4133-34-0

Usage

Uses

Used in Pharmaceutical Synthesis:
7-Methoxy-2-tetralone is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 7-Methoxy-2-tetralone is used as a building block for the synthesis of complex organic molecules. Its reactivity and functional groups make it a versatile compound for various chemical reactions.
Specific Applications:
7-Methoxy-2-tetralone has been specifically used in the synthesis of 2-bromo-3,4-dihydro-7-methoxy-1-naphthaldehyde and 2-substituted octahydrobenzo[f]quinolines. These compounds have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H12O2/c1-13-11-5-3-8-2-4-10(12)6-9(8)7-11/h3,5,7H,2,4,6H2,1H3

Synthetic route

(1S,2R)-7-Methoxy-1,2,3,4-tetrahydro-naphthalene-1,2-diol (75804-69-2) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 0.25h; Heating;	98%

1-(but-3-yn-1-yl)-4-methoxybenzene (73780-78-6) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With 2,6-dichloropyridine N-oxide; C33H54AuClP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 6h;	98%

7-methoxy-3,4-dihydronaphthalen-2(1H)-one sodium hydrogencarbonate (1048330-08-0) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With hydrogenchloride In water; toluene at 20℃; for 3h;	92%

C15H24O4 (1190847-93-8) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0 - 20℃; for 2h; Friedel Crafts reaction;	85%

6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (63320-02-5) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With zinc(II) iodide In benzene for 3h; Heating;	74%
With zinc(II) iodide In benzene

C13H16O5 (1160858-16-1) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78 - 20℃; for 4h;	73%

tert-Butyl-[3-(4-methoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane (153993-00-1) → 4-(4-methoxyphenyl)-2-butanone (104-20-1) + 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With naphthalene-1,4-dicarbonitrile In water; acetonitrile for 3h; Irradiation;	A 10% B 72%
With naphthalene-1,4-dicarbonitrile In water; acetonitrile for 4h; Cyclization; desilylation; Irradiation;	A 10% B 72%

6-Methoxy-2,3-dihydro-1aH-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid amide → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With hydrogenchloride Heating;	70%

2,7-Dimethoxynaphthalene (3469-26-9) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With ethanol; sodium und anschlissend mit wss.HCl;
With hydrogenchloride; ammonia; sodium 1) EtOH, Et2O, THF, -78 deg C; Yield given. Multistep reaction;
With hydrogenchloride; ethanol; sodium 1.) reflux, 1 h, 2.) EtOH, reflux, 30 min; Multistep reaction;

1,4-dihydro-2,7-dimethoxynaphthalene (60683-71-8) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride In acetone for 0.5h; Heating;	8.2 g
With hydrogenchloride In water; acetone at 25 - 30℃; for 0.25h;	0.42 g

3,8a-dihydro-6-methoxy-1(2H)-azulenone (90266-06-1) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.5h; Ambient temperature; Yield given;
With trifluoroacetic acid Yield given;

2,7-Dihydroxynaphthalene (582-17-2) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / sodium hydroxide 2: sodium; liquid ammonia / ethanol 3: 8.2 g / hydrochloric acid / acetone / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 2N aq. NaOH / 1.) 55 deg C, 2 h, 2.) reflux 2 h 2: 1.) Na, EtOH, 2.) 2N aq. HCl / 1.) reflux, 1 h, 2.) EtOH, reflux, 30 min View Scheme

4-(4-methoxyphenyl)-2-butanone (104-20-1) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran / 0.33 h / -78 °C 1.2: tetrahydrofuran / 3 h / -78 - 20 °C 2.1: 72 percent / 1,4-dicyanonaphthalene / acetonitrile; H2O / 4 h / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 98 percent / LDA / tetrahydrofuran / 3 h / -78 °C 2: 72 percent / 1,4-dicyanonaphthalene / acetonitrile; H2O / 3 h / Irradiation View Scheme

4-methoxy-benzaldehyde (123-11-5) + solid phase-bound -CH2OC(O)NH2 → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aq. NaOH 2.1: 90 percent / H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr 3.1: LDA / tetrahydrofuran / 0.33 h / -78 °C 3.2: tetrahydrofuran / 3 h / -78 - 20 °C 4.1: 72 percent / 1,4-dicyanonaphthalene / acetonitrile; H2O / 4 h / Irradiation View Scheme

