Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate

Base Information

• Chemical Name: Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate
• CAS No.: 153559-48-9
• Molecular Formula: C25H30 O2
• Molecular Weight: 362.512
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID10439084
• Nikkaji Number: J1.601.935F
• Wikidata: Q82254970
• Mol file: 153559-48-9.mol

Synonyms:153559-48-9;Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate;Methyl 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate;Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester;SCHEMBL2594347;DTXSID10439084;AKOS015896398;DS-4602;Methyl 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl]benzoate;FT-0659262;C72903;A809440;methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronapthalene-2-yl)vinyl)benzoate;Methyl 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoate;Methyl 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]benzoate;Methyl4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate;4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)vinyl]benzoic acid methyl ester

Chemical Property of Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate

Chemical Property:

• Vapor Pressure: 4.32E-09mmHg at 25°C
• Melting Point: 160-161 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• Boiling Point: 472.3oC at 760 mmHg
• Flash Point: 173.2oC
• PSA: 26.30000
• Density: 1.007g/cm3
• LogP: 6.19210
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 362.224580195
• Heavy Atom Count: 27
• Complexity: 565

Purity/Quality:

99% ^*data from raw suppliers

MethylBexarotenate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1C(=C)C3=CC=C(C=C3)C(=O)OC)C(CCC2(C)C)(C)C
• Uses: Methyl Bexarotenate is a related compound of Bexarotene (B336750), which is an antineoplastic agent and a selective retinoid X receptor (RXR) agonist.

Technology Process of Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate

There total 21 articles about Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)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: 88.0%

(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-boronic acid (169126-64-1) + 4-(1-(trifluoromethanesulfonyloxy)vinyl)benzoic acid methyl ester (199188-36-8) → methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate (153559-48-9)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1021/jo0103064

Reference yield: 73.0%

bexarotene (153559-49-0) + methyl iodide (74-88-4) → methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate (153559-48-9)

Guidance literature:

With potassium carbonate; In acetone; at 23 ℃; for 18h;

DOI:10.1002/anie.201805396

Reference yield: 69.0%

Methyltriphenylphosphonium bromide (1779-49-3) + methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate (153559-45-6) → methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate (153559-48-9)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; at -30 - 0 ℃; for 0.5h; Inert atmosphere;

methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate; In tetrahydrofuran; at -30 - 0 ℃; for 1h;

upstream raw materials:

Methyltriphenylphosphonium bromide

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

(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-boronic acid

4-(1-(trifluoromethanesulfonyloxy)vinyl)benzoic acid methyl ester

Downstream raw materials:

bexarotene

Refernces

• 1、 Lee, Jong Bong,Zgair, Atheer,Malec, Jed,Kim, Tae Hwan,Kim, Min Gi,Ali, Joseph,Qin, Chaolong,Feng, Wanshan,Chiang, Manting,Gao, Xizhe,Voronin, Gregory,Garces, Aimie E.,Lau, Chun Long,Chan, Ting-Hoi,Hume, Amy,McIntosh, Tecashanell M.,Soukarieh, Fadi,Al-Hayali, Mohammed,Cipolla, Elena,Collins, Hilary M.,Heery, David M.,Shin, Beom Soo,Yoo, Sun Dong,Kagan, Leonid,Stocks, Michael J.,Bradshaw, Tracey D.,Fischer, Peter M.,Gershkovich, Pavel. "Lipophilic activated ester prodrug approach for drug delivery to the intestinal lymphatic system". . p. 10 - 19. Retrieved 2018/07/25.
• 2、 -. "NOVEL BEXAROTENE ANALOGS". Page/Page column 19. . Retrieved 2011/09/19.