166978-48-9

Basic information

• Product Name: 4,4-Dimethyl-7-ethynyl-1-tetralone
• Synonyms: 4,4-Dimethyl-7-ethynyl-1-tetralone;7-Ethynyl-3,4-dihydro-4,4-diMethyl-1(2H)-naphthalenone;7-ethynyl-3,4-dihydro-4,4-diMethylnaphthalen-1-(2H)-one;7-Ethynyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one
• CAS NO: 166978-48-9
• Molecular Formula: C₁₄H₁₄O
• Molecular Weight: 198.26036
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 166978-48-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 316.7±41.0 °C(Predicted)
• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 4,4-Dimethyl-7-ethynyl-1-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-Dimethyl-7-ethynyl-1-tetralone(166978-48-9)
• EPA Substance Registry System: 4,4-Dimethyl-7-ethynyl-1-tetralone(166978-48-9)

Safety Data

• Hazardous Substances Data: 166978-48-9(Hazardous Substances Data)

Usage

Description

4,4-Dimethyl-7-ethynyl-1-tetralone is an off-white solid that serves as an intermediate in the production of high affinity retinoic acid receptor (RAR) antagonists. It is a synthetic organic compound with a unique molecular structure featuring two methyl groups and an ethynyl group attached to a tetralone core.

Uses

Used in Pharmaceutical Industry:
4,4-Dimethyl-7-ethynyl-1-tetralone is used as an intermediate in the synthesis of high affinity retinoic acid receptor (RAR) antagonists for the pharmaceutical industry. These RAR antagonists are important in the development of drugs targeting various diseases, including cancer and inflammatory conditions, due to their ability to modulate cellular signaling pathways and gene expression.
As an intermediate, 4,4-Dimethyl-7-ethynyl-1-tetralone plays a crucial role in the chemical synthesis process, enabling the production of RAR antagonists with high affinity and selectivity. This allows for the development of more effective and targeted therapeutic agents in the treatment of various medical conditions.

Upstream product

• 584-08-7 potassium carbonate 
• 166978-46-7 7-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one 
• 1066-54-2 trimethylsilylacetylene 
• 2979-69-3 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone 
• 166978-47-8 7-(trimethylsilyl)ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1-(2H)-one 

Downstream Products

• 171568-44-8 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(trifluoromethylsulfonyl)oxy-2-naphthalenyl)ethynyl]benzoate 
• 166977-92-0 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethynyl]benzoate 
• 188887-70-9 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3-methylphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-72-1 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-methylphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-79-8 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-chlorophenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-81-2 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-methoxyphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-92-5 4-[8-(4-hydroxy-phenyl)-5,5-dimethyl-5,6-dihydro-naphthalen-2-ylethynyl]-benzoic acid ethyl ester 
• 188887-90-3 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3-hydroxyphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-76-5 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-ethylphenyl)-2-naphthalenyl)ethynyl]benzoate 

Relevant articles and documents

High affinity retinoic acid receptor antagonists: Analogs of AGN 193109

A series of high affinity retinoic acid receptor (RAR) antagonists were prepared based upon the known antagonist AGN 193109 (2). Introduction of various phenyl groups revealed a preference for substitution at the para- position relative to the meta-site. Antagonists with the highest affinities for the RARs possessed hydrophobic groups, however, the presence of polar functionality was also well tolerated.

Retinoid-like compounds

The present invention relates to a compound of formula STR1 or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in which X is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH2 --, --CH2 --CH2 --, --C C--, --CH2 --NH--, --COCH2 --, --NHCS--, --CH2 S--, --CH2 O--, --OCH2 --, --NHCH2 -- or --CR5 =CR6 --; Rm and Rk are independently hydrogen, halogen, C1-6 alkyl, hydroxy, C1-6 alkyloxy or nitro; n is zero or one; R4 is --(CH2)t --Y, C1-6 alkyl, or C3-6 cycloalkyl; R1 is --CO2 Z, C1-6 alkyl, CH2 OH, --CONHRy, or CHO; R2 and R3 are independently hydrogen or C1-6 alkyl; Ra and Rb are independently hydrogen or C1-6 alkyl; but when n is one, Ra and Rb together can form a radical of the formula STR2 Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C1-6 alkyl or halogen; Z is hydrogen or C1-6 alkyl; R5, R6 and Ry are independently hydrogen or C1-6 alkyl; and t is zero to six.

Synthesis and characterization of a highly potent and effective antagonist of retinoic acid receptors

-