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[ CAS No. 24945-13-9 ]

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Chemical Structure| 24945-13-9
Chemical Structure| 24945-13-9
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CAS No. :24945-13-9 MDL No. :MFCD01549685
Formula : C7H14O2 Boiling Point : 205.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :130.18 g/mol Pubchem ID :-
Synonyms :

Safety of [ 24945-13-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24945-13-9 ]

  • Downstream synthetic route of [ 24945-13-9 ]

[ 24945-13-9 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 627-27-0 ]
  • [ 67-64-1 ]
  • [ 24945-13-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 3
  • [ 1194-16-7 ]
  • [ 24945-13-9 ]
YieldReaction ConditionsOperation in experiment
89% With methanol; sodium tetrahydroborate at 0 - 20℃; for 3h; 256.1 Step 1. To a 500 mL round-bottom flask was added 2,2-dimethyloxan-4-one 329a (10 g,78.02 mmol, 1.00 equiv.) and methanol (100 mL). NaBH4 (5.9 g, 155.96 mmol, 2.00 equiv.)5 was added in several batches at 0°C. The resulting mixture vas stirred at room temperaturefor 3 h, then diluted with 200 mL of EA, vvashed vvith brine (l 00 mL x 2), dried overanhydrous sodium sulfate, and concentrated under vacuum The residue vvas purified by silicagel column chromatography eluting with ethyl acetate in petroleum ether (0% tolOO%) togive 2,2-dirnethyloxan-4-ol 329b (9 g, 89%) as a light yellow oil.
89% With sodium tetrahydroborate In methanol at 0 - 20℃; for 3h; 24.1 Example 24: 4-1(1 S,4S,5R)-5-{j4-cyclopropyl-1-(2,6-dichlorophenyl)-1H-pyrazol-5- ylJ methoxy}-2-azabicyclo 12.2.11 heptan-2-ylJ-N- j(2,2-dimethyloxan-4-yl)sulfonylj benzamide (1-21) To a 500 mL round-bottom flask was added 2,2-dimethyloxan-4-one 21a (10 g, 78.02 mmol, 1.00 equiv.) and methanol (100 mL). NaBH4 (5.9 g, 155.96 mmol, 2.00 equiv.) was added in several batches at 0°C. The resulting mixture was stirred at room temperature for 3 h, then diluted with 200 mL of EA, washed with brine (100 mL x 2), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate in petroleum ether (0% to 100%) to give 2,2- dimethyloxan-4-ol 21b (9 g, 89%) as a light yellow oil.
With sodium tetrahydroborate In ethanol Yield given;
With methanol; sodium tetrahydroborate at 20℃; for 3h; Cap- 188, step aTo a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2 g, 15.60 mmol) in 50 niL of MeOH was slowly added sodium borohydride (0.649 g, 17.16 mmol). The resulting mixture was stirred at room temperature for 3 hours. To the mixture was then added 1 N HCl aqueous solution until it crosses into acidic pH range and then extracted with EtOAc (3X). The combined organic layers were dried withMgS04 and concentrated to afford Cap-188, step a (1.9 g) as clear oil. The product was used in the next step without purification. XH NMR (400 MHz, CDCI3) δ ppm 3.91 - 4.02 (1 H, m), 3.79 - 3.86 (1 H, m), 3.63 (1 H, td, J=12.05, 2.51 Hz), 1.82 - 1.93 (2 H, m), 1.40 - 1.53 (1 H, m), 1.29 - 1.38 (1 H, m), 1.27 (3 H, s), 1.20 (3 H, s)

