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CAS No. : | 774-55-0 | MDL No. : | MFCD00019710 |
Formula : | C12H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEPUKHYQNXSSKV-UHFFFAOYSA-N |
M.W : | 174.24 | Pubchem ID : | 69885 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.07 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.28 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 2.94 |
Log Po/w (WLOGP) : | 2.77 |
Log Po/w (MLOGP) : | 2.58 |
Log Po/w (SILICOS-IT) : | 3.68 |
Consensus Log Po/w : | 2.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.05 |
Solubility : | 0.156 mg/ml ; 0.000895 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.96 |
Solubility : | 0.191 mg/ml ; 0.0011 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.84 |
Solubility : | 0.0253 mg/ml ; 0.000145 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
80% | With sulfur for 24h; Heating; | |
61% | With 4-methyl-morpholine; sulfur In N,N-dimethyl-formamide for 2h; microwave irradiation; | |
With sulfur |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide In ethanol at 20℃; | |
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogen bromide; dihydrogen peroxide In 1,4-dioxane for 0.333333h; Heating; | |
With carbon disulfide; bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hypobromide In water 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp.; | |
With 1,4-dioxane; sodium hydroxide; iodine; potassium iodide | ||
With sodium hypochlorite |
With water; calcium chloride | ||
With 1,4-dioxane; sodium hypochlorite | ||
With sodium hydroxide; bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; amalgamated zinc | ||
With potassium hydroxide; hydrazine hydrate; diethylene glycol | ||
With hydrogenchloride; methanol; amalgamated zinc Reagens 4: Benzol; |
With potassium hydroxide; hydrazine hydrate In diethylene glycol at 150 - 190℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With sodium tetrahydroborate In ethanol Stage #2: With hydrogenchloride In ethanol; water | |
With aluminum isopropoxide; isopropyl alcohol | ||
With copper oxide-chromium oxide at 130℃; Hydrogenation; |
With sodium tetrahydroborate | ||
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 20 - 25 °C / Inert atmosphere 1.2: 20 - 25 °C / Inert atmosphere 2.1: crithmene; 2,2,6,6-tetramethyl-piperidine; tris(pentafluorophenyl)borate / toluene / 16 h / 130 °C / Inert atmosphere; Glovebox 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 80 °C | ||
With methanol; sodium tetrahydroborate at 0 - 20℃; Inert atmosphere; Schlenk technique; | ||
Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With sodium tetrahydroborate; ethanol at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium azide; sulfuric acid In acetic acid at 65 - 105℃; | |
With sodium azide; sulfuric acid; benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With Oxone; ammonium bromide In methanol at 20℃; for 3h; Inert atmosphere; Reflux; | |
89% | With bromine In methanol at 0 - 20℃; for 18.75h; | 4.A Example 4 - Preparation of 2-chloro-6-(5',6',78Metrahvdronaphthalen-2'- vnimidazoβ.l-blthiazole f Compound 25); A. Preparation of 2-bromo-l-(5',6',7',8'-tetrahydronaphthalen-2'- yl)ethanone; Bromine (0.63 mL, 12.3 mmol) was added to a stirred solution of l-(5',6',7',8'- tetrahydronaphthalen-2'-yl)ethanone (2.13 g, 12.3 mmol) in methanol (15 mL) at O0C and the resultant solution allowed to stir for 2.75 hours before the reaction mixture was diluted with water and allowed to warm to room temperature over 16 hours. After this time, the reaction mixture was extracted with ethyl acetate:40-60 petrol (v:v 3:1, x3) and the combined organic layers washed with 10% aqueous potassium carbonate solution, dried over MgSO4 and concentrated in vacuo to furnish the crude product (2.755g, 89%).1H NMR (DMSO) 7.68-7.71 (2H, m), 7.22 (IH, d, J 8.6Hz), 4.86 (2H, s), 2.78 (4H, br s), 1.73-1.77 (4H, m). |
With carbon disulfide; bromine |
With aluminium trichloride; bromine In diethyl ether | ||
