4133-34-0

Basic information

• Product Name: 7-Methoxy-2-tetralone
• Synonyms: 7-METHOXY-3,4-DIHYDRONAPHTHALEN-2(1H)-ONE;7-METHOXY-2-TETRALONE;3,4-DIHYDRO-7-METHOXY-2(1H)-NAPHTHALENONE;2(1H)-NAPHTHALENONE, 3,4-DIHYDRO-7-METHOXY-;7-methoxy-1,2,3,4-tetrahydronaphthalen-2-one;7-Methoxy-2-Tetralone(7-OHO);7-Methoxyl-2-Tetralone;7-Methoxy-3,4-dihydronaphthalen-2(1H)-one 97%
• CAS NO: 4133-34-0
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• EINECS: 223-954-1
• Product Categories: Benzocycles;Aromatic Ketones (substituted);API intermediates;Fused Ring Systems;C11 to C12;Carbonyl Compounds;Ketones;Building Blocks;C11 to C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 4133-34-0.mol
• Article Data: 20

Chemical Properties

• Melting Point: 23-24 °C
• Boiling Point: 124-126 °C1.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to orange/Liquid After Melting
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000754mmHg at 25°C
• Refractive Index: n20/D 1.566(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: 1.151g/L at 25℃
• BRN: 1953198
• CAS DataBase Reference: 7-Methoxy-2-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-2-tetralone(4133-34-0)
• EPA Substance Registry System: 7-Methoxy-2-tetralone(4133-34-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 4133-34-0(Hazardous Substances Data)

Usage

Uses

7-Methoxy-2-tetralone was used in the synthesis of 2-bromo-3,4-dihydro-7-methoxy-1-naphthaldehyde and 2-substituted octahydrobenzo[f]quinolines.

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

• 123-11-5 4-methoxy-benzaldehyde 
• 73780-78-6 1-(but-3-yn-1-yl)-4-methoxybenzene 
• 1190847-93-8 C₁₅H₂₄O₄ 
• 1160858-16-1 C₁₃H₁₆O₅ 
• 1048330-08-0 7-methoxy-3,4-dihydronaphthalen-2(1H)-one sodium hydrogencarbonate 
• 60-29-7 diethyl ether 
• 3469-26-9 2,7-Dimethoxynaphthalene 
• 63320-02-5 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 60683-71-8 1,4-dihydro-2,7-dimethoxynaphthalene 
• 158365-53-8 7-methoxy-3,4-dihydronaphthalene-1-carbonitrile 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 153993-00-1 tert-Butyl-[3-(4-methoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 90266-06-1 6-Methoxy-3,8a-dihydroazulen-1(2H)-one 

Downstream Products

• 214401-43-1 [7-(4-Cyano-benzyloxy)-naphthalen-2-yl]-acetic acid ethyl ester 
• 214401-46-4 ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate 
• 214401-42-0 [7-(4-Cyano-benzyloxy)-1,2,3,4-tetrahydro-naphthalen-2-yl]-acetic acid ethyl ester 
• 35485-63-3 3',4'-dihydro-7'-methoxyspiro-2,5-dione 
• 134697-67-9 1'-benzyl-3,4-dihydro-7-methoxy-2-oxospiro 
• 1865-83-4 7-methoxy-1,1-dimethyl-3,4-dihydronaphthalene-2-(1H)-one 
• 38205-26-4 8-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-phenyl-1-oxa-3,8-diaza-spiro[4.5]decan-2-one 
• 29093-46-7 1-Allyl-3,4-dihydro-7-methoxy-2(1H)-naphthalinon 
• 603124-10-3 C₃₀H₃₁ClFNO₅ 
• 603124-03-4 C₃₁H₃₄ClNO₅ 
• 603123-04-2 C₃₁H₃₃ClFNO₅ 
• 603124-11-4 C₃₀H₃₁ClFNO₅ 
• 603122-43-6 C₂₅H₂₅ClN₂O₃ 
• 603121-98-8 3-[((7S)-7-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-tert-butyloxycarbonylamino}-5,6,7,8-tetrahydro-2-naphthalenyl)oxy]benzoic acid methyl ester 

Relevant articles and documents

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.

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.