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153559-45-6

153559-45-6

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  • Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate Manufacturer/High quality/Best price/In stock

    Cas No: 153559-45-6

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  • High quality Bexarotene Intermediate3,Benzoic Acid, 4-[(5,6,7,8-Tetrahydro-3,5,5,8,8-Pentamethyl-2-Naphthalenyl)Carbonyl]-, Methyl Ester supplier in China

    Cas No: 153559-45-6

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153559-45-6 Usage

Chemical Properties

Off-White Solid

Uses

A possible drug candidate in the treatment of cancers. Intermediate in the preparation of tetramethylcyclohexane derivatives as retinoid X receptors modulators.

Check Digit Verification of cas no

The CAS Registry Mumber 153559-45-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,3,5,5 and 9 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 153559-45:
(8*1)+(7*5)+(6*3)+(5*5)+(4*5)+(3*9)+(2*4)+(1*5)=146
146 % 10 = 6
So 153559-45-6 is a valid CAS Registry Number.
InChI:InChI=1/C24H28O3/c1-15-13-19-20(24(4,5)12-11-23(19,2)3)14-18(15)21(25)16-7-9-17(10-8-16)22(26)27-6/h7-10,13-14H,11-12H2,1-6H3

153559-45-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carbonyl)benzoate

1.2 Other means of identification

Product number -
Other names QC-1728

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:153559-45-6 SDS

153559-45-6Synthetic route

Monomethyl terephthalate
1679-64-7

Monomethyl terephthalate

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
6683-48-3

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
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

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

4-Methoxycarbonylbenzoyl chloride
7377-26-6

4-Methoxycarbonylbenzoyl chloride

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
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%
2,5-dimethyl-2,5-hexanediol
110-03-2

2,5-dimethyl-2,5-hexanediol

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HCl conc. / 3 h / 20 °C
2: 99 percent / AlCl3 / CH2Cl2 / 20 °C
3: 81 percent / FeCl3 / 1,2-dichloro-ethane / 16 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: 56 percent / HCl gas / ethanol
2: 91 percent / AlCl3 / CH2Cl2 / 1.) RT, 30 min, 2.) reflux, 15 min
3: 72 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water
2: aluminum (III) chloride
3: aluminum (III) chloride
View Scheme
2,5-dichloro-2,5-dimethyl hexane
6223-78-5

2,5-dichloro-2,5-dimethyl hexane

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / AlCl3 / CH2Cl2 / 20 °C
2: 81 percent / FeCl3 / 1,2-dichloro-ethane / 16 h / 75 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride
2: aluminum (III) chloride
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / 1 h / 0 - 20 °C
2: iron(III) chloride / 1,2-dichloro-ethane / 75 °C / Inert atmosphere
View Scheme
1,1,4,4,7-pentamethyl-2-oxo-1,2,3,4-tetrahydronaphthalene
29020-85-7

1,1,4,4,7-pentamethyl-2-oxo-1,2,3,4-tetrahydronaphthalene

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
2,2,5,5-tetramethyltetrahydro-3-oxofuran
5455-94-7

2,2,5,5-tetramethyltetrahydro-3-oxofuran

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
toluene
108-88-3

toluene

(+-)-o-toluenesulfinic acid-chloride

(+-)-o-toluenesulfinic acid-chloride

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene
167958-79-4

1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h
2: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
1,1,4,4,7-pentamethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene
167958-78-3

1,1,4,4,7-pentamethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / POCl3, pyridine / 100 °C
2: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h
3: 67 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
2,5-dichloro-2,5-dimethyl hexane
6223-78-5

2,5-dichloro-2,5-dimethyl hexane

petroleum ether

petroleum ether

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / AlCl3 / CH2Cl2 / 1.) RT, 30 min, 2.) reflux, 15 min
2: 72 percent / AlCl3 / CH2Cl2 / 0.25 h / Heating
View Scheme
Monomethyl terephthalate
1679-64-7