4-(4-methoxyphenyl)-3-buten-2-one (3815-30-3) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 90 percent / H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr 2.1: LDA / tetrahydrofuran / 0.33 h / -78 °C 2.2: tetrahydrofuran / 3 h / -78 - 20 °C 3.1: 72 percent / 1,4-dicyanonaphthalene / acetonitrile; H2O / 4 h / Irradiation View Scheme

7-methoxy-3,4-dihydronaphthalene (60573-58-2) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 10percent aq. NaHCO3, 3-chloroperbenzoic acid / toluene / 2 h / Ambient temperature 2: 74 percent / ZnI2 / benzene / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: m-chloroperoxybenzoic acid 2: ZnI2 / benzene View Scheme
Multi-step reaction with 2 steps 1: 77 percent / N-methylmorpholine N-oxide, osmium tetroxide / H2O; acetone; 2-methyl-propan-2-ol; CCl4 2: 98 percent / p-toluenesulfonic acid / benzene / 0.25 h / Heating View Scheme

7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridinium p-toluenesulfonate / toluene / 3 h / Heating 2: 95 percent / 10percent aq. NaHCO3, 3-chloroperbenzoic acid / toluene / 2 h / Ambient temperature 3: 74 percent / ZnI2 / benzene / 3 h / Heating View Scheme

7-Methoxy-1-tetralone (6836-19-7) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 51.1 g / NaBH4 / methanol; tetrahydrofuran / 2 h / Ambient temperature 2: pyridinium p-toluenesulfonate / toluene / 3 h / Heating 3: 95 percent / 10percent aq. NaHCO3, 3-chloroperbenzoic acid / toluene / 2 h / Ambient temperature 4: 74 percent / ZnI2 / benzene / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 1.) ZnI2; 2.) POCl3 / 2.) pyridine 2: 80 percent / n-Bu4NHSO4, NaOH, H2O2 3: 70 percent / 3N HCl / Heating View Scheme
Multi-step reaction with 3 steps 1: 1) NaBH4, 2) p-TsOH / 2) benzene 2: m-chloroperoxybenzoic acid 3: ZnI2 / benzene View Scheme
Multi-step reaction with 3 steps 1: 1.) sodium borohydride, ethanol, 15 min., reflux 2.) p-toluenesulfonic acid, benzene, reflux 2: 77 percent / N-methylmorpholine N-oxide, osmium tetroxide / H2O; acetone; 2-methyl-propan-2-ol; CCl4 3: 98 percent / p-toluenesulfonic acid / benzene / 0.25 h / Heating View Scheme

7-methoxy-3,4-dihydronaphthalene-1-carbonitrile (158365-53-8) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / n-Bu4NHSO4, NaOH, H2O2 2: 70 percent / 3N HCl / Heating View Scheme

diethyl ether (60-29-7) + 2,7-Dimethoxynaphthalene (3469-26-9) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
With hydrogenchloride In methanol; water; sodium carbonate

4-methoxy-benzaldehyde (123-11-5) → 7-methoxyl-2-tetralone (4133-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aluminium; mercury(I) chloride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: 2,6-dichloropyridine N-oxide; C33H54AuClP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / 1,2-dichloro-ethane / 6 h / 50 °C View Scheme

7-methoxyl-2-tetralone (4133-34-0) + carbonic acid dimethyl ester (616-38-6) → methyl 7-methoxy-2-oxotetralin-1-carboxylate (34865-33-3)

Conditions	Yield
With sodium hydride In benzene for 2h; Heating;	100%

7-methoxyl-2-tetralone (4133-34-0) + benzylamine (100-46-9) → N-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (83343-23-1)

Conditions	Yield
Stage #1: 7-methoxyl-2-tetralone; benzylamine In dichloromethane for 0.25h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 15h; Inert atmosphere;	100%
Stage #1: 7-methoxyl-2-tetralone; benzylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 15h; Inert atmosphere;	100%
Stage #1: 7-methoxyl-2-tetralone; benzylamine With acetic acid In methanol at 20℃; for 0.5h; Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃;	97%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;

acetamide (60-35-5) + 7-methoxyl-2-tetralone (4133-34-0) → N-(7-methoxy-3,4-dihydronaphthalen-2-yl)acetamide

Conditions	Yield
With toluene-4-sulfonic acid In toluene Inert atmosphere; Reflux;	98%
With toluene-4-sulfonic acid In toluene for 20h; Inert atmosphere; Reflux; Dean-Stark;	75%
With toluene-4-sulfonic acid In water; toluene Inert atmosphere;
With toluene-4-sulfonic acid In toluene for 20h; Inert atmosphere; Dean-Stark; Reflux;
With toluene-4-sulfonic acid In toluene for 20h; Reflux; Dean-Stark; Inert atmosphere;