With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 15h; | 2-Bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone 25 g (143 mmol) of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone are dissolved in 750 ml of THF, 64.7 g (172 mmol) of phenyltrimethylammonium tribromide are added, and the mixture is stirred at room temperature for 15 h. The precipitate formed is filtered, and the filtrate is evaporated to dryness. The residue is taken up in ethyl acetate, washed 2* with saturated sodium hydrogencarbonate solution and 1* with saturated sodium chloride solution, the organic phase is dried over sodium sulfate and evaporated to dryness. Yield: 62 g, white solid; HPLC: Rt.=3.06 min. | |
With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 15h; | I Preparation of 2-bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone 25 g (143 mmol) of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone were dissolved in 750 ml of THF, 64.7 g (172 mmol) of phenyltrimethylammonium tribromide were added, and the mixture was stirred at room temperature for 15 h. The resultant precipitate was filtered, and the filtrate was evaporated to dryness. The residue was taken up in ethyl acetate, washed with 2*sat. sodium hydrogencarbonate solution and 1*sat. sodium chloride solution, the organic phase was dried over sodium sulfate and evaporated to dryness. Yield: 62 g, white solid. HPLC: Rt.=3.06 min. | |
With bromine | ||
With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; | Intermediate 133A 2-bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one Trimethylphenylammonium tribromide (2.16 g, 5.74 mmol) was added in portions to a solution of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one (1.00 g, 5.74 mmol) in THF (10 ml) at RT. The mixture was subsequently stirred at RT. After completion of the reaction, the mixture was filtered, and the filtrate was concentrated to afford the crude product which was used in the next step without further purification. Yield: 1.70 g (78% of theory, 67% purity). LC/MS [Method 7]: Rt = 1.10 min; MS (ESIpos): m/z = 255 [M+H]+. | |
With copper(ll) bromide In ethyl acetate Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum isopropoxide Behandlung des heissen Reaktionsgemisches mit Mineralsaeure; | ||
Multi-step reaction with 2 steps 1: copper oxide-chromium oxide / 130 °C / 73550.8 Torr / Hydrogenation 2: 290 - 310 °C / Leiten ueber Aluminiumoxyd |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With aluminium trichloride In dichloromethane | |
85% | With aluminium trichloride In dichloromethane for 15h; Ambient temperature; | |
85% | With trifluoroacetic acid at 100℃; for 56h; Inert atmosphere; | Conditions B (used in Table 3, bottom) General procedure: An oven-dried vial was charged with isobutylbenzene 1p (0.75 mmol, 1.0 equiv), acetic anhydride 2a (1.125 mmol, 1.5 equiv) and TFA (2 mL). The reaction mixture was stirred at 100 oC for 56 h and monitored by TLC or GC-MS. Upon completion, the solvent was removed under reduced pressure and the residue was subjected to silica gel flash column chromatography (hexanes : AcOEt) to give ketone product 3x. |
With aluminium trichloride; nitrobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With aluminium trichloride In nitrobenzene at 0 - 25℃; for 2h; | |
90% | With aluminium trichloride | |
43% | With aluminium trichloride In various solvent(s) at 20℃; for 3h; |
With carbon disulfide; aluminium trichloride | ||
With aluminium trichloride; benzene | ||
With tetrachloromethane; aluminium trichloride | ||
With aluminium trichloride | ||
With aluminium trichloride In 1,2-dichloro-ethane | ||
With aluminium trichloride | ||
With aluminum (III) chloride In dichloromethane at 0℃; | ||
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 6h; | ||
Stage #1: tetralin; acetyl chloride Stage #2: With aluminum (III) chloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 3-chloro-benzenecarboperoxoic acid In chloroform for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With jones reagent at 0℃; for 0.0166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With triethylamine; zinc(II) chloride In acetonitrile for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With silica gel column chromatography; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide In ethanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With ammonium acetate In butan-1-ol for 10h; Heating; | |
With ammonium acetate In butan-1-ol | ||
