; 8; 9 Preparation of (S)-1-((2-fluorophenyl)thio)-1-methyl-2(1H)-naphthalenone 1-methyl-2-naphthol (0.2 mmol) at room temperature under the protection of an inert gas (nitrogen or argon)2,5-Dibromophenylthiourea (0.02 mmol) was added to the Schlenk bottle.Replace the inert gas three times, then add ethylene glycol (0.6mmol)And 2mL of dichloromethane (calcium hydride distillation to remove water), stir well,Further, N-(2-fluorophenyl)thiosuccinimide (0.24 mmol) was added to the above reaction system, and the mixture was reacted at room temperature for 75 hours.After TLC monitoring, after the reaction was completed, the solvent was removed under reduced pressure and purified by column chromatography ( petroleum ether: ethyl acetate = 10:1).(S)-1-((2-Fluorophenyl)thio)-1-methyl-2(1H)-naphthalenone (yellow liquid, yield: 74%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); potassium hydrogencarbonate; benzoic acid; tricyclohexylphosphine In toluene at 100℃; for 12h; Inert atmosphere; Sealed tube; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 % ee | With C26H26Br2N4S In dichloromethane; ethylene glycol at 20℃; for 75h; Inert atmosphere; Schlenk technique; Overall yield = 68 %; enantioselective reaction; | 1; 6; 7 Preparation of (S)-1-methyl-1-phenylthio-2-(1H)-naphthalenone Under the protection of an inert gas (nitrogen or argon),1-methyl-2-naphthol (0.2 mmol) and 2,5-dibromophenylthiourea (0.02 mmol) were added to the Schlenk bottle at room temperature.Replace the inert gas three times,Add ethylene glycol (0.6mmol)And 2mL of dichloromethane (calcium hydride distillation to remove water),Stir well, and then add N-phenylthiosuccinimide (0.24 mmol) to the above reaction system.Reaction at room temperature for 75 h,After TLC monitoring, after the reaction was completed, the solvent was removed under reduced pressure and purified by column chromatography ( petroleum ether: ethyl acetate = 10:1).(S)-1-Methyl-1-phenylthio-2-(1H)-naphthalenone (yellow liquid, yield: 68%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 90℃; for 2.25h; | (0081) This dimer was produced according to the following reaction: (0082) Precursor molecule 2-naphthol (0.208 mmol) and acetic acid for a solvent and catalyst (20 mL) were charged to a 25 mL flask and the reaction temperature was set to 90 C. Once all 2-naphthol had dissolved and the reaction temperature had reached 90 C. paraformaldehyde (the first bridging molecule) (0.180 mmol) was added. After stirring for 1 hour the reaction mixture was allowed to cool to room temperature and a second aliquot of paraformaldehyde (0.030 mmol) was added. The reaction temperature was brought back to 90 C. then the reaction mixture was stirred for an additional 75 minutes. The reaction was then cooled to room temperature and acetic acid was evaporated under a gentle stream of nitrogen. The resultant products including 1,1?-methylene-bis(naphthalen-2-ol) were transferred to a sample vial. GC-MS results of the reaction products were compared to those observed for a standard of the target compound 1,1?-methylene-bis(naphthalen-2-ol). Peaks at two different retention times (RT) were observed in the standard chromatogram for 1,1?-methylene-bis(naphthalen-2-ol), shown in FIG. 2, as well as in the chromatogram from the reaction products. The two peaks represent the degradation products of 1-1?methylene-bis(napthaen-2-ol), those products being 2-naphthol and 1-methyl-2-naphthol. The degree of difference in observed TC and TM for the phenol standard and BPA standard is representative of the difference in TC and TM observed for 2-naphthol and the reaction products from R4. TM observed for the reaction products is 204.20 C. which is 50 C. higher than the TM observed for BPA, however as trans esterification and polymerization still occurs at temperatures above 204 C., 1,1?-methylene-bis(naphthalen-2-ol) has the potential to be utilized as a polycarbonate precursor. Several weight percent loss temperatures were observed for the reaction products during TGA characterization, all of which were above that observed for 2-naphthol. The latter indicates that the products obtained from this reaction either degrade or volatilize at a higher temperature than the starting material which is also an indication of successful dimerization and an increase in thermal stability from starting material to products. (0083) 1,1?-methylene-bis(naphthalen-2-ol) dimer was |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; | |