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 7-methoxyl-2-tetralone (4133-34-0) → ethyl 2-(7-methoxy-3,4-dihydronaphthalen-2(1H)-ylidene)acetate

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In 1,2-dimethoxyethane; mineral oil at 20℃; for 1h; Stage #2: 7-methoxyl-2-tetralone In 1,2-dimethoxyethane; mineral oil at 20℃; for 3h;	97%

7-methoxyl-2-tetralone (4133-34-0) → (R)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

Conditions	Yield
With isopropyl alcohol; NADH; magnesium chloride In methanol at 30℃; for 1h; pH=8; aq. buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	97%
With formic acid; (S)-chloro[(1,2,3,4,5-η)-pentamethyl-2,4-cyclopentadien-1-yl](2-pyrrolidinecarboxamidato-kN1,kN2)iridium (III); triethylamine In methanol at -10℃; for 48h;	480 mg
With dichloro(benzene)ruthenium(II) dimer; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine Noyori Asymmetric Hydrogenation;

7-methoxyl-2-tetralone (4133-34-0) + carbonic acid dimethyl ester (616-38-6) → 2-hydroxy-7-methoxy-3,4-dihydronaphthalene-1-carboxylic acid methyl ester (63491-51-0)

Conditions	Yield
Stage #1: 7-methoxyl-2-tetralone With sodium hydride In benzene for 0.5h; Reflux; Stage #2: carbonic acid dimethyl ester In benzene for 3h; Reflux;	96%
Stage #1: 7-methoxyl-2-tetralone; carbonic acid dimethyl ester With sodium hydride Reflux; Inert atmosphere; Stage #2: With water; ammonium chloride	91%

7-methoxyl-2-tetralone (4133-34-0) + thiourea (17356-08-0) → 8-methoxynaphtho[2,1-d]thiazol-2-amine

Conditions	Yield
With iodine; oxygen; toluene-4-sulfonic acid In dimethyl sulfoxide at 75℃; under 760.051 Torr; for 24h;	95%

7-methoxyl-2-tetralone (4133-34-0) + benzyl bromide (100-39-0) → 1-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one (263714-29-0)

Conditions	Yield
Stage #1: 7-methoxyl-2-tetralone With pyrrolidine In methanol for 2h; Stage #2: benzyl bromide In acetonitrile at -5 - 20℃;	95%
Stage #1: 7-methoxyl-2-tetralone With pyrrolidine In methanol at 20℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In acetonitrile at 20℃; Inert atmosphere; Stage #3: With acetic acid In methanol; dichloromethane; water

7-methoxyl-2-tetralone (4133-34-0) + methyl iodide (74-88-4) → 7-methoxy-1,1-dimethyl-3,4-dihydronaphthalene-2-(1H)-one (1865-83-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	93%
With tetrabutylammonium sulfate; potassium hydroxide In tetrahydrofuran; water at 20℃; for 2h;	91%
Stage #1: 7-methoxyl-2-tetralone With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 0℃; for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; tert-butyl alcohol at 20℃; for 2h; Inert atmosphere;	79%

2-(4-phenyl-piperazin-1-yl)-ethylamine (21091-61-2) + 7-methoxyl-2-tetralone (4133-34-0) → (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-[2-(4-phenyl-piperazin-1-yl)-ethyl]-amine (744209-08-3, 744209-09-4, 444145-80-6)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;	93%
Stage #1: 2-(4-phenyl-piperazin-1-yl)-ethylamine; 7-methoxyl-2-tetralone With acetic acid In 1,2-dichloro-ethane at 20℃; for 0.333333h; Stage #2: With sodium cyanoborohydride In methanol; 1,2-dichloro-ethane at 20℃; for 12h; Further stages.;	69.44%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane

7-methoxyl-2-tetralone (4133-34-0) → 1,2,3,4-tetrahydro-7-methoxy-naphthalen-2-ol (13511-60-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at -20 - 20℃; for 4h; Inert atmosphere;	93%
With sodium tetrahydroborate; ethanol at 20℃; Cooling with ice;	93%
With sodium tetrahydroborate In ethanol at 20℃; for 4h;

7-methoxyl-2-tetralone (4133-34-0) + 3-nitro-benzaldehyde (99-61-6) + malononitrile (109-77-3) → 3-amino-9-methoxy-1-(3-nitrophenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With aluminum oxide; potassium fluoride In ethanol for 2h; Heating;	92%

