6683-48-3

Basic information

• Product Name: 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene
• Synonyms: 1,2,3,4-TETRAHYDRO-1,1,4,4,6-PENTAMETHYLNAPHTHALENE;1,2,3,4-TETRAHYDRO-1,1,4,4,6-PENTAMETHYLNAPHTHYLENE;1,1,4,4,6-PENTAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE;1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphtalene;1,1,4,4,6-Pentamethyl-1,2,3,4-;1,2,3,4-TETRAHYDRO-1,1,4,4,6-PENTAMETHYLNAPHTALENE: TECH.;1,1,4,4,6-Pentamethyltetralin;1,1,4,4,6-Pentamethyl-1,2,3,4-etrahydronaphthalene
• CAS NO: 6683-48-3
• Molecular Formula: C₁₅H₂₂
• Molecular Weight: 202.34
• EINECS: 229-724-7
• Product Categories: Fused Ring Systems;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 6683-48-3.mol
• Article Data: 39

Chemical Properties

• Melting Point: 31
• Boiling Point: 60-64°C 0,2mm
• Flash Point: 112.5 °C
• Appearance: /
• Density: 0.882 g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene(6683-48-3)
• EPA Substance Registry System: 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene(6683-48-3)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 6683-48-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Targretin analog, has been shown to induce apoptosis in certain leukemia cell lines.

InChI:InChI=1/C15H22/c1-11-6-7-12-13(10-11)15(4,5)9-8-14(12,2)3/h6-7,10H,8-9H2,1-5H3

Synthetic route

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) + toluene (108-88-3) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
With aluminium trichloride for 12h; Heating;	99%
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts alkylation;	99%
With aluminium trichloride In dichloromethane Friedel-Crafts alkylation; Heating;	97%

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
With aluminum (III) chloride In toluene for 0.416667h;	97%

1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene (167958-79-4) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 1h;	80%

toluene (108-88-3) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Stage #1: 2,5-dimethyl-2,5-hexanediol With hydrogenchloride In water at 20℃; for 1h; Stage #2: toluene With aluminum (III) chloride In dichloromethane at 20℃; for 3h;	76%

5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene-1-carbaldehyde (127459-66-9) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
With Wilkinson's catalyst In toluene Heating;

2,5-dimethyl-2,5-hexanediol (110-03-2) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl conc. / 3 h / 20 °C 2: 99 percent / AlCl3 / CH2Cl2 / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 56 percent / HCl gas / ethanol 2: 91 percent / AlCl3 / CH2Cl2 / 1.) RT, 30 min, 2.) reflux, 15 min View Scheme
Multi-step reaction with 2 steps 1: conc. HCl, HCl gas / 0.25 h / 0 °C 2: 80.4 percent / AlCl3 / 1 h / 0 °C View Scheme

1,1,4,4,7-pentamethyl-2-oxo-1,2,3,4-tetrahydronaphthalene (29020-85-7) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 79 percent / POCl3, pyridine / 100 °C 3: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme

2,2,5,5-tetramethyltetrahydro-3-oxofuran (5455-94-7) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 45 percent / AlCl3 / 2 h / 0 - 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 79 percent / POCl3, pyridine / 100 °C 4: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme

toluene (108-88-3) + (+-)-o-toluenesulfinic acid-chloride → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 45 percent / AlCl3 / 2 h / 0 - 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 79 percent / POCl3, pyridine / 100 °C 4: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme

1,1,4,4,7-pentamethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene (167958-78-3) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / POCl3, pyridine / 100 °C 2: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme

1,2,3,4-tetrahydro-1,1,4,4,5,7-hexamethylnaphthalene (94374-39-7) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NBS, 2.) 1-methylpyrrolidin-2-one, 3.) PCC / 1.) CCl4, 77 deg C, 45 min, 2.) H2O, 100 h, 1h, 3.) CH2Cl2, 20 deg C, 2 h 2: 3)3> / toluene / Heating View Scheme

m-xylene (108-38-3) + benzene; toluene → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) H2SO4, 2.) Mg, 4.) H2SO4 / 1.) 20 deg C, 3 h, 2.) THF, 75 deg C, 30 min, 3.) THF, reflux, 30 min, 4.) petroleum ether, 5 - 10 deg C, 30 min 2: 1.) NBS, 2.) 1-methylpyrrolidin-2-one, 3.) PCC / 1.) CCl4, 77 deg C, 45 min, 2.) H2O, 100 h, 1h, 3.) CH2Cl2, 20 deg C, 2 h 3: 3)3> / toluene / Heating View Scheme

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) + 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (96042-30-7) → 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3)

Conditions	Yield
With hydrogenchloride; AlCl3 In toluene

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + acetyl chloride (75-36-5) → 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalenyl)ethanone (17610-24-1)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane for 1h; Ambient temperature;	99%
aluminium trichloride In 1,2-dichloro-ethane	99%
With aluminum (III) chloride In dichloromethane for 5h; Inert atmosphere; Reflux;	96%

methyl 5-(chloromethyl)-2-furoate (2144-37-8) + Methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl) methyl]-2-furoate + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-N'-(2,4,6-trimethoxybenzyl)-2-furohydrazide (637012-34-1) + 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid (263854-27-9)

