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[ CAS No. 169899-49-4 ] {[proInfo.proName]}

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Chemical Structure| 169899-49-4
Chemical Structure| 169899-49-4
Structure of 169899-49-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 169899-49-4 ]

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 :

Calculated chemistry of [ 169899-49-4 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 169899-49-4 ]

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:

Application In Synthesis of [ 169899-49-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 169899-49-4 ]

[ 169899-49-4 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 15760-37-9 ]
  • [ 169899-49-4 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; ozone Multistep reaction;
  • 2
  • [ 169899-49-4 ]
  • [ 1378675-95-6 ]
YieldReaction ConditionsOperation in experiment
With tetrachloromethane; triphenylphosphine
  • 3
  • [ 124-63-0 ]
  • [ 169899-49-4 ]
  • [ 2133403-08-2 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 169899-49-4 ]
  • [ 2133403-20-8 ]
YieldReaction ConditionsOperation 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
  • 5
  • [ 169899-49-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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
  • 6
  • [ 98-59-9 ]
  • [ 169899-49-4 ]
  • [ 2411494-89-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;
  • 7
  • [ 1408075-88-6 ]
  • [ 169899-49-4 ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium tetrahydroborate for 0.5h; Inert atmosphere;
  • 8
  • [ CAS Unavailable ]
  • [ 169899-49-4 ]
  • [ 2718158-16-6 ]
YieldReaction ConditionsOperation 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.
  • 9
  • [ 169899-49-4 ]
  • [ 2721393-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 20 °C 2: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C
  • 10
  • [ 169899-49-4 ]
  • [ 2721393-05-9 ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 169899-49-4 ]
  • [ 2721393-06-0 ]
YieldReaction ConditionsOperation 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
  • 12
  • [ 169899-49-4 ]
  • [ 2721393-07-1 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 169899-49-4 ]
  • [ 2721393-08-2 ]
YieldReaction ConditionsOperation 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
  • 14
  • [ 169899-49-4 ]
  • [ 2721393-09-3 ]
YieldReaction ConditionsOperation 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
  • 15
  • [ 169899-49-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 18162-48-6 ]
  • [ 169899-49-4 ]
  • [ 2721393-03-7 ]
YieldReaction ConditionsOperation 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).
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