With ammonium acetate In butan-1-ol for 6h; Reflux; | General procedure: A mixture of 6-acetyl-1,2,3,4-tetrahydronaphthalene(6.0 g, 0.034 mol), the appropriate aldehydenamely: 3,4-dimethoxybenzaldehyde and/or 4-fluorobenzaldehyde(0.034 mol), ethyl cyanoacetate (3.8mL, 0.034 mol) and ammonium acetate (21.0 g,0.272 mol) in n-butanol (50 mL) was refluxed for 6h. The formed precipitate was filtered, washed withether, dried and recrystallized from acetic acid togive the title compounds 1a,b, respectively. |
With ammonium acetate In butan-1-ol Reflux; | ||
With ammonium acetate Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; zinc In benzene for 2h; Heating; | ||
With iodine; zinc In benzene Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: zinc; iodine / benzene / 2 h / Heating 2.1: 10 g / p-TSA / benzene / 5 h / Heating 3.1: 72 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 4.1: oxygen / methylene blue / acetonitrile / 5 h / -10 - 0 °C / Irradiation 4.2: 46 percent / aq. HCl / acetonitrile / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating | ||
Multi-step reaction with 2 steps 1: dioxane; aqueous sodium hypochlorite solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene 6: 81 percent / KOH / methanol; H2O / 48 h / Heating 7: polyphosphoric acid / 2 h / 120 °C | ||
Multi-step reaction with 8 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene 6: 81 percent / KOH / methanol; H2O / 48 h / Heating 7: SOCl2 / Heating 8: SnCl4 / benzene / 4 h / Heating | ||
Multi-step reaction with 11 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / pyridiniumchlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 86.5 percent / piperidine / pyridine / 24 h / 80 °C 6: 95 percent / H2 / Pd/C (10percent) / dioxane / 750.06 - 1500.1 Torr 7: polyphosphoric acid / 5 h / 80 °C 8: 97 percent / 50percent NaH / benzene / 48 h / Heating 10: 90 percent / KOH / methanol; H2O / 48 h / Heating 11: polyphosphoric acid / 15 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene 6: 88 percent / KOH / methanol; H2O / 48 h / Heating 7: SOCl2 / Heating 8: SnCl4 / benzene / 4 h / Heating | ||
Multi-step reaction with 6 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene 6: polyphosphoric acid / 15 h / 90 - 95 °C | ||
Multi-step reaction with 7 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene 6: SOCl2 / Heating 7: SnCl4 / benzene / 3 h / Heating |
Multi-step reaction with 12 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / pyridiniumchlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 86.5 percent / piperidine / pyridine / 24 h / 80 °C 6: 95 percent / H2 / Pd/C (10percent) / dioxane / 750.06 - 1500.1 Torr 7: polyphosphoric acid / 5 h / 80 °C 8: 97 percent / 50percent NaH / benzene / 48 h / Heating 10: 88 percent / KOH / methanol; H2O / 48 h / Heating 11: SOCl2 / Heating 12: SnCl4 / benzene / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene | ||
Multi-step reaction with 6 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene | ||
Multi-step reaction with 6 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / SOCl2 / benzene |
Multi-step reaction with 9 steps 1: 80 percent / NaOBr / H2O / 1.) 3 h, 0 deg C; 2.) 2.5 h, room temp. 2: 87 percent / conc. H2SO4 / Heating 3: 91 percent / LiAlH4 / diethyl ether / Heating 4: 79 percent / pyridiniumchlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 86.5 percent / piperidine / pyridine / 24 h / 80 °C 6: 95 percent / H2 / Pd/C (10percent) / dioxane / 750.06 - 1500.1 Torr 7: polyphosphoric acid / 5 h / 80 °C 8: 97 percent / NaH / benzene / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / 1.0N aqueous NaOH / tetrahydrofuran / 20 h / 60 °C 2: oxalyl chloride / DMF / tetrahydrofuran / 1 h / 25 °C 3: tetrahydrofuran / 0.25 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / DMF / tetrahydrofuran / 1 h / 25 °C 2: tetrahydrofuran / 0.25 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: PCl5 2: ethanolic KOH | ||