Conditions	Yield
With sodium hydroxide; aluminium trichloride In methanol; dichloromethane; water; ethyl acetate	A 99% B n/a

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + 3-(methoxycarbonyl)benzoyl chloride (3441-03-0) → methyl 3-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl>benzoate

Conditions	Yield
With aluminum (III) chloride Friedel Crafts Acylation;	98%
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;	80%
With aluminum (III) chloride In dichloromethane at 20℃; Friedel Crafts acylation; Reflux;	2.21 g

Monomethyl terephthalate (1679-64-7) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate (153559-45-6)

Conditions	Yield
With aluminum (III) chloride; thionyl chloride In dichloromethane at 20℃; for 4h; Temperature; Solvent; Reflux;	95.3%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + 4-methoxy-benzoyl chloride (100-07-2) → (4-methoxy-phenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanone (544708-96-5)

Conditions	Yield
With aluminum (III) chloride In dichloromethane	95%
With aluminium trichloride Friedel-Crafts acylation;	70%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + phthalic monoacid monomethyl ester chloride (4397-55-1) → methyl 2-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl>benzoate

Conditions	Yield
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;	91%

4-chlorosulfonylbenzoyl chloride (7516-60-1) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzene-1-sulfonyl chloride

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h; Friedel-Crafts Acylation;	86%
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h;	2.3592 g

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + potassium p-carboxybenzenesulfonate (5399-63-3) → 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzene-1-sulfonyl chloride

Conditions	Yield
Stage #1: potassium p-carboxybenzenesulfonate With thionyl chloride; N,N-dimethyl-formamide at 85℃; for 1.66667h; Stage #2: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h;	86%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (119999-22-3)

Conditions	Yield
With aluminium trichloride; bromine In dichloromethane	85%
With bromine In tetrachloromethane for 0.25h; Ambient temperature;	80%
With bromine In chloroform at 20℃; for 0.5h;	60%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + 4-Methoxycarbonylbenzoyl chloride (7377-26-6) → methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate (153559-45-6)

Conditions	Yield
With aluminum (III) chloride Friedel Crafts Acylation;	82%
With iron(III) chloride In 1,2-dichloro-ethane at 75℃; for 16h; Friedel-Crafts acylation;	81%
With aluminium trichloride In dichloromethane for 0.25h; Heating;	72%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxaldehyde (92654-79-0)

Conditions	Yield
With ammonium cerium(IV) nitrate; acetic acid In water at 100℃; for 1h;	78%
With ammonium cerium(IV) nitrate In acetic acid at 20℃; for 1h;	78%
With ammonium cerium (IV) nitrate; acetic acid at 100℃; for 1h;	77%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxaldehyde (92654-79-0) + 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic acid (103031-30-7)

Conditions	Yield
With ammonium cerium(IV) nitrate; acetic acid at 100℃; for 0.25h;	A 78% B 14%
With ammonium cerium(IV) nitrate; acetic acid at 100℃; for 0.25h;	A 78% B 78%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-bromomethane (119435-90-4)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2.5h; Heating / reflux;	72.5%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 1,1,4,4,6-pentamethyl-7-nitro-1,2,3,4-tetrahydronaphthalene (116233-16-0)

Conditions	Yield
With nitric acid; acetic anhydride	72%
With sulfuric acid; nitric acid at 20℃; for 4h;	62.1%
With sulfuric acid; nitric acid at -10℃;	50%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + 4-iodobenzoic acid chloride (1711-02-0) → 2-(4-iodophenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methanone (926038-65-5)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h;	71%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + methyl 2-acetoxy-4-(chlorocarbonyl)benzoate → methyl 2-hydroxy-4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h;	70%

methyl 5-(chloromethyl)-2-furoate (2144-37-8) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-methyl]-2-furoate (263854-26-8)

Conditions	Yield
With aluminium trichloride In dichloromethane Friedel-Crafts alkylation; Heating;	68%
aluminum (III) chloride In dichloromethane for 2h; Heating / reflux;	46%
With aluminum (III) chloride In dichloromethane for 2h; Friedel Crafts Acylation; Heating / reflux;	46%

methyl 2-(chlorocarbonyl)pyrimidine-5-carboxylate (1427690-41-2) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → methyl 2-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]pyrimidine-5-carboxylate (1427690-40-1)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Reflux;	68%
With aluminum (III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel-Crafts Acylation; Reflux;	1.677 g

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic acid (103031-30-7)

