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CAS No. : | 101827-46-7 | MDL No. : | MFCD00917064 |
Formula : | C23H28ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LJBSAUIFGPSHCN-UHFFFAOYSA-N |
M.W : | 353.93 | Pubchem ID : | 443867 |
Synonyms : |
KP363 Hydrochloride;Butenafine (hydrochloride);KP-363;Butenafine Hydrochloride
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 112.15 |
TPSA : | 3.24 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.45 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 7.06 |
Log Po/w (WLOGP) : | 6.27 |
Log Po/w (MLOGP) : | 5.46 |
Log Po/w (SILICOS-IT) : | 5.78 |
Consensus Log Po/w : | 4.91 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.63 |
Solubility : | 0.0000838 mg/ml ; 0.000000237 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.95 |
Solubility : | 0.0000401 mg/ml ; 0.000000113 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.31 |
Solubility : | 0.00000172 mg/ml ; 0.0000000049 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.91 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium carbonate In <i>N</i>-methyl-acetamide; acetone; benzene | 1 EXAMPLE 1 EXAMPLE 1 A mixture of 1.94 g of 1-chloromethylnaphthalene, 1.77 g of N-methyl-4-tert-butylbenzylamine, 1.17 g of sodium carbonate and 10 ml of dimethylformamide was stirred for 14 hours at 50° C. The reaction mixture was poured into water and extracted with benzene, and the benzene solution was washed with water. After distilling away benzene, 1.5 ml of concentrated hydrochloric acid was added, an excess of concentrated hydrochloric acid was removed under reduced pressure, a small amount of acetone was added and formed white crystal (2.75 g) was filtrated. White plate crystal of N-(4-tert-butylbenzyl)-N-methyl-1-naphthylmethylamine hydrochloride was obtained by recrystallization from acetone/ethanol. Melting point: 211° to 213° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 Production of N-methyl-N-(4'-t-butylbenzyl)-1-naphthylmethylamine hydrochloride EXAMPLE 2 Production of N-methyl-N-(4'-t-butylbenzyl)-1-naphthylmethylamine hydrochloride Hydrochloric acid/ethanol was added to 1.0 g of the compound obtained in Example 1, and the mixture was concentrated. The residue was recrystallized from methanol/acetic acid to give 0.95 g of the desired hydrochloride having a melting point 200° to 202° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water / Inert atmosphere 2: tris(pentafluorophenyl)borate; tetrakis(actonitrile)copper(I) hexafluorophosphate; triphenylmethyl alcohol; 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In water Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.1% | Stage #1: 4-tert-Butylbenzaldehyde; N-methyl-1-naphthalenemethylamine With hydrogen In methanol at 60 - 65℃; for 5h; Stage #2: With hydrogenchloride In methanol; water | 1-9 Example 1 Add N-methyl-1-naphthylmethylamine (17.12g, 0.10mol) and p-tert-butylbenzaldehyde (17.03g, 0.105mol) to methanol (200mL), stir and mix well, add Raney Ni (1.71g) ), the reaction system was passed H2 to 0.3MPa, and the temperature was controlled at 60-65°C for 5 hours. The reaction solution was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to 1/4 volume, and HCl/methanol (150mL, 2mol/L) was added. After salt formation, continue to stir and crystallize for 2 to 3 hours, and then filter. The filter cake is dried under reduced pressure to become butenafol hydrochloride. The yield is 95.1%, HPLC: 99.89%, and the maximum single impurities are less than 0.