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol 2.1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; palladium diacetate; 2-(3-methoxypyridin-2-yl)-4,4-dimethyl-4,5-dihydrooxazole / 1,2-dichloro-ethane / 120 °C 2.2: TABF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With formic acid; formamide at 170℃; for 6h; Stage #2: With hydrogenchloride In water at 100℃; for 1h; | 56 Reference Example 56 3.0 g of 2-acetyl-5,6,7,8-tetrahydro-naphtalene, 3.1 g of formamide and 0.34 g of formic acid were mixed, and stirred at 170 °C for 6 hours. The reaction mixture was cooled to room temperature, then water was added to it, and extracted with ethyl acetate. The oil layer was washed successively with water, concentrated under reduced pressure. The obtained residue and 36 % hydrochloric acid were mixed, and stirred at 100 °C for 1 hour. Water was added to the reaction mixture, and the product was filtered off. The product was dried under reduced pressure to obtain 2.5 g of 1-(5,6,7,8-tetrahydronaphtalene-2yl)-ethylamine hydrochloride.1H-NMR (CD3SOCD3, TMS) δ (ppm): 8.51 (3H, br.s), 7.19-7.22 (2H, m), 7.08 (1H, d, J=8.0 Hz), 4.23-4.29 (1H, m), 2.70-2.71 (4H, m), 1.72-1.74 (4H, m), 1.48 (3H, d, J=6.8 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ice-water; bromine; ethyl acetate | 53.a a a 8-bromo-6-acetyltetralin To AlCl3 (9.9 g, 75 mmol) is added dropwise 6-acetyltetralin (5.25 g, 30 mmol) under mechanical stirring at RT. After 20 minutes at 70° C. the reaction is cooled to RT and treated in small portions with Br2 (5.76 g [=1.86 ml], 36 mmol) over a period of 30 minutes. After that the mixture is stirred for further 60 minutes at 85° C. After cooling down to RT and addition of ice-water (450 ml) the compound is extracted with methylene chloride and purified on silica gel using a mixture of cyclo-hexane/ethyl acetate 2/1 to 1/1 obtaining the product as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol; diethyl ether | 3.C Step C Step C Preparation of 1-(5,6,7,8-tetrahydro-2-naphthalenyl)ethanone oxime To a solution of 6-acetyltetralin (5.0 g, 29 mmol) in methanol (30 mL) under a nitrogen atmosphere was added hydroxylamine hydrochloride (2.18 g, 32 mmol) and sodium acetate (2.59 g, 32 mmol) and the resulting mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure and the residue was taken up in diethyl ether and washed with water and then with saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford an oil which solidified. The solid was pulverized and rinsed with hexanes to afford the title compound of Step C (3.85 g) as an off-white solid. 1 H NMR (CDCl3): δ 9.1 (br s,1H), 7.33 (m,2H), 7.07 (d,1H), 2.78 (m,4H), 2.27 (s,3H), 1.79 (m,4H). | |
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 2h; Reflux; | ||
With hydroxylamine hydrochloride; sodium acetate In ethanol Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(2-chloro-ethyl)-amine In chloroform | 11 EXAMPLE 11 EXAMPLE 11 A 1M HN3 solution in chloroform (70 ml) is added to a solution of 6-acetyl-1,2,3,4-tetrahydronaphthalene(5 g) in chloroform (20 ml) and the mixture is treated with H2 SO4 (d. 1.84, 2.5 ml), added dropwise under stirring for 40 minutes. After an additional stirring for 30 minutes at room temperture the reaction mixture is washed with water, 10% aqueous K2 HPO4 and water, until the washings are neutral. The organic phase is dried on CaCl2, the solvent is evaporated in vacuum to give 4.65 g of 6-acetylamino-1,2,3,4-tetrahydro-naphthalene m.p. 105.5°-106°. I.R.=3150, 1670 cm-1. H-NMR 10.1 (s, 1H, NH); 7.1-8.0 (m, 3H, Ar); 1.7-3.1 (m+s, 11H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With ammonium acetate In ethanol for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonium acetate In butan-1-ol for 3h; Reflux; | |
65% | With ammonium acetate In butan-1-ol for 6h; Reflux; | A mixture of 6-acetyl-1,2,3,4-tetrahydronaphthalene(6.0 g, 0.034 mol), the appropriate aldehydenamely: 3,4-dimethoxybenzaldehyde and/or 4-fluorobenzaldehyde(0.034 mol), ethyl cyanoacetate (3.8mL, 0.034 mol) and ammonium acetate (21.0 g,0.272 mol) in n-butanol (50 mL) was refluxed for 6h. The formed precipitate was filtered, washed withether, dried and recrystallized from acetic acid togive the title compounds 1a,b, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ammonium acetate In butan-1-ol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 3h; Reflux; | |
With ammonium hydroxide hydrochloride; sodium acetate In ethanol; water at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydroxide In ethanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide In ethanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide In ethanol at 20 - 40℃; for 12.1667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonium acetate In butan-1-ol for 3h; Reflux; | |