79% | With 9-(2-mesityl)-10-methylacridinium perchlorate In 1,2-dichloro-ethane at 20℃; for 58h; Schlenk technique; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tetrakis(triphenylphosphine) palladium(0); tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,6-dimethoxy-p-quinone In acetonitrile at 40℃; for 48h; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With (trifluoroacetato)(triphenylphosphine)gold(I) In chlorobenzene at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With iron(II) chloride In 1,2-dichloro-ethane at 80℃; for 11h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 82% 2: 13% | With sodium hypochlorite pentahydrate In water; ethyl acetate at 20℃; for 0.0833333h; Green chemistry; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With [2,2]bipyridinyl; manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 7h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; (-)-sparteine In dichloromethane at 20℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With copper(l) iodide; (-)-sparteine In dichloromethane at 20℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With copper(l) iodide; (-)-sparteine In dichloromethane at 20℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(l) iodide; (-)-sparteine In dichloromethane at 20℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(l) iodide; (-)-sparteine In dichloromethane at 20℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 41% 2: 40% | With tetra-(n-butyl)ammonium iodide In nonane; 1,2-dichloro-ethane at 20℃; for 12h; | Typical Procedure for the Peroxidative Dearomatization of 6 to 7 General procedure: To a solution of 6a (0.250 g,1.00 mmol) and tetrabutylammonium iodide (0.0369 g, 0.100 mmol, 10 mol%) in 1,2-dichloroethane (100 mL) was added tert-butyl hydroperoxide (1.81 mL, 10.0 mmol, 5.5 M in nonane) at room temperature. The reaction was monitored by TLC analysis. After 36 h, the resulting mixture was cooled to 0 °C and quenched by saturated aqueous NaHSO3 (20 mL). The aqueous layers were separated and extracted with CHCl3 (twice). The combined organic layers were washed with brine anddried over anhydrous MgSO4, and then the solvents were removed in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: Hexane-EtOAc = 10:1 to 4:1) to give desired 7a |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 35% 2: 7% | With iodine In water; acetonitrile at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With bis(1,5-cyclooctadiene)nickel (0); bis[2-(diphenylphosphino)phenyl] ether In toluene at 25℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81 % ee | With C69H48O6; sodium carbonate; Selectfluor In dichloromethane at 0℃; for 18h; Overall yield = 92 percent; Overall yield = 16.2 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: 1-methyl-2-naphthol With n-butyllithium In toluene at 0℃; Inert atmosphere; Stage #2: prenyl bromide In toluene at 20℃; for 20h; Inert atmosphere; regioselective reaction; | General method A General procedure: To the corresponding naphthol (1a-1c) (0.5 mmol) solution in toluene (0.6 mL) at 0 °C n-BuLi 2.7M in toluene (0.22 mL, 0.6 mmol) was added dropwise. The reaction mixture was stirred for 15 min and then at room temperature until precipitation occurred or 20 min. As an additive CPME (116 mL, 1 mmol) was added dropwise and stirred for 5 min. Alkylating agent 2a-2g (1.2 equiv) was added dropwise/portion wise and the reaction mixture was stirred at 80 °C for 20 h. The reaction mixture was diluted with water and extracted with EtOAc (3x7 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (PE/EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% ee | With bis(η3-allyl-μ-chloropalladium(II)); N-allyl-N-methyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; caesium carbonate In toluene at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; enantioselective reaction; | |
82 % ee | With bis(η3-allyl-μ-chloropalladium(II)); N-allyl-N-methyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; caesium carbonate In toluene at 0℃; Sealed tube; Overall yield = 79 percent; | 6 Example 7 Under the protection of nitrogen, add 1-methyl-β-naphthol (0.1mmol), N-2-iodophenyl-N-Ts-dienamine (0.11mmol), [Pd (C3H5)Cl]2 (1 mol%), L5 (1 mol%) and Cs2CO3 (0.15 mmol), sealed with a rubber stopper. The syringe injects 1.0 mL of dry toluene into the reaction tube. Place the reaction tube at 0°C and stir overnight. The reaction solution quickly passed through a short silica gel column and eluted with dichloromethane/methanol=15/1. After the solution was concentrated in vacuo, a crude product was obtained. Following silica gel column chromatography purification, a yellow solid 3fa was obtained with a yield of 79% and 82% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With toluene-4-sulfonic acid In toluene at 20℃; for 6h; Schlenk technique; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyaninato)iron(II); boron trifluoride diethyl ether complex In dichloromethane at 20℃; for 0.5h; |
Tags: 1076-26-2 synthesis path| 1076-26-2 SDS| 1076-26-2 COA| 1076-26-2 purity| 1076-26-2 application| 1076-26-2 NMR| 1076-26-2 COA| 1076-26-2 structure
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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