Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate

Base Information

• Chemical Name: Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate
• CAS No.: 83303-57-5
• Molecular Formula: C18H16O2
• Molecular Weight: 264.324
• DSSTox Substance ID: DTXSID60509281
• Nikkaji Number: J2.836.886K
• Mol file: 83303-57-5.mol

Synonyms:Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate;83303-57-5;DTXSID60509281

Chemical Property of Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 264.115029749
• Heavy Atom Count: 20
• Complexity: 379

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=CC=CC=C2C(C1)C3=CC=CC=C3

Technology Process of Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate

There total 5 articles about Methyl 4-phenyl-3,4-dihydronaphthalene-2-carboxylate 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: 95.0%

methyl 1-(hydroxy(phenyl)methyl)-2-phenylcyclopropane-1-carboxylate → methyl 1,2-dihydro-