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.3% | Stage #1: 1-naphthaldehyde; N-(4-tert-butylbenzyl)methylamine With hydrogen; acetic acid In methanol at 60 - 65℃; for 4h; Stage #2: With hydrogenchloride In methanol; water | 1-12 Example 1 N-methyl-4-tert-butylbenzylamine (17.73g, 0.10mol),1-Naphthaldehyde (16.40g, 0.105mol)Add to methanol (200mL),Then add glacial acetic acid (6.00g, 0.10mol),After stirring and mixing, add Raney Ni (1.77g),The reaction system is fed with H2 to 0.3MPa,After reacting at 6065 for 4h,The reaction solution was reduced to room temperature, adjusted to neutral with sodium hydroxide solution, and filtered,The filtrate was extracted with chloroform (100mL×3), and the combined extracts were concentrated to dryness under reduced pressure.Add HCl/methanol (150mL, 2mol/L) to form a salt,Continue to stir and crystallize for 2 to 3 hours and then filter.The filter cake is dried under reduced pressure butenafine hydrochloride,The yield was 96.3%, HPLC: 99.87%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris(triphenylphosphine)ruthenium(II) chloride at 100℃; for 7h; Inert atmosphere; Schlenk technique; Sealed tube; | 1-8 Example 1 Under the protection of argon, RuCl2(PPh3)2(0.14g, 0.2mmol),N-(4-tert-butylbenzyl)-1-naphthylmethylamine (3.03g, 0.01mol), methanol (6mL) are added to the Schlenk device,After sealing, it was placed in a temperature-controlled oil bath at 100°C for 7 hours. After the reaction solution dropped to room temperature,The reaction solution was added to purified water (50mL), stirred for 10min and then extracted with dichloromethane (50mL×3).The combined extracts were concentrated to dryness under reduced pressure, and HCl/methanol (40mL, 2mol/L) was added to form a salt.Continue to stir and crystallize for 2 to 3 hours and then filter. After the filter cake is dried under reduced pressure, it is butenafine hydrochloride., The yield is 95.6%, HPLC: 99.89%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.8% | Stage #1: p-tert-butylbenzyl alcohol; N-methyl-1-naphthalenemethylamine With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In water at 110℃; for 8h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In methanol | 1-12 Example 2 Under the protection of nitrogen,Put [Cp*IrCl2]2 (1.59g, 0.002mol),Sodium bicarbonate (0.42g, 0.005mol),N-methyl-1-naphthylmethylamine (17.12g, 0.10mol),P-tert-butylbenzyl alcohol (18.07g, 0.11mol),Deionized water (150mL) is added to the Schlenk device,Sealed and placed in a temperature-controlled 110 oil bath until reacted for 8 hours,After the reaction, the reaction solution was cooled to room temperature, and dichloromethane (50mL×3) was added for extraction.Combine the extracts and concentrate to dryness under reduced pressure,Add HCl/methanol (300mL, 0.5mol/L) to form a salt,Continue to stir and crystallize for 2 to 3 hours and then filter.After the filter cake is dried under reduced pressure, it is butenafine hydrochloride.The yield was 96.8%, HPLC: 99.80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.1% | Stage #1: 1-naphthalene methanol; N-(4-tert-butylbenzyl)methylamine With potassium; nickel In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 70℃; Inert atmosphere; Dean-Stark; Reflux; Stage #2: With hydrogenchloride In methanol | 1-9 Example 1 Under argon protection, the temperature is controlled at 0-70°C, potassium (9.38g, 0.24mol) is added to the xylene (600mL) solution of 1-naphthalenemethanol (142.38g, 0.90mol), and the argon protection is stopped after stirring. Add N-methyl-p-tert-butylbenzylamine (88.64g, 0.50mol) in xylene (800mL) solution and nickel powder (100 mesh, 2.35g, 0.04mol), then add Dean-Stark device, temperature control reflux After the completion of the reaction, the reaction solution was cooled to room temperature, filtered, and the filtrate was washed with purified water (400mL×3), concentrated under reduced pressure to dryness, added HCl/methanol (800mL, 2mol/L) to form a salt, and continued to stir and crystallize for 2-3h. After filtration, the filter cake was dried under reduced pressure to obtain butenafine hydrochloride, with a yield of 95.1%, and HPLC: 99.91%. |
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