Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

Base Information

• Chemical Name: Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate
• CAS No.: 153559-45-6
• Molecular Formula: C24H28 O3
• Molecular Weight: 364.485
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID50471185
• Wikidata: Q72491035
• Mol file: 153559-45-6.mol

Synonyms:153559-45-6;Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate;Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate;methyl 4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carbonyl)benzoate;Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)benzoate;Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl] benzoate;DYVLPJYIGJZAKF-UHFFFAOYSA-N;C24H28O3;SCHEMBL3982018;DTXSID50471185;AMY24855;BCP08505;MFCD12828199;AKOS015896396;Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-Tetrahydro naphthalene-2-carbonyl)benzoate;AC-24573;AS-11441;CS-0188157;FT-0652504;pentamethyl-2-naphthalenyl)carbonyl]-,methyl;E75997;A809438;Benzoic acid,4-[(5,6,7,8-tetrahydro-3,5,5,8,8-;Methyl4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate;4-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalene-2carbonyl)-benzoic acid methyl ester;methyl 4-(1,1,4,4,7-pentamethyltetralin-6-carbonyl)benzoate;Desmethylene Oxo-bexarotene Methyl Ester

Chemical Property of Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 143-144 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• Boiling Point: 472.829oC at 760 mmHg
• Flash Point: 203.311oC
• PSA: 43.37000
• Density: 1.055
• LogP: 5.36160
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 364.20384475
• Heavy Atom Count: 27
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

DesmethyleneOxo-bexaroteneMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1C(=O)C3=CC=C(C=C3)C(=O)OC)C(CCC2(C)C)(C)C
• Uses: A possible drug candidate in the treatment of cancers. Intermediate in the preparation of tetramethylcyclohexane derivatives as retinoid X receptors modulators.

Technology Process of Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

There total 12 articles about Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.3%

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)

Guidance literature:

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

Reference yield: 82.0%

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)

Guidance literature:

With aluminum (III) chloride;

Reference yield:

Monomethyl terephthalate (1679-64-7) + 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (6683-48-3) → C38H46O2 (1349659-51-3) + 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid (153559-46-7) + methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate (153559-45-6)

Guidance literature:

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;

With hydrogenchloride; water; In dichloromethane; water; at 15 - 20 ℃;

upstream raw materials:

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

4-Methoxycarbonylbenzoyl chloride

2,5-dimethyl-2,5-hexanediol

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

Downstream raw materials:

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

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

bexarotene

C₂₅H₃₀O

Refernces

• 1、 -. "Preparation method of key intermediate of bexarotene". Paragraph 0029-0030. . Retrieved 2017/05/27.
• 2、 -. "PROCESS FOR THE PREPARATION OF HIGHLY PURE BEXAROTENE". Page/Page column 18-19. . Retrieved 2011/12/02.