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CAS No. : | 169899-49-4 | MDL No. : | MFCD23105985 |
Formula : | C7H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KFLCCZPFOPDGLN-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 45090007 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.84 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.96 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | 0.32 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 0.77 |
Consensus Log Po/w : | 0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.8 |
Solubility : | 23.0 mg/ml ; 0.16 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 20.4 mg/ml ; 0.141 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.61 |
Solubility : | 35.2 mg/ml ; 0.244 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.6 |
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 |
---|---|---|
With sodium tetrahydroborate; ozone Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrachloromethane; triphenylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine at 0℃; for 1.16667h; | 7.1 Step 1: Step 1: Synthesis of methyl 1-methyl-3-((methylsulfonyl)oxy)cyclobutane-1-carboxylate Methanesulfonyl chloride (0.60 mL, 7.6 mmol) was added to a solution of methyl 3-hydroxy-1-methylcyclobutane-1-carboxylate (1.00 g, 6.94 mmol) and triethylamine (1.26 mL, 9.02 mmol) at 0° C. After the addition, the cooling bath was removed and the reaction mixture was stirred for 70 min. The reaction mixture was then partitioned between DCM and aqueous hydrochloric acid solution (1 N). The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, and then was dried over sodium sulfate. The mixture was then filtered, and the filtrate was concentrated to give methyl 1-methyl-3-((methylsulfonyl)oxy)cyclobutane-1-carboxylate (1.48 g, 96%) as a light yellow oil that was used in the next step without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 1.17 h / 0 °C 2: sodium iodide / N,N-dimethyl-formamide / 46 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / 1.17 h / 0 °C 2.1: sodium iodide / N,N-dimethyl-formamide / 46 h / 80 °C 3.1: zinc / N,N-dimethyl acetamide; tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; sodium tetrahydroborate for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 5h; | 1.A.1 Step 1 : To a solution of S10 (Trifluoroacetate salt) (60 mg, 0.098 mmol) and methyl 3 -hydroxy- 1-methyl-cyclobutanecarboxylate (35.4 mg, 0.245 mmol) in DMF (1 mL) was added NaH (7.8 mg, 0.196 mmol) at 0 °C, the solution was stirred at this temperature for 1 hours and then 4 hours at room temperature. After this time, LCMS shows complete consumption of starting material. This reaction mixture was directly carried forward to the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 4: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trimethyl phosphite / dichloromethane / Inert atmosphere; Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 4: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trimethyl phosphite / dichloromethane / Inert atmosphere; Irradiation 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 4: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trimethyl phosphite / dichloromethane / Inert atmosphere; Irradiation 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 6: N-Methyldicyclohexylamine; bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 4: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trimethyl phosphite / dichloromethane / Inert atmosphere; Irradiation 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 6: N-Methyldicyclohexylamine; bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 110 °C / Inert atmosphere 7: methanol; sodium hydroxide / tetrahydrofuran / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 4: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trimethyl phosphite / dichloromethane / Inert atmosphere; Irradiation 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 6: N-Methyldicyclohexylamine; bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 110 °C / Inert atmosphere 7: methanol; sodium hydroxide / tetrahydrofuran / 3 h / 50 °C 8: hydrogen; palladium 10% on activated carbon / methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1H-imidazole In dichloromethane at 20℃; | 1.B.1 Step 1: methyl 3-((tert-butyldimethylsilyl)oxy)-l-methylcyclobutane-l-carboxylate (C431) To a solution of methyl 3 -hydroxy- 1-methylcy cl obutane-l-carboxylate (5 g, 34.68 mmol) in DCM (74 mL) was added TBSC1 (6.3 g, 41.80 mmol) and imidazole (2.8 g, 41.13 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water, and the organic phase was concentrated in vacuo. Purification by silica gel chromatography (0-35% EtOAc in Heptane) afforded methyl 3-((tert- butyldimethylsilyl)oxy)- 1-methylcy cl obutane-l-carboxylate C431 (6.7 g, 75%). 'H NMR (400 MHz, Chloroform-d) 54.37 - 4.16 (m, 1H), 3.66 (dd, J = 4.5, 1.3 Hz, 3H), 2.71 (ddd, J = 10.0, 5.7, 2.1 Hz, 1H), 2.34 (ddd, J = 9.8, 7.7, 2.8 Hz, 1H), 2.17 (ddd, J = 9.5, 7.0, 2.8 Hz, 1H), 1.85 (ddd, J = 9.9, 7.1, 2.8 Hz, 1H), 1.36 (d, J = 1.4 Hz, 1H), 1.32 (s, 1H), 0.84 (s, 9H). |
75% | With 1H-imidazole In dichloromethane at 20℃; | 1.B.1 Step 1: methyl 3-((tert-butyldimethylsilyl)oxy)-l-methylcyclobutane-l-carboxylate (C431) To a solution of methyl 3 -hydroxy- 1-methylcy cl obutane-l-carboxylate (5 g, 34.68 mmol) in DCM (74 mL) was added TBSC1 (6.3 g, 41.80 mmol) and imidazole (2.8 g, 41.13 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water, and the organic phase was concentrated in vacuo. Purification by silica gel chromatography (0-35% EtOAc in Heptane) afforded methyl 3-((tert- butyldimethylsilyl)oxy)- 1-methylcy cl obutane-l-carboxylate C431 (6.7 g, 75%). 'H NMR (400 MHz, Chloroform-d) 54.37 - 4.16 (m, 1H), 3.66 (dd, J = 4.5, 1.3 Hz, 3H), 2.71 (ddd, J = 10.0, 5.7, 2.1 Hz, 1H), 2.34 (ddd, J = 9.8, 7.7, 2.8 Hz, 1H), 2.17 (ddd, J = 9.5, 7.0, 2.8 Hz, 1H), 1.85 (ddd, J = 9.9, 7.1, 2.8 Hz, 1H), 1.36 (d, J = 1.4 Hz, 1H), 1.32 (s, 1H), 0.84 (s, 9H). |