YieldReaction ConditionsOperation in experiment
Aus 2.2-Dimethyl-pyron-(4), Hydrieren in 25percentig. NH3 bei 80 atm Anfangsdruck u. 75-80 min (neben anderen Verbb.);
  • 5
  • [ 627-27-0 ]
  • [ 7664-93-9 ]
  • [ 67-64-1 ]
  • [ 24945-13-9 ]
  • 6
  • [ 109752-89-8 ]
  • [ 24945-13-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaIO4 / H2O / 1 h 2: NaBH4 / aq. ethanol
  • 7
  • 2,5-di(3',3'-dimethyl-4'-oxacyclohexano)dioxolane [ No CAS ]
  • [ 24945-13-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / 80percent AcOH / 1.5 h / Heating 2: NaIO4 / H2O / 1 h 3: NaBH4 / aq. ethanol
  • 8
  • [ 24945-13-9 ]
  • [ 1028745-80-3 ]
  • [ 530-62-1 ]
  • [ 1028719-07-4 ]
YieldReaction ConditionsOperation in experiment
41% Stage #1: 2,2-dimethyltetrahydropyran-4-ol; 4'-[2-ethyl-1-(4-hydroxyphenyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene for 2h; Stage #2: With hydroxylamine hydrochloride; sodium hydrogencarbonate In dimethyl sulfoxide at 90℃; Stage #3: 1,1'-carbonyldiimidazole With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 1 - 30℃; for 0.5h; 413 To a solution of 4' -{ [2-ethyl-l- (4-hydroxyphenyl) -6-oxo- 4-propyl-l, 6-dihydropyrimidin-5-yl] methyl }biphenyl-2- carbonitrile (0.9 g) , 2,2-dimethyltetrahydro-2H-pyran-4-ol (0.78 g) and triphenylphosphine (1.6 g) in tetrahydrofuran (9 mL) was added dropwise diisopropyl azodicarboxylate (1.9 M toluene solution, 3.2 mL) . After stirring for 2 hr, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and a mixture of the residue, hydroxylammonium chloride (1.4 g) , sodium hydrogen carbonate(2 g) and dimethyl sulfoxide (10 mL) was stirred overnight at 9O0C. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL) . N,N' -carbonyldiimidazole (0.48 g) and then 1, 8-diazabicyclo [5.4.0] undec-7-ene (0.45 mL) were added, and the mixture was stirred at room temperature for' 30 min. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (0.51 g, 41%) as an amorphous solid. 1H NMR (300 MHz, DMSO-d6) δ 0.90 (3 H, t, J=7.4), 1.05 (3 H, t, J=7.4), 1.20 (3 H, s), 1.24 (3 H, s) , 1.34 - 1.67 (4 H, m) , 1.92 - 2.07 (2 H, m) , 2.28 (2 H, q, J=7.6), 2.47 - 2.57 (2 H, m) , 3.60 - 3.81 (2 H, m) , 3.86 (2 H, s) , 4.68 - 4.83 (1 H, m) , 7.04 - 7.13 (2 H, m) , 7.18 - 7.31 (6 H, m) , 7.47 - 7.58 (2 H, m) , 7.61 - 7.74 (2 H, m) , 12.39 (1 H, s)
  • 9
  • [ 24945-13-9 ]
  • [ 61-82-5 ]
  • [ 1239270-24-6 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2,2-dimethyltetrahydropyran-4-ol With dipyridinium dichromate In tetrahydrofuran at 20℃; for 3h; Molecular sieve; Stage #2: 3(5)-amino-1,2,4-triazole With sodium cyanoborohydride; acetic acid at 20℃; for 16h; 115 Reference Example 115N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4H-1,2,4-triazol-3-amineA mixture of 2,2-dimethyltetrahydro-2H-pyran-4-ol (5 g), pyridinium dichromate (22 g), molecular sieves 4 A (22 g) and tetrahydrofuran (200 mL) was stirred at room temperature for 3 hr. The reaction solution was diluted with diethyl ether (200 mL), the insoluble material was filtered off through silica gel, and the filtrate was concentrated. The obtained residue was dissolved in acetic acid (30 mL), 1H-1,2,4-triazol-3-amine (2.2 g) and sodium cyanoborohydride (11 g) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.8 g, 60%).1H NMR (300 MHz, DMSO-d6) δ 1.09-1.33 (m, 8H), 1.71-1.88 (m, 2H), 3.51-3.70 (m, 3H), 5.42-6.47 (m, 1H), 7.22-8.07 (m, 1H), 11.97-12.81 (m, 1H)
  • 10
  • [ 24945-13-9 ]
  • [ 4923-01-7 ]
  • [ 1239270-28-0 ]
YieldReaction ConditionsOperation in experiment
49% Stage #1: 2,2-dimethyltetrahydropyran-4-ol With dipyridinium dichromate In tetrahydrofuran at 20℃; for 3h; Molecular sieve; Stage #2: 5-methyl-4H-1,2,4-triazol-3-amine With sodium cyanoborohydride; acetic acid at 20℃; for 16h; 119 Reference Example 119N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5-methyl-4H-1,2,4-triazol-3-amineA mixture of 2,2-dimethyltetrahydro-2H-pyran-4-ol (5 g), pyridinium dichromate (22 g), molecular sieves 4 A (22 g) and tetrahydrofuran (200 mL) was stirred at room temperature for 3 hr. The reaction solution was diluted with diethyl ether (200 mL), the insoluble material was filtered off through silica gel, and the filtrate was concentrated. The obtained residue was dissolved in acetic acid (30 mL), 5-methyl-4H-1,2,4-triazol-3-amine (2.5 g) and sodium cyanoborohydride (11 g) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.6 g, 49%).1H NMR (300 MHz, DMSO-d6) δ 1.03-1.30 (m, 8H), 1.70-1.85 (m, 2H), 2.07 (br.s., 3H), 3.48-3.66 (m, 3H), 5.17-6.39 (m, 1H), 11.47-12.45 (m, 1H)
