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65472-88-0

Basic Information
CAS No.: 65472-88-0
Name: Naftifine
Article Data: 27
Molecular Structure:
Molecular Structure of 65472-88-0 (Naftifine)
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
Synthetic route
50-00-0

formaldehyd

92610-10-1

(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

65472-88-0

naftifine

Conditions
ConditionsYield
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;
14489-75-9

N-methyl-1-naphthalenemethylamine

4407-36-7

(2E)-3-phenyl-2-propen-1-ol

65472-88-0

naftifine

Conditions
ConditionsYield
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%
16519-25-8

(E)-cinnamyl phenyl ether

14489-75-9

N-methyl-1-naphthalenemethylamine

65472-88-0

naftifine

Conditions
ConditionsYield
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%
140-10-3

(E)-3-phenylacrylic acid

14489-75-9

N-methyl-1-naphthalenemethylamine

65472-88-0

naftifine

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 36h; Glovebox; Molecular sieve; Schlenk technique;96%
92610-10-1

(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

75-05-8

acetonitrile

65472-88-0

naftifine

Conditions
ConditionsYield
With 18-crown-6 ether; carbon dioxide at 80℃; under 750.075 Torr; for 72h; Inert atmosphere; Schlenk technique; Glovebox;95%
98977-94-7

(±)-3-(N-methyl-N-((naphthalen-5-yl)methyl)amino)-1-phenylpropan-1-ol

65472-88-0

naftifine

Conditions
ConditionsYield
With hydrogenchloride In water Reflux;90%
With hydrogenchloride for 2h; Heating;
4780-79-4

1-naphthalene methanol

60960-88-5, 93085-46-2, 83554-67-0

(E)-N-methylcinnamylamine

65472-88-0

naftifine

Conditions
ConditionsYield
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%
108-86-1

bromobenzene

14489-75-9

N-methyl-1-naphthalenemethylamine

1-acetoxy-5-methyl-3,7-dioxo-9-vinyl-2,8-dioxa-5-aza-1-borabicyclo[3.3.1]nonan-5-ium-1-uide

65472-88-0

naftifine

Conditions
ConditionsYield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran; water at 80℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;62%
50-00-0

formaldehyd

6783-05-7

trans-2-phenylvinylboronic acid

14489-75-9

N-methyl-1-naphthalenemethylamine

65472-88-0

naftifine

Conditions
ConditionsYield
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;
118-31-0

(naphth-1-yl)methylamine

65472-88-0

naftifine

Conditions
ConditionsYield
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
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Specification

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