With ammonium acetate In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide In ethanol at 20 - 40℃; for 12.1667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium hydroxide In ethanol at 20 - 40℃; for 12.1667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium acetate In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In toluene for 5h; Reflux; | |
58% | In toluene for 5h; Reflux; | 1 4.1.1 E-3-(N,N-dimethylamino)-1-(5,6,7,8-tetrahydronaphthalen-2-yl) prop-2-en-1-one (3) [28] To a mixture of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (1) [47] (1.74 g, 10 mmol) in dry toluene (50 mL), dimethylformamide-dimethylacetal (DMF-DMA) (1.34 g, 10 mmol) was added and the mixture was refluxed for 5 h. The solvent was evaporated and the residual reddish brown viscous liquid was taken in ether. The resulting yellow crystals were collected by filtration, washed thoroughly with ether, dried and finally recrystallized from EtOH to afford compound 3 [28] as yellow crystals in 58% yield, mp 70-72 °C; IR (KBr) (ν, cm-1): 1634 (C=O); 1H NMR (DMSO-d6): δ (ppm) 1.71 (m, 4H, aliphatic 2CH2 of tetrahydronaphthalene), 2.72 (m, 4H, aliphatic 2CH2 of tetrahydronaphthalene), 2.87 (s, 3H, CH3), 3.10 (s, 3H, CH3), 5.76 (d, 1H, J = 12.2 Hz, -CO-CH = ), 7.05-7.58 (m, 3H Ar-H), 7.65 (d, 1H, J = 12.2 Hz, =CH-N-); 13C NMR (DMSO-d6): δ (ppm) 20.12, 20.13 (2CH3), 22.48, 22.60, 28.70, 28.75 (4CH2), 90.93 (CO-CH = ), 124.25, 127.67, 128.44, 136.17, 137.52, 139.62 (Aromatic-C), 153.63 (=CH-N-), 185.70 (C=O); MS m/z (%): 229 (M+, 92.4), 212 (99.0), 159 (43.5), 98 (100), 70 (74.5). Analysis (Calc/found %): for C15H19NO (229.32): C, 78.56/78.24; H, 8.35/8.30; N, 6.11/6.28. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ammonium acetate In butan-1-ol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With ammonium acetate In butan-1-ol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 20h; Reflux; Inert atmosphere; Overall yield = 71 %; | 1.7 6.1.7 (E)-2-Hydroxy-N′-(1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)benzohydrazide (2) A mixture of 2-hydroxybenzohydrazide (0.32 g, 2.1 mmol) and 1-(5,6,7,8-tetrahydro naphthalen-2-yl)ethanone (0.36 mL, 2.1 mmol) were refluxed for 20 h in ethanol under nitrogen atmosphere. The reaction mixture was filtered and washed with warm ethanol to afford light yellow solid product (yield 71%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In ethanol for 20h; Reflux; Inert atmosphere; | 1.8 6.1.8 (E)-6-Bromo-3-hydroxy-N′-(1-(5,6,7,8-tetrahydronaphthalen-2yl)ethylidene)-2-naphthohydrazide (3) A mixture of 6-bromo-3-hydroxy-naphthohydrazide (0.59 g, 2.1 mmol) and 1-(5,6,7,8-tetrahydro naphthalen-2-yl)ethanone (0.36 mL, 2.1 mmol) were refluxed for 20 h in ethanol under nitrogen atmosphere. The reaction mixture was filtered and washed with warm ethanol to afford light yellow solid product (yield 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In ethanol for 20h; Reflux; Inert atmosphere; | 1.4 6.1.4 (E)-N′-(1-(5,6,7,8-Tetrahydronaphthalen-2-yl)ethylidene)-2-naphthohydrazide (7) A mixture of 3-hydroxy-2-naphthohydrazide (0.42 g, 2.1 mmol) and 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (0.36 mL, 2.1 mmol) were refluxed for 20 h in ethanol under nitrogen atmosphere. The reaction mixture was filtered and washed with warm ethanol to afford light yellow color solid product (yield 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In ethanol for 20h; Reflux; Inert atmosphere; | 1.1 6.1.1 (E)-3-Hydroxy-N'-(1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)-2-naphthohydrazide (HENC) A mixture of 3-hydroxy-2-naphthohydrazide (0.42 g, 2.1 mmol) and 1-(5,6,7,8-tetrahydronaphthalen-2-yl)-ethanone (0.35 mL, 2.1 mmol) were refluxed for 20 h in ethanol under nitrogen atmosphere. The reaction mixture was filtered and washed with warm ethanol to afford light yellow color solid product (yield 81%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.9 g | Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene; ethyl 2-cyanoacetate With morpholine; sulfur In toluene at 