  • 11
  • [ 24945-13-9 ]
  • [ 98-59-9 ]
  • [ 1307304-82-0 ]
  • [ 1307304-83-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 20℃; for 48h; Cap-188.1 and Cap-188.2, step bp-Tosyl-Cl (5.56 g, 29.2 mmol) was added to a solution of Cap-188, step a (1.9 g, 14.59 mmol) and pyridine (4.72 mL, 58.4 mmol) in 100 mL of CH2C12. The resulting mixture was stirred at room temperature for 3 days. To the reaction was added 10 mL of water, and the mixture was stirred at room temperature for an additional hour. The two layers were separated and the organic phase was washed with water and 1 N HCl aqueous solution. The organic phase was dried with MgS04 and concentrated to afford the mixture of two enantiomers as a light yellow solid. The mixture was then separated by chiral HPLC (CHIRALPAK AD column, 21 x 250 mm, 10 urn) eluting with 92% 0.1%diethylamine/Heptane-8% EtOH at 15 mL/min to afford Cap-188. 1, step b (1.0 g) and Cap-188.2, step b (1.0 g). The absolute stereochemistry of the two enantiomers was not assigned. Cap-188. 1, step b: LC-MS: Anal. Calcd. for [2M+Na]+ 591.21; found 591.3. ¾ NMR (500 MHz, CDC13) δ ppm 7.79 (2 H, d, J=8.24 Hz), 7.34 (2 H, d, J=8.24 Hz), 4.72 - 4.81 (1 H, m), 3.78 (1 H, dt, J=12.44, 4.16 Hz), 3.53 - 3.61 (1 H, m), 2.45 (3 H, s), 1.75 - 1.86 (2 H, m), 1.61 - 1.71 (1 H, m), 1.52 - 1.60 (1 H, m), 1.22 (3 H, s), 1.14 (3H, s). Cap-188.2, step b: LC-MS: Anal. Calcd. for [2M+Na]+ 591.21 ; found 591.3.
  • 12
  • [ 24945-13-9 ]
  • [ 124-63-0 ]
  • 2,2-dimethyloxan-4-yl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; 256.2 Step 2. To a 500 mL round-bottom flask purged with and maintained under an inertatmosphere of nitrogen was added a solution of 22-dimethyloxan-4-ol 329b (9 g, 69.13mmol, 1.00 equiv.) in dichloromethane (200 mL) followed byTEA (7.69 g, 76.00 mmol, 1.10equiv.). The mixture was cooled to 0°C, MsCl (8.68 g, 76.14 mmol, 1.10 equiv.) was added15 drop'.vise with stirring. The resulting mixture was stirred at room temperature for 2h. Themixtme wa;;; diluted with DCM (200 mL), washed with brine (100 mL x 2), dried overanhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silicagel column chromatography eluting vvith ethyl acetate in petroleum ether (O~o to 30%) to give22-dimethyloxan-4-yl methanesulfonate 329c (l4g, 97%) as a white solid.
97% With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; 24.2 To a 500 mL round-bottom flask purged with and maintained under an inert atmosphere of nitrogen was added a solution of 2,2-dimethyloxan-4-ol 21b (9 g, 69.13 mmol, 1.00 equiv.) in dichloromethane (200 mL) followed byTEA (7.69 g, 76.00 mmol, 1.10 equiv.). The mixture was cooled to 0°C, MsCl (8.68 g, 76.14 mmol, 1.10 equiv.) was added dropwise with stirring. The resulting mixture was stirred at room temperature for 2h. The mixture was diluted with DCM (200 mL), washed with brine (100 mL x 2), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate in petroleum ether (0% to 30%) to give 2,2-dimethyloxan-4-yl methanesulfonate 21c (14g, 97%) as a white solid.
  • 13
  • [ 24945-13-9 ]
  • 4-[(1S,4R,5R)-5-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}-3-oxo-2-azabicyclo[2.2.1]heptan-2-yl]-N-[(2,2-dimethyloxan-4-yl)sulfonyl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: N-chloro-succinimide; hydrogenchloride / water; acetonitrile / 0.17 h / 0 °C 4: ammonia / tetrahydrofuran / 2 h / 0 °C 5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C
  • 14
  • [ 24945-13-9 ]
  • 1-[(2,2-dimethyloxan-4-yl)sulfanyl]ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
  • 15
  • [ 24945-13-9 ]
  • 2,2-dimethyloxane-4-sulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: N-chloro-succinimide; hydrogenchloride / water; acetonitrile / 0.17 h / 0 °C
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: N-chloro-succinimide; hydrogenchloride / water; acetonitrile / 0.17 h / 0 °C
  • 16
  • [ 24945-13-9 ]
  • 2,2-dimethyloxane-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: N-chloro-succinimide; hydrogenchloride / water; acetonitrile / 0.17 h / 0 °C 4: ammonia / tetrahydrofuran / 2 h / 0 °C
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: N-chloro-succinimide; hydrogenchloride / water; acetonitrile / 0.17 h / 0 °C 4: ammonia / tetrahydrofuran / 2 h / 0 °C
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