Monomethyl terephthalate

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
6683-48-3

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

A

C38H46O2
1349659-51-3

C38H46O2

B

4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid
153559-46-7

4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid

C

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Stage #1: Monomethyl terephthalate; 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With aluminum (III) chloride In dichloromethane at -10 - 44℃; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride; water In dichloromethane; water at 15 - 20℃;
toluene
108-88-3

toluene

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminum (III) chloride / 1 h / 0 - 20 °C
2: iron(III) chloride / 1,2-dichloro-ethane / 75 °C / Inert atmosphere
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid
153559-46-7

4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Heating;100%
With potassium hydroxide In methanol; water at 60℃; for 1h;89%
Stage #1: methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate With water; potassium hydroxide In methanol for 1h; Reflux;
Stage #2: With hydrogenchloride In methanol; water at 20℃;		88%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate
153559-48-9

methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at -30 - 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate In tetrahydrofuran at -30 - 0℃; for 1h;		69%
Stage #1: Methyltriphenylphosphonium bromide With sodium amide In tetrahydrofuran Inert atmosphere;
Stage #2: methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate In tetrahydrofuran for 1h; Wittig reaction; Inert atmosphere;		66%
With sodium amide In tetrahydrofuran Wittig Reaction;66%
cyclopropyltriphenylphosphonium bromide
14114-05-7

cyclopropyltriphenylphosphonium bromide

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

4-[cyclopropylidene-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methyl]-benzoic acid methyl ester

4-[cyclopropylidene-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methyl]-benzoic acid methyl ester

Conditions
ConditionsYield
With Tris(3,6-dioxaheptyl)amine; potassium hexamethylsilazane In toluene Substitution; Heating;69%
dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-<1-methyl-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl>benzoate

methyl 4-<1-methyl-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl>benzoate

Conditions
ConditionsYield
With titanium tetrachloride 1.) CH2Cl2, -30 deg C, 30 min, 2.) CH2Cl2, 30 min; Yield given. Multistep reaction;
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid oxime

cis-4-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl>benzoic acid oxime

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / aq. NaOH / methanol / 2 h / Heating
2: 1.98 g / aq. NH2OH / acetic acid / 1 h / Heating
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

4-[[(E)-Hydroxyimino]-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methyl]-benzoic acid

4-[[(E)-Hydroxyimino]-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methyl]-benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / aq. NaOH / methanol / 2 h / Heating
2: aq. NH2OH / acetic acid / 1 h / Heating
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

SR11173

SR11173

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / KN(SiMe3)2; (MeOCH2CH2OCH2CH2)3N / toluene / Heating
2: 83 percent / aq. KOH; aq. citric acid / ethanol
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

bexarotene
153559-49-0

bexarotene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) 0.5 M potassium bis(trimethylsilyl)amide / 1.) C6H6, tluene, RT, 5 min, 2.) C6H6, toluene, RT, 3 h
2: 91 percent / KOH / methanol; H2O / 1 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaNH2 / 1.) THF, 1 h, 2.) THF, 30 min
2: 85 percent / aq. 5N KOH / methanol / 0.17 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaNH2 / 1.) THF, 15 h, 2.) THF, below 50 deg C, 30 min
2: 93 percent / 5 N aq. KOH / methanol / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hexamethylsilazane / toluene / 0.75 h / 25 - 50 °C / Inert atmosphere
1.2: 2 h / 0 - 5 °C / Inert atmosphere
2.1: potassium hydroxide; water / methanol / 8 h / 25 °C / Reflux
2.2: 10 - 25 °C / pH 1 - 2
View Scheme
Multi-step reaction with 2 steps
1: sodium amide / tetrahydrofuran
2: potassium hydroxide; methanol
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

4-[1-methyl-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]benzoic acid

4-[1-methyl-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) TiCl4 / 1.) CH2Cl2, -30 deg C, 30 min, 2.) CH2Cl2, 30 min
2: 73 percent / 5N aq. KOH / methanol / Heating
View Scheme
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

