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CAS No.: | 65472-88-0 |
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Name: | Naftifine |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C21H21N |
Molecular Weight: | 287.404 |
Synonyms: | 1-Naphthalenemethanamine,N-methyl-N-(3-phenyl-2-propenyl)-, (E)-;1-Naphthalenemethanamine, N-methyl-N-[(2E)-3-phenyl-2-propenyl]-(9CI);Naftifine;Naftifungin; |
Density: | 1.082 g/cm3 |
Melting Point: | 177 °C |
Boiling Point: | 440.1 °C at 760 mmHg |
Flash Point: | 194.4 °C |
Hazard Symbols: | Xn,Xi |
Risk Codes: | R22; R36/37/38 |
PSA: | 3.24000 |
LogP: | 5.78700 |
formaldehyd
(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine
naftifine
Conditions | Yield |
---|---|
With sodium dihydrogen phosphate In 1,4-dioxane; water at 60℃; for 0.166667h; | 100% |
With sodium dihydrogenphosphate In 1,4-dioxane at 60℃; for 0.333333h; | 91% |
With sodium tetrahydroborate 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Pt(COD)Cl2; bis[2-(diphenylphosphino)phenyl] ether In 1,4-dioxane for 12h; Heating; | 98% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 12h; Temperature; Solvent; Inert atmosphere; | 96% |
With 1,10-Phenanthroline; palladium diacetate In toluene at 100℃; for 17h; Inert atmosphere; Schlenk technique; regioselective reaction; | 83% |
Stage #1: N-methyl-1-naphthalenemethylamine; (2E)-3-phenyl-2-propen-1-ol With manganese(IV) oxide; polymer-bound trimethyl ammonium cyanoborohydride In dichloromethane for 5h; Stage #2: With acetic acid for 17h; | 72% |
With triscarbonyl‐(η4–3,4‐bis(4‐methoxyphenyl)‐2,5‐diphenylcyclopenta‐2,4‐dienone)iron In nitromethane; toluene at 130℃; for 24h; Schlenk technique; Inert atmosphere; | 61% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In water at 20℃; for 0.333333h; chemoselective reaction; | 98% |
Conditions | Yield |
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With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 36h; Glovebox; Molecular sieve; Schlenk technique; | 96% |
(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine
acetonitrile
naftifine
Conditions | Yield |
---|---|
With 18-crown-6 ether; carbon dioxide at 80℃; under 750.075 Torr; for 72h; Inert atmosphere; Schlenk technique; Glovebox; | 95% |
(±)-3-(N-methyl-N-((naphthalen-5-yl)methyl)amino)-1-phenylpropan-1-ol
naftifine
Conditions | Yield |
---|---|
With hydrogenchloride In water Reflux; | 90% |
With hydrogenchloride for 2h; Heating; |
1-naphthalene methanol
(E)-N-methylcinnamylamine
naftifine
Conditions | Yield |
---|---|
Stage #1: 1-naphthalene methanol; (E)-N-methylcinnamylamine With manganese(IV) oxide; polymer-bound trimethyl ammonium cyanoborohydride In dichloromethane for 5h; Stage #2: With acetic acid for 17h; | 62% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran; water at 80℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique; | 62% |
formaldehyd
trans-2-phenylvinylboronic acid
N-methyl-1-naphthalenemethylamine
naftifine
Conditions | Yield |
---|---|
Mechanism; multistep reaction; other substrates, other boronic acids; E-selectivity; | |
1) dioxane, 90 deg C, 10 min, 2) dioxane, 90 deg C, 10 min; Yield given. Multistep reaction; |
(naphth-1-yl)methylamine
naftifine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: manganese dioxide; NaBH4; 4A MS / CH2Cl2 / 17 h / Heating 1.2: 86 percent / MeOH / 0.67 h / 0 - 20 °C 2.1: 91 percent / NaH2PO4 / dioxane / 0.33 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: benzene / Heating 2: 100 percent / NaBH4 / methanol / 0.33 h / 40 °C 3: 2.) NaBH4 / 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h View Scheme | |
Multi-step reaction with 3 steps 2: NaBH4 3: 100 percent / NaH2PO3 / H2O; dioxane / 0.17 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: dichloro( 1,5-cyclooctadiene)platinum(ll); bis[2-(diphenylphosphino)phenyl] ether / 1,4-dioxane / 110 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere; Reflux 2.1: [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; diphenylsilane / N,N-dimethyl-formamide / 48 h / 50 °C / 760.05 Torr View Scheme |
The Naftifine, with the CAS registry number 65472-88-0, is also known as N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine. This chemical's molecular formula is C21H21N and molecular weight is 287.40. Its IUPAC name is called (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine. This chemical's classification codes are Anti-Infective Agents; Antifungal agents. Naftifine is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis.
Physical properties of Naftifine: (1)ACD/LogP: 5.80; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.4; (4)ACD/LogD (pH 7.4): 5.11; (5)ACD/BCF (pH 5.5): 60.47; (6)ACD/BCF (pH 7.4): 3087; (7)ACD/KOC (pH 5.5): 136.99; (8)ACD/KOC (pH 7.4): 6993.87; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.655; (13)Molar Refractivity: 97.45 cm3; (14)Molar Volume: 265.4 cm3; (15)Surface Tension: 46 dyne/cm; (16)Density: 1.082 g/cm3; (17)Flash Point: 194.4 °C; (18)Enthalpy of Vaporization: 69.71 kJ/mol; (19)Boiling Point: 440.1 °C at 760 mmHg; (20)Vapour Pressure: 6.07E-08 mmHg at 25°C.
Preparation: this chemical can be prepared by formaldehyde and N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine. This reaction will need reagent NaH2PO3 and solvent H2O, dioxane. The reaction time is 10 min with reaction temperature of 60 ℃. The yield is about 100%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(CC=CC1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
(2)Isomeric SMILES: CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
(3)InChI: InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+
(4)InChIKey: OZGNYLLQHRPOBR-DHZHZOJOSA-N