90℃; for 20h; Stage #2: With N-chloro-succinimide In chloroform at -5℃; for 3h; | 13.1; 13.2 Step1: 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (20 g, 115 mmol), ethyl 2-cyanoacetate (14.66 mL, 138 mmol), morpholine (20.08 mL, 230 mmol), and 14.72 g of sulfur were added to ethanol (115 mL) to give a yellow suspension. The reaction mixture was refluxed 20h at 90°C. Upon cooling, the reaction mixture was filtered and the solvent removed under reduced pressure. The crude brown oil was dissolved in ethyl acetate, washed with HCl 1 N, brine twice and dried over sodium sulfate. After removal of the solvent, the crude was purified over silica (dichloromethane/cyclohexane 40/60) affording 9.6 g (28%) of a yellow oil. LC/MS: purity 84%, M+1=302 Step 2: step 1 compound (9.2 g, 30.5 mmol) was dissolved in chloroform (400 mL). Upon cooling at - 5°C, N-chlorosuccinimide (4.08 g) was added and the reaction mixture was stirred for 3 hours. The reaction mixture was purified over silica (heptane/ethyl acetate 80/20) affording 2.9 g (28%) of a brown oil. NMR 1H (DMSO-d6): 0,75 (t, 3H); 1,75 (m, 4H); 2,50 (m, 4H); 3,80 (q, 2H); 6,70 (s, 1H); 6,80 (d, 1H); 7,00 (d, 1H)7,50 (bs, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene; ethyl 2-cyanoacetate With morpholine; sulfur In ethanol at 90℃; for 20h; Stage #2: With N-chloro-succinimide In chloroform at -5℃; for 3h; Stage #3: 3-pyridineacetic acid hydrochloride Further stages; | 13 2-chloro-4-hydroxy-5-(3-pyridyl)-3-tetralin-6-yl-7H-thieno[2,3-b]pyridin-6-one Step 1 : 1 -(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (20 g, 1 15 mmol), ethyl 2- cyanoacetate (14.66 mL, 138 mmol), morpholine (20.08 mL, 230 mmol), and 14.72 g of sulfur were added to ethanol (1 15 mL) to give a yellow suspension. The reaction mixture was refluxed 20h at 90 °C. Upon cooling, the reaction mixture was filtered and the solvent removed under reduced pressure. The crude brown oil was dissolved in ethyl acetate, washed with HCI 1 N, brine twice and dried over sodium sulfate. After removal of the solvent, the crude was purified over silica (dichloromethane/cyclohexane 40/60) affording 9.6 g (28%) of a yellow oil. LC/MS: purity 84%, M+1 =302 Step 2: step 1 compound (9.2 g, 30.5 mmol) was dissolved in chloroform (400 mL). Upon cooling at - 5°C, N-chlorosuccinimide (4.08 g) was added and the reaction mixture wasstirred for 3 hours. The reaction mixture was purified over silica (heptane/ethyl acetate 80/20) affording 2.9 g (28%) of a brown oil. NMR H (DMSO-d6): 0,75 (t, 3H); 1 ,75 (m, 4H); 2,50 (m, 4H); 3,80 (q, 2H); 6,70 (s, 1 H); 6,80 (d, 1 H); 7,00 (d, 1 H)7,50 (bs, 1 H) Step 3: 3-(carboxymethyl)pyridinium chloride (538 mg, 3.10 mmol) and oxalyl dichloride (0.788 mL, 9.31 mmol) and a drop of dimethylformamide were dissolved in dichloromethane (3 mL). After 2 hours, solvent was removed and dimethylformamide (4 mL) was added, followed by potassium carbonate (1 .28 g, 9.3 mmol) and step 2 compound (1 .04 g, 3.10 mmol) in dimethylformamide (8 mL). The reaction mixture was stirred overnight and poured in iced water. An ethyl acetate extraction was performed and the organic layer was washed twice with brine and dried over sodium sulfate. A brown oil (1 .25 g, 89%) was recovered after removal of the solvent. LC/MS: purity 96%, M+1 = 455 Step 4: Potassium bis(trimethylsilyl)amide (2.2 g, 1 1 mmol) was dissolved in tetrahydrofuran (5 mL) and a solution of step 3 compound (1 .25 g, 2.75 mmol) in tetrahydrofuran (9 mL) was added. After 30 minutes, a mixture of water/acetic acid was added (until pH 4) and an ethylacetate extraction was performed. The organic layer was washed twice with brine and dried over sodium sulfate. After removal of the solvent, a brown solid (0.62 g; 55%) was obtained. LC: 4.15 min, purity 99%, MS: M+1 = 409 NMR H (DMSO-d6): 1 ,76 (m, 4H); 2,74 (m, 4H); 7,06 (m, 3H); 7,34 (dd, 1 H); 7,75 (d, 1 H) 8,38 (d, 1 H); 8,51 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With hydrogenchloride In ethanol; water for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride In ethanol; water for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogenchloride In ethanol; water for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With C37H40MnN2O2P2(1+)*Br(1-); sodium t-butanolate In isopropyl alcohol at 50℃; for 3h; Inert atmosphere; Schlenk technique; enantioselective reaction; | |