Conditions	Yield
With potassium permanganate; sodium hydroxide In water; chlorobenzene at 100℃; for 16h;	63.3%
Stage #1: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With potassium permanganate; sodium hydroxide In pyridine; water at 95℃; for 16h; Stage #2: With hydrogenchloride In pyridine; water at 1℃; pH=1;	57%
With potassium permanganate Alkaline conditions;	57%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + trifluoromethyl 4-fluorobenzene-1-sulfonate → 1,1,4,4-tetramethyl-6-((trifluoromethoxy)methyl)-1,2,3,4-tetrahydronaphthalene

Conditions

Yield

Stage #1: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With 1,10-phenanthroline-5,6-dione; bathophenanthroline; silver trifluoromethanesulfonate; 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); cesium fluoride at 20℃; for 0.0833333h; Glovebox; Sealed tube; Inert atmosphere; Stage #2: trifluoromethyl 4-fluorobenzene-1-sulfonate at 25℃; for 15h; Glovebox; Sealed tube; Inert atmosphere;

59%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethyl-5,7-dinitronaphthalene (92649-05-3)

Conditions	Yield
With sulfuric acid; nitric acid In 1,2-dichloro-ethane at 0℃; for 2h;	57%
With sulfuric acid; nitric acid

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + 6-chlorocarbonyl-nicotinic acid methyl ester (169124-35-0) → methyl 6-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl>nicotinate (153559-92-3)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Reflux;	54%
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature;	50%
With aluminium trichloride In nitromethane; dichloromethane at 15 - 30℃; for 24h; Friedel-Crafts acylation;
With aluminum (III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel-Crafts Acylation; Reflux;	1.3 g

5-carbethoxythiophene-2-carbonyl chloride (156910-44-0) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → ethyl 5-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>thiophene-2-carboxylate (156910-45-1)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane for 16h; Ambient temperature;	50%

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) + benzoyl chloride (98-88-4) → ethyl 5-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>thiophene-2-carboxylate (156910-45-1)

Conditions	Yield
aluminium trichloride In 1,2-dichloro-ethane	50%

4-(1,3,2-dioxaborinan-2-yl)benzoyl chloride (481725-56-8) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → C22H27BO3 (926038-69-9)

Conditions	Yield
With aluminum (III) chloride	47%

Upstream product

• 108-88-3 toluene 
• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 108-38-3 m-xylene 
• 94374-39-7 1,2,3,4-tetrahydro-1,1,4,4,5,7-hexamethylnaphthalene 
• 167958-78-3 1,1,4,4,7-pentamethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 5455-94-7 2,2,5,5-tetramethyltetrahydro-3-oxofuran 
• 29020-85-7 1,1,4,4,7-pentamethyl-2-oxo-1,2,3,4-tetrahydronaphthalene 
• 110-03-2 2,5-dimethyl-2,5-hexanediol 
• 167958-79-4 1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene 
• 127459-66-9 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene-1-carbaldehyde 

Downstream Products

• 119436-52-1 (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methyl-triphenyl-phosphonium bromide 
• 17610-24-1 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalenyl)ethanone 
• 153559-73-0 ethyl 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)nicotinate 
• 1347735-37-8 ethyl 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)nicotinate 
• 544709-01-5 dimethyl-thiocarbamic acid O-{4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl} ester 
• 544708-99-8 dimethyl-thiocarbamic acid O-[4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-phenyl] ester 
• 544708-98-7 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenol 
• 544708-97-6 (4-hydroxy-phenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanone 
• 119999-22-3 2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene 

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Synthetic method of retinoic acid derivative Am580

The invention discloses a synthetic method of retinoic acid derivative Am580, which comprises: stirring a solution of 2, 5-dimethyl hexane-2, 5-diol in concentrated HCl for 30 min, introducing HCl gasinto the system, carrying out a reaction for 3 h, performing stirring until the system becomes a two-phase mixture, performing cooling to a room temperature, performing filtering to obtain a light pink solid, washing the solid with water, performing recrystallizing in methanol, and performing filtering to obtain an intermediate 3 which is a white solid; dissolving 2, 5-dichloro-2, 5-dimethylhexane in an organic solvent, adding AlCl3 into the solution according to a molar ratio of the 2, 5-dichloro-2, 5-dimethylhexane to the AlCl3 of 1: 0.1-1: 0.2, performing heating to 100-120 DEG C, performing stirring for 16 hours, quenching the reaction by using 3M HCl, performing extracting by using normal hexane, and performing distilling under reduced pressure to remove the solvent to obtain a colorless oily matter intermediate 4. The method has the beneficial effects that the yield of each step is relatively high, the post-treatment is simple, and the industrial production is easier; reaction conditions and a solvent system are optimized for the Friedel-Crafts reaction and the oxidation reaction, and industrial production is better facilitated.

Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts

We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.

COMPOUNDS AND METHODS FOR INHIBITING CYP26 ENZYMES

Compounds described herein are inhibitors of retinoic acid inducible P450 (CYP26) enzymes, and are useful for treating diseases that are responsive to retinoids. Certain compounds have retinoid activity, are resistant to CYP26-mediated catabolism, and are used for treating diseases that are responsive to retinoids.