7-methoxyl-2-tetralone (4133-34-0) + 4-bromo-benzaldehyde (1122-91-4) + malononitrile (109-77-3) → 3-amino-1-(4-bromo-phenyl)-9-methoxy-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With aluminum oxide; potassium fluoride In ethanol for 3h; Heating;	92%

4-fluorobenzylidenemalononitrile (2826-22-4) + 7-methoxyl-2-tetralone (4133-34-0) → 3-amino-9-methoxy-1-(4-fluorophenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 17h;	92%

7-methoxyl-2-tetralone (4133-34-0) + 3-nitrobenzylidenemalononitrile (2826-32-6) → 3-amino-9-methoxy-1-(3-nitrophenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	92%

o-chlorobenzylidene malononitrile (2698-41-1) + 7-methoxyl-2-tetralone (4133-34-0) → 3-amino-1-(2-chlorophenyl)-9-methoxy-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	91%

Pyruvic aldehyde dimethyl acetal (6342-56-9) + 7-methoxyl-2-tetralone (4133-34-0) → 7-methoxy-3-methylnaphtho[2,3-b]furan

Conditions	Yield
Stage #1: 7-methoxyl-2-tetralone With tributyl-amine; titanium tetrachloride In dichloromethane at -35℃; Stage #2: Pyruvic aldehyde dimethyl acetal In dichloromethane at -35 - 20℃;	91%

7-methoxyl-2-tetralone (4133-34-0) + 2-(3-chlorobenzylidene)malononitrile (2972-73-8) → 3-amino-9-methoxy-1-(3-chlorophenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 19h;	90%

7-methoxyl-2-tetralone (4133-34-0) + 2-(2-nitrobenzylidene)malononitrile (2826-30-4) → 3-amino-9-methoxy-1-(2-nitrophenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	89%

7-methoxyl-2-tetralone (4133-34-0) + 2-(2,4-dichlorobenzylidene)malononitrile (2972-76-1) → 3-amino-1-(2,4-dichlorophenyl)-9-methoxy-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 18h;	89%

piperonal (120-57-0) + 7-methoxyl-2-tetralone (4133-34-0) + malononitrile (109-77-3) → 3-amino-9-methoxy-1-(3,4-methylenedioxyphenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With aluminum oxide; potassium fluoride In ethanol for 5h; Heating;	88%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 7-methoxyl-2-tetralone (4133-34-0) → (7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester (108972-18-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; water	88%

2-benzo[1,3]dioxol-5-ylmethylene-malononitrile (2972-82-9) + 7-methoxyl-2-tetralone (4133-34-0) → 3-amino-9-methoxy-1-(3,4-methylenedioxyphenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	87%

7-methoxyl-2-tetralone (4133-34-0) + 3,4-dichlorobenzaldehyde (6287-38-3) + malononitrile (109-77-3) → 3-amino-1-(3,4-dichloro-phenyl)-9-methoxy-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With aluminum oxide; potassium fluoride In ethanol for 2.5h; Heating;	86%

2-(4-methoxyphenylmethylene)malononitrile (2826-26-8) + 7-methoxyl-2-tetralone (4133-34-0) → 3-amino-9-methoxy-1-(4-methoxyphenyl)-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	86%

7-methoxyl-2-tetralone (4133-34-0) + 3,4-dimethoxybenzylidenemalononitrile (2972-80-7) → 3-amino-1-(3,4-dimethoxyphenyl)-9-methoxy-5,6-dihydro-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 40 - 50℃; for 20h;	86%

7-methoxyl-2-tetralone (4133-34-0) + 1-chloro-2,2-dimethylcyclopropyl p-tolyl sulfoxide (1060767-14-7) → C16H20O2 (1329042-08-1)

Conditions	Yield
Stage #1: 1-chloro-2,2-dimethylcyclopropyl p-tolyl sulfoxide With isopropylmagnesium chloride In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 7-methoxyl-2-tetralone With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;	86%

