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[ CAS No. 150668-37-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 150668-37-4
Chemical Structure| 150668-37-4
Chemical Structure| 150668-37-4
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Product Details of [ 150668-37-4 ]

CAS No. :150668-37-4 MDL No. :MFCD03841207
Formula : C11H12O Boiling Point : -
Linear Structure Formula :- InChI Key :BKPSILXHXNLDKJ-UHFFFAOYSA-N
M.W : 160.21 Pubchem ID :21431776
Synonyms :

Calculated chemistry of [ 150668-37-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.1
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.52
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 2.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.308 mg/ml ; 0.00192 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.386 mg/ml ; 0.00241 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0765 mg/ml ; 0.000478 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 150668-37-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 150668-37-4 ]

* 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 [ 150668-37-4 ]

[ 150668-37-4 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 40877-15-4 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide In methanol for 12h; Ambient temperature;
  • 2
  • [ 5293-84-5 ]
  • [ 150668-37-4 ]
  • (Z)-β-Chloro-α-cyclopropyl-m-methylstyrene [ No CAS ]
  • (E)-β-Chloro-α-cyclopropyl-m-methylstyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37 % Spectr. 2: 63 % Spectr. With piperidine; n-butyllithium In diethyl ether; hexane 1.) room temp., 4 h, 2.) room temp., overnight; Title compound not separated from byproducts;
  • 3
  • [ 591-17-3 ]
  • [ 4023-34-1 ]
  • [ 10108-64-2 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; magnesium 3 Cyclopropyl m-tolyl ketone Cyclopropyl m-tolyl ketone m-Bromotoluene (34.2 g) in dry ether (120 ml) was added dropwise to magnesium turnings (4.8 g) in dry ether (100 ml). The heat of reaction maintained the mixture to boiling under reflux during the addition and the mixture was heated under reflux for a further hour. The mixture was cooled to 0°, dry cadmium chloride (19.6 g) was added and the temperature allowed to rise to 20° C. After 1 hour, cyclopropanecarbonyl chloride (20.8 g) in dry ether (50 ml) was added dropwise and the mixture was heated under reflux for 4 hours, cooled to 0° and treated with 2 N hydrochloric acid. The ether layer was separated, washed with aqueous sodium bicarbonate (3* 100 ml., 8%) and with water, dried over magnesium sulphate, filtered and evaporated. The residue was distilled under reduced pressure and the fraction b.p. 86°-90°/0.4 mm was collected.
  • 4
  • [ 150668-37-4 ]
  • α-Bromo-m-tolyl cyclopropyl ketone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In tetrachloromethane 3 α-Bromo-m-tolyl cyclopropyl ketone α-Bromo-m-tolyl cyclopropyl ketone A stirred suspension of cyclopropyl m-tolyl ketone (16 g) and N-bromosuccinimide (17.8 g) in carbon tetrachloride (100 ml) was irradiated and heated under reflux by means of a tungsten lamp for 2 hours and cooled. The solid was filtered off and the filtrate evaporated. The residual oil was distilled under reduced pressure and the fraction distilling at 115°-130°/0.1 mm was collected.
  • 5
  • [ 150668-37-4 ]
  • [ 1432048-22-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2.1: methanol / 48 h / 35 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: 0.25 h / -78 °C 3.3: 0.5 h / 50 - 60 °C 4.1: methanol; sodium tetrahydroborate / 20 °C
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2.1: methanol / 48 h / 35 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: 0.25 h / -78 °C 3.3: 0.5 h / 50 - 60 °C 4.1: sodium tetrahydroborate / methanol / 20 °C
  • 6
  • [ 150668-37-4 ]
  • [ 40877-15-4 ]
YieldReaction ConditionsOperation in experiment
50% With pyridine hydrochloride; toluene-4-sulfonic acid In acetonitrile at 160℃; for 3h; Microwave irradiation; 91B Example 91B Example 91B 4-chloro-1-m-tolylbutan-1-one A solution of Example 91A (2.56 g, 16.9 mmol), TsOH.H2O (3.2 g, 16.9 mmol) and pyridine hydrochloride (3.88 g, 33.8 mmol) in CH3CN (60 mL) was heated at 160° C. for 3 hours under microwave and the CH3CN was removed by reduced pressure to give a residue, which was re-dissolved in ethyl acetate (100 mL). The resulting organic solution was washed with aqueous NaHCO3 (50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated to give a black oil. The oil was purified by chromatography on silica gel column (petroleum ether: ethyl acetate=20:1) to give the title compound (1.56 g, 50%). LC-MS (M+H): m/z 197. 1H NMR (400 MHz, CDCl3): δ ppm 7.765-7.786 (m, 2H), 7.354-7.397 (m, 2H), 3.679 (t, J=6.2 Hz, 2H), 3.170 (t, J=6.2 Hz, 2H), 2.419 (s, 3H), 2.194-2.260 (m, 2H).
50% With pyridine hydrochloride; toluene-4-sulfonic acid In acetonitrile at 160℃; for 3h; Microwave irradiation; 91B 4-chloro- 1 -m-tolylbutan- 1 -one 4-chloro- 1 -m-tolylbutan- 1 -one[136] A solution of Example 91A (2.56 g, 16.9 mmol), TsOH.H20 (3.2 g, 16.9 mmol) and pyridine hydrochloride (3.88 g, 33.8 mmol) in CH3CN (60 mL) was heated at 160 °C for 3 hours under microwave and the CH3CN was removed by reduced pressure to give a residue, which was re-dissolved in ethyl acetate (100 mL). The resulting organic solution was washed with aqueous NaHCC^ (50 mL) and brine (50 mL), dried over MgS04, filtered, and concentrated to give a black oil. The oil was purified bychromatography on silica gel column (petroleum ether: ethyl acetate =20: 1) to give the title compound (1.56 g, 50%). LC-MS (M+H): m/z 197. XH NMR (400 MHz, CDC13): ? ppm 7.765-7.786 (m, 2H), 7.354-7.397 (m, 2H), 3.679 (t, J=6.2Hz, 2H), 3.170 (t, J=6.2Hz, 2H), 2.419 (s, 3H), 2.194-2.260 (m, 2H).