37% | With potassium <i>tert</i>-butylate; cis,mer-[MnBr(CO)2(N-(2-(bis(3,5-dimethylphenyl)phosphaneyl)benzyl)-2-((diphenylphosphaneyl)oxy)cyclohexan-1-amine)]; isopropyl alcohol at 40℃; for 18h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction; | |
Multi-step reaction with 3 steps 1.1: sodium iodide / acetonitrile / 0.08 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: bis(pentafluorophenyl)borohydride; C52H58; tri-tert-butyl phosphine; hydrogen / toluene; pentane / 24 h / 50 °C / 30003 Torr / Autoclave 3.1: tetrabutyl ammonium fluoride / toluene; pentane; tetrahydrofuran / 0.5 h / 20 °C |
94 % ee | With potassium <i>tert</i>-butylate; C57H48ClFeN2O3P2(1+)*BF4(1-); isopropyl alcohol at 25℃; for 3h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In hexan-1-ol at 110℃; for 24h; Sealed tube; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 30℃; for 2.5h; Inert atmosphere; Schlenk technique; Autoclave; Glovebox; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 6-Acetyl-1,2,3,4-tetrahydronaphthalene In tetrahydrofuran for 12h; | |
21% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #2: 6-Acetyl-1,2,3,4-tetrahydronaphthalene In tetrahydrofuran; hexane at -78 - 20℃; for 14h; Inert atmosphere; | |
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 1h; Stage #2: 6-Acetyl-1,2,3,4-tetrahydronaphthalene In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 0.5h; Cooling with ice; Stage #2: 6-Acetyl-1,2,3,4-tetrahydronaphthalene In tetrahydrofuran at 25℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With iodine In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; | Typical procedure for the synthesis of 3-acylbenzothiadiazine1,1-dioxides General procedure: A mixture of acetophenone (0.040 mL,0.33 mmol), I2 (0.057 g, 0.225 mmol) and 2-aminobenzenesulfonamide(0.051 g, 0.3 mmol) in DMSO (2 mL) was stirredat 110 °C under air atmosphere in a sealed 50 mL Schlenk tubefor 24 h. After the reaction was finished, the reaction mixturewas cooled to room temperature. The resulting mixture wastaken up by dichloromethane (60 mL) and washed with saturatedNa2S2O3 solution until the brown color disappeared. Theorganic phase was dried over Na2SO4 (anhydrous), concentratedin vacuum, and the resulting residue was purified bycolumn chromatography on silica gel with EtOAc/petroleum(1:4) to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene; Benzoylacetonitrile With titanium tetrachloride In dichloromethane at 0℃; for 0.666667h; Inert atmosphere; Stage #2: With pyridine In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With iodine In dimethyl sulfoxide at 80℃; for 1h; Green chemistry; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); C21H13F3NO4PS2; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane at 20℃; for 72h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With dipotassium peroxodisulfate at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With sodium at 25 - 30℃; | General Procedure General procedure: A mixture of equimolar amounts of 2 (3.36 g, 10 mmol) and methyl aryl ketones 3a-l (10 mmol),in the appropriate alcohol (20 mL) containing sodium (0.46 g, 20 mmol) was stirred at room temperature(25-30 °C) for the proper time controlled by Thin-layer chromatography (TLC). The solid separatedwas collected, washed with water and crystallized from n-butanol to afford the title compounds 4a-x. 4-(3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)-2-methoxy-6-phenylpyridine-3-carbonitrile (4a): yield1.86 g (39.7%), m.p. 198-200 °C. IR: max/cm-1 2213 (CN), 1588, 1543 (C=N, C=C). 1H-NMR(CDCl3): δ 4.23 (s, 3H), 7.08 (s, 1H), 7.25-7.29 (m, 4H), 7.39-8.04 (m, 6H), 7.09 (d, J = 7.7 Hz, 2H), 8.04(d, J = 7.7 Hz, 2H), 8.38 (s, 1H), 8.42 (s, 1H). 13C-NMR (CDCl3): δ 54.7 93.5, 105.7, 105.8, 111.6, 111.7,114.6, 119.8, 120.0, 121.4, 123.3, 125.1, 126.7, 127.4, 127.8, 127.9, 128.4, 128.6, 128.7, 129.0, 129.7, 130.6,139.3, 154.9, 155.1, 157.8, 165.0. MS: m/z (%) 468.31 (M, 0.47). Anal. for C30H20N4O2 (468.51); Calcd. C,76.91; H, 4.30; N, 11.96. Found: C, 76.84; H, 4.26; N, 11.