Upstream product

• 3469-26-9 2,7-Dimethoxynaphthalene 
• 60683-71-8 1,4-dihydro-2,7-dimethoxynaphthalene 
• 90266-06-1 6-Methoxy-3,8a-dihydroazulen-1(2H)-one 
• 75804-69-2 (1S,2R)-7-Methoxy-1,2,3,4-tetrahydro-naphthalene-1,2-diol 
• 63320-02-5 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 153993-00-1 tert-Butyl-[3-(4-methoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 60573-58-2 7-methoxy-3,4-dihydronaphthalene 
• 32820-10-3 7-methoxy-1,2,3,4-tetrahydro-1-naphthol 
• 6836-19-7 7-Methoxy-1-tetralone 
• 158365-53-8 7-methoxy-3,4-dihydronaphthalene-1-carbonitrile 

Downstream Products

• 5060-80-0 7-methoxy-3,4-dihydro-1H-naphthalen-2-one-(2,4-dinitro-phenylhydrazone) 
• 134697-67-9 1'-benzyl-3,4-dihydro-7-methoxy-2-oxospiro 
• 35485-63-3 3',4'-dihydro-7'-methoxyspiro-2,5-dione 
• 23076-74-6 1-Ethyl-7-methoxy-naphthalin 
• 148258-42-8 (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine 
• 744209-03-8 {2-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-ethyl}-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 477788-88-8 {4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 83343-23-1 N-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 
• 121216-42-0 (2S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 
• 231623-76-0 N-[(2S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide 
• 539828-38-1 (1-benzyl-piperidin-4-yl)-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 

Relevant academic research and scientific papers

Synthesis and Bioactivity of a Brasilicardin A Analogue Featuring a Simplified Core

An analogue 2 of Brasilicardin A, 1 (BraA), a potent immunosuppressive and cytotoxic agent, was synthesized in which the natural tricyclic skeleton was replaced with a synthetically more accessible substituted tetrahydronaphthalene core. BraA, this analogue (BraL), and cyclosporine A were tested for their ability to inhibit the proliferation of human T cells upon CD3/CD28 activation. Although BraL did not impact T cell activation over the dose range tested, this study shows the inhibitory activity of BraA on human T cells for the first time.

IMPROVED PROCESS FOR THE PREPARATION OF 9-ETHYL-6,6-DIMETHYL-8-[4-(MORPHOLIN-4-YL) PIPERIDIN-1-YL]-11-OXO-6,11-DIHYDRO-5H-BENZO[B]CARBAZOLE-3-CARBONITRILE HYDROCHLORIDE

The present invention relates to novel process for the preparation of 9-ethyl-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloride compound of formula-1a, represented by the following structural formula: The present invention also provides an improved process for the preparation of tert-butyl-4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoate having the following structural formula which is useful in the preparation of Alectinib and its pharmaceutical acceptable salts.

Gold-Catalyzed Oxidation Terminal Alkyne: An Approach to Synthesize Substituted Dihydronaphthalen-2(1H)-ones and Phenanthrenols

A facile gold-catalyzed oxidation terminal alkynes to synthesize substituted dihydronaphthalen-2(1H)-ones 3 and phenanthrenols 5 was realized. Various useful structures and drug precursors were generated in up to 99% yield under mild condition and low catalyst loading.

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

TiCl4-promoted intramolecular cyclization of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones: an expedient method to prepare 2-tetralones

DABCO is a very effective catalyst in the formation of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones 12 from the corresponding α-carbonatoaldehyde. Intramolecular cyclization of cyclic carbonates 12 promoted by TiCl4 affords 2-tetralones 13 contain

A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal

4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tande

Discovery of a novel series of benzoic acid derivatives as potent and selective human β3 adrenergic receptor agonists with good oral bioavailability. 3. Phenylethanolaminotetraline (PEAT) skeleton containing biphenyl or biphenyl ether moiety

We designed a series of benzoic acid derivatives containing the biphenyl ether or biphenyl template on the RHS and a phenylethanolaminotetraline (PEAT) skeleton, which was prepared by highly stereoselective synthesis, to generate two structurally different lead compounds (10c, 10m) with a good balance of potency, selectivity, and pharmacokinetic profile. Further optimization of the two lead compounds to improve potency led to several potential candidates (i.e., 11f, 11l, 11o, 12b). In particular, biphenyl analogue 12b exhibited an excellent balance of high potency (EC50 = 0.38 nM) for β3, high selectivity over β1 and β2, and good pharmacokinetic properties in rats, dogs, and monkeys.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

A convenient strategy for the total synthesis of pisiferic acid type diterpenes

A practical method for the total synthesis of pisiferic acid type diterpenoids is described. This involves Robinson annulation of the keto ester for the key intermediate.

New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations: Construction of Benzannulated and Benzospiroannulated Compounds

Efficient intramolecular α-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.