  • 7
  • [ 150668-37-4 ]
  • [ 1432492-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2: methanol / 48 h / 35 °C
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2: methanol / 48 h / 35 °C
  • 8
  • [ 150668-37-4 ]
  • [ 1432492-66-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2.1: methanol / 48 h / 35 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: 0.25 h / -78 °C 3.3: 0.5 h / 50 - 60 °C
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid; pyridine hydrochloride / acetonitrile / 3 h / 160 °C / Microwave irradiation 2.1: methanol / 48 h / 35 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: 0.25 h / -78 °C 3.3: 0.5 h / 50 - 60 °C
  • 9
  • [ 23719-80-4 ]
  • [ 135754-82-4 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 0 - 20℃; for 4h; 91A Example 91A Example 91A cyclopropyl(m-tolyl)methanone To a solution of N-methoxy-N,3-dimethylbenzamide (2.86 g, 16 mmol) in THF (50 mL) was added cyclopropylmagnesium bromide (2 N in THF, 40 mmol, 20 mL) dropwise at 0° C. After addition, the reaction mixture was stirred for 4 hours at room temperature and quenched with 30 mL of aqueous NH4Cl. The aqueous phase was separated and extracted with ethyl acetate (50 mL*2). The combined organic phase was washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated to give crude product as a yellow oil (2.56 g, 100%). LC-MS (M+H): m/z 161. 1H NMR (400 MHz, CDCl3): δ ppm 7.817 (s, 2H), 7.367-7.332 (m, 2H), 2.697-2.635 (m, 1H), 2.417 (s, 3H), 1.247-1.209 (m, 2H), 1.046-1.000 (m, 2H).
In tetrahydrofuran at 0 - 20℃; for 4h; 91A cyclopropyl(m-tolyl)methanone cyclopropyl(m-tolyl)methanone[134] To a solution of N-methoxy-N,3 -dimethylbenzamide (2.86 g, 16 mmol) in THF (50 mL) was added cyclopropylmagnesium bromide (2 N in THF, 40 mmol, 20 mL) dropwise at 0 °C. After addition, the reaction mixture was stirred for 4 hours at room temperature and quenched with 30 mL of aqueous NH4C1. The aqueous phase was separated and extracted with ethyl acetate (50 mLx2). The combined organic phase was washed with water (50 mL), brine (50 mL), dried over Na2S04; filtered, and concentrated to give crude product as a yellow oil (2.56 g, 100%). LC-MS (M+H): m/z 161. XH NMR (400 MHz, CDCI3): ? ppm 7.817 (s, 2H), 7.367-7.332 (m, 2H), 2.697-2.635 (m , 1H), 2.417 (s, 3H), 1.247-1.209 (m,2H), 1.046- 1.000 (m, 2H).
  • 10
  • C18H18F3IO4S [ No CAS ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry 2: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry
  • 11
  • C12H13F3O4S [ No CAS ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
37.6 mg In dichloromethane at -50℃; for 6h; Inert atmosphere; Schlenk technique; Green chemistry;
  • 12
  • 1-(1-(m-tolyl)vinyl)cyclobutan-1-ol [ No CAS ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry 2: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry 3: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry
  • 13
  • [ 28987-79-3 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry 3: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry 4: dichloromethane / 6 h / -50 °C / Inert atmosphere; Schlenk technique; Green chemistry
  • 14
  • [ 150668-37-4 ]
  • 1,1-diethyl-4-(m-tolyl)silinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C 1.2: -78 - 20 °C 2.1: trityl tetrakis(pentafluorophenyl)borate / chlorobenzene / 0.17 h / 20 °C / Glovebox
  • 15
  • [ 1779-49-3 ]
  • [ 150668-37-4 ]
  • 1-(1-cyclopropylvinyl)-3-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Stage #2: Cyclopropyl m-methylphenyl ketone In tetrahydrofuran at -78 - 20℃;
  • 16
  • [ 591-17-3 ]
  • [ 147356-78-3 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-3-methylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: cyclopropanecarboxylic acid N-methoxy-N-methylamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
Stage #1: 1-bromo-3-methylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: cyclopropanecarboxylic acid N-methoxy-N-methylamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
  • 17
  • [ 13633-25-5 ]
  • [ 150668-37-4 ]
  • C21H26O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With methanol; nickel(II) bromide ethylene glycol dimethyl ether; bathophenanthroline; zinc powder at 60℃; for 24h; regioselective reaction;
  • 18
  • [ 103-63-9 ]
  • [ 150668-37-4 ]
  • 6-phenyl-1-(m-tolyl)hexan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 5,5'-dimethyl-2,2'-bipyridine; Ni(ClO4)2·6H2O; zinc In N,N-dimethyl acetamide at 25 - 40℃; for 12h; Inert atmosphere; Microwave irradiation; regioselective reaction;
  • 19
  • [ 150668-37-4 ]
  • [ 944344-73-4 ]
YieldReaction ConditionsOperation in experiment
65% With palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Sealed tube; stereoselective reaction;
  • 20
  • C11H14O [ No CAS ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
With Dess-Martin periodane In dichloromethane at 20℃; for 0.25h; Inert atmosphere;
  • 21
  • [ 620-23-5 ]
  • [ 150668-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
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