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.3% | With sodium at 25 - 30℃; | General Procedure General procedure: A mixture of equimolar amounts of 2 (3.36 g, 10 mmol) and methyl aryl ketones 3a-l (10 mmol),in the appropriate alcohol (20 mL) containing sodium (0.46 g, 20 mmol) was stirred at room temperature(25-30 °C) for the proper time controlled by Thin-layer chromatography (TLC). The solid separatedwas collected, washed with water and crystallized from n-butanol to afford the title compounds 4a-x. 4-(3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)-2-methoxy-6-phenylpyridine-3-carbonitrile (4a): yield1.86 g (39.7%), m.p. 198-200 °C. IR: max/cm-1 2213 (CN), 1588, 1543 (C=N, C=C). 1H-NMR(CDCl3): δ 4.23 (s, 3H), 7.08 (s, 1H), 7.25-7.29 (m, 4H), 7.39-8.04 (m, 6H), 7.09 (d, J = 7.7 Hz, 2H), 8.04(d, J = 7.7 Hz, 2H), 8.38 (s, 1H), 8.42 (s, 1H). 13C-NMR (CDCl3): δ 54.7 93.5, 105.7, 105.8, 111.6, 111.7,114.6, 119.8, 120.0, 121.4, 123.3, 125.1, 126.7, 127.4, 127.8, 127.9, 128.4, 128.6, 128.7, 129.0, 129.7, 130.6,139.3, 154.9, 155.1, 157.8, 165.0. MS: m/z (%) 468.31 (M, 0.47). Anal. for C30H20N4O2 (468.51); Calcd. C,76.91; H, 4.30; N, 11.96. Found: C, 76.84; H, 4.26; N, 11.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.8% | With sodium hydride In 1,4-dioxane; toluene; mineral oil at 80℃; | 3 4.1.3 General procedure for the synthesis of aryl ethyl acetate derivatives 9-12 General procedure: As a typical procedure, the preparation of aryl ethyl acetate derivative 9 is described in detail. 2.36g (98.33mmol) of NaH 60% dispersion in mineral oil was placed in a 100mL round-bottomed flask and washed with toluene to remove oil. Then, 7.12mL (59.75mmol, d=0.975g/mL) of diethyl carbonate and 20mL of anhydrous dioxane were added. The mixture was heated to 80°C with stirring and then 4.46mL (29.37mmol, d=1.120g/mL) of 1-acetyl naphthalene was added dropwise. The mixture was stirred at 80°C for 15h and monitored by TLC analysis (eluent ethyl acetate/petroleum ether, 1:5). The reaction mixture was allowed to cool to room temperature, and 25mL of water was added. The water layer was separated and extracted twice with ethyl acetate. The organic layers were combined and washed with water and brine, dried over Na2SO4, filtered, and evaporated to dryness, giving 5.73g of a yellow oil. The crude product was used for the next reaction step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With sodium tetrahydroborate In tetrahydrofuran; methanol at 23℃; for 0.5h; Inert atmosphere; Stage #2: chloro-trimethyl-silane With triethylamine In dichloromethane at 23℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With triethylamine In dichloromethane at 20 - 25℃; for 1h; Inert atmosphere; Stage #2: t-butyldimethylsiyl triflate In dichloromethane at 20 - 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium phosphate; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; potassium hydroxide at 90℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dipotassium peroxodisulfate; cobalt(III) acetylacetonate; silver(I) acetate at 130℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / Inert atmosphere; Sealed tube 2: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / Inert atmosphere; Sealed tube 2: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube 3: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.6 %Chromat. | With tetrabutylammonium perchlorate; water; sodium acetate In acetonitrile Electrochemical reaction; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 6-Acetyl-1,2,3,4-tetrahydronaphthalene With pyridine; selenium(IV) oxide at 110℃; for 20h; Inert atmosphere; Stage #2: methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With iodine; N-aminopyridin-1-ium iodide; toluene-4-sulfonic acid hydrazide In dimethyl sulfoxide at 90℃; for 1h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With anhydrous tin tetrachloride In toluene at 0℃; for 12h; Reflux; |
Tags: 774-55-0 synthesis path| 774-55-0 SDS| 774-55-0 COA| 774-55-0 purity| 774-55-0 application| 774-55-0 NMR| 774-55-0 COA| 774-55-0 structure
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P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
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 |
Sorry,this product has been discontinued.
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