A

C25H30O
1349659-53-5

C25H30O

B

C26H32
1349659-55-7

C26H32

C

C39H48O
1349659-56-8

C39H48O

D

C40H50
1349659-57-9

C40H50

E

methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate
153559-48-9

methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In toluene at 25 - 50℃; for 0.75h; Inert atmosphere;
Stage #2: methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate In toluene at 0 - 5℃; for 2h; Inert atmosphere;
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

4-(1-(3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid

4-(1-(3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 80 °C
2.1: dimethyl sulfoxide / 2 h / 100 °C
3.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 20 °C
4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -30 - 0 °C
4.2: 3 h / -30 - 0 °C
5.1: lithium hydroxide; water / tetrahydrofuran / 8 h / 50 °C
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-[[3-(dibromomethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]benzoate

methyl 4-[[3-(dibromomethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]benzoate

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃;
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-[(3-formyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]benzoate

methyl 4-[(3-formyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 80 °C
2: dimethyl sulfoxide / 2 h / 100 °C
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-[[3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]benzoate

methyl 4-[[3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 80 °C
2: dimethyl sulfoxide / 2 h / 100 °C
3: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 20 °C
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-[1-[3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethenyl]benzoate

methyl 4-[1-[3-(difluoromethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethenyl]benzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 80 °C
2.1: dimethyl sulfoxide / 2 h / 100 °C
3.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 20 °C
4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -30 - 0 °C
4.2: 3 h / -30 - 0 °C
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

methyl 4-<1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl>benzoate

methyl 4-<1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl>benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -30 - 0 °C / Inert atmosphere
1.2: 1 h / -30 - 0 °C
2.1: diethylzinc; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C
View Scheme
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
153559-45-6

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate

LGD1268

LGD1268

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -30 - 0 °C / Inert atmosphere
1.2: 1 h / -30 - 0 °C
2.1: diethylzinc; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C
3.1: lithium hydroxide; water / tetrahydrofuran / 24 h / 20 °C
View Scheme

153559-45-6Relevant articles and documents

BEXAROTENE DERIVATIVES AND THEIR USE IN TREATING CANCER

-

, (2019/09/18)

This disclosure relates to compositions and methods for treating cancer. Specifically, this disclosure relates to bexarotene derivatives, methods for treating cancer, autoimmune disorders, and/or skin dermatitis, and/or methods for increasing peripheral blood counts and/or improving immune system function.

PROCESS FOR THE PREPARATION OF HIGHLY PURE BEXAROTENE

-

Page/Page column 18-19, (2011/12/02)

The present invention provides an improved process for the preparation of highly pure bexarotene of formula (I). The present invention also provides impurities of bexarotene, method of isolation and identification of these impurities, and use of these impurities as reference marker as well as reference standard.

Modeling, synthesis and biological evaluation of potential Retinoid X Receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene)

Wagner, Carl E.,Jurutka, Peter W.,Marshall, Pamela A.,Groy, Thomas L.,Van Der Vaart, Arjan,Ziller, Joseph W.,Furmick, Julie K.,Graeber, Mark E.,Matro, Erik,Miguel, Belinda V.,Tran, Ivy T.,Kwon, Jungeun,Tedeschi, Jamie N.,Moosavi, Shahram,Danishyar, Amina,Philp, Joshua S.,Khamees, Reina O.,Jackson, Jevon N.,Grupe, Darci K.,Badshah, Syed L.,Hart, Justin W.

experimental part, p. 5950 - 5966 (2010/02/28)

This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use can cause side effects such as hypothyroidism and increased triglyceride concentrations, presumably by disruption of RXR heterodimerization with other nuclear receptors. The novel analogues in the present study have been evaluated forRXR activation in an RXR mammalian-2-hybrid assay as well as an RXRE-mediated transcriptional assay and for their ability to induce apoptosis as well as for their mutagenicity and cytotoxicity. Analysis of 11 novel compounds revealed the discovery of three analogues that best induce RXR-mediated transcriptional activity, stimulate apoptosis, have comparable Ki and EC50 values to 1, and are selective RXR agonists. Our experimental approach suggests that rational drug design can develop new rexinoids with improved biological properties. 2009 American Chemical Society.

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