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6-acetamido-2-fluoromethyl-3-(2-methylphenyl)-4(3H)-1,3-phthalazinone
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 70℃; for 2h; | 88.5% |
2-fluoromethyl-3-(o-hydroxymethylphenyl)-6-nitro-4(3H)-quinazolinone
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With stannous chloride In hydrogenchloride; methanol; chloroform; water; isopropyl alcohol | 84% |
With hydrogenchloride; palladium-carbon In hydrogen | 72% |
With acetic acid; palladium-carbon In chloroform; hydrogen | 52.5% |
isatoic anhydride
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid; nitric acid / 2 h / 0 - 10 °C 2.1: hydrogen / tetrahydrofuran / 2 h / 60 °C / 15001.5 Torr 2.2: 1 h / 20 °C 3.1: ethanol / 4 h / Reflux 4.1: acetic acid / 4.33 h / Reflux 5.1: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux 6.1: sodium hydroxide / ethanol; water / 2 h / 70 °C View Scheme |
6-nitroisatoic anhydride
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogen / tetrahydrofuran / 2 h / 60 °C / 15001.5 Torr 1.2: 1 h / 20 °C 2.1: ethanol / 4 h / Reflux 3.1: acetic acid / 4.33 h / Reflux 4.1: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux 5.1: sodium hydroxide / ethanol; water / 2 h / 70 °C View Scheme |
N-(2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)acetamide
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethanol / 4 h / Reflux 2: acetic acid / 4.33 h / Reflux 3: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux 4: sodium hydroxide / ethanol; water / 2 h / 70 °C View Scheme |
N-(2-amino-5-acetamidobenzoyl)-o-toluidine
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid / 4.33 h / Reflux 2: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux 3: sodium hydroxide / ethanol; water / 2 h / 70 °C View Scheme |
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Acetoxyacetyl chloride
6-acetoxyacetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 93.8% |
glycolic Acid
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h; Ambient temperature; | 35.2% |
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 93.8 percent / tetrahydrofuran / Ambient temperature 2: 80.9 percent / NaHCO3 / methanol; H2O / 1 h / Heating View Scheme |
The CAS registry number of Afloqualone is 56287-74-2. In addition, the molecular formula is C16H14FN3O and the molecular weight is 283.30. Its IUPAC name is 6-amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4-one. What's more, it is an analogue of methaqualone. It has sedative and muscle relaxant effects, and has had some clinical use.
Physical properties about Afloqualone are: (1)ACD/LogP: 0.85; (2)ACD/LogD (pH 5.5): 0.851; (3)ACD/LogD (pH 7.4): 0.852; (4)ACD/BCF (pH 5.5): 2.61; (5)ACD/BCF (pH 7.4): 2.614; (6)ACD/KOC (pH 5.5): 69.142; (7)ACD/KOC (pH 7.4): 69.233; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 58.69 Å2; (12)Index of Refraction: 1.642; (13)Molar Refractivity: 78.098 cm3; (14)Molar Volume: 216.248 cm3; (15)Polarizability: 30.96 ×10-24cm3; (16)Surface Tension: 47.295 dyne/cm; (17)Density: 1.31 g/cm3; (18)Flash Point: 251.68 °C; (19)Enthalpy of Vaporization: 75.949 kJ/mol; (20)Boiling Point: 492.541 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccccc1n2c(nc3ccc(cc3c2=O)N)CF
(2)Std. InChI: InChI=1S/C16H14FN3O/c1-10-4-2-3-5-14(10)20-15(9-17)19-13-7-6-11(18)8-12(13)16(20)21/h2-8H,9,18H2,1H3
(3)Std. InChIKey: VDOSWXIDETXFET-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 272mg/kg (272mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |
mouse | LD50 | oral | 397mg/kg (397mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |
mouse | LD50 | subcutaneous | 591mg/kg (591mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |
rat | LD50 | intraperitoneal | 385mg/kg (385mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |
rat | LD50 | oral | 249mg/kg (249mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |
rat | LD50 | subcutaneous | 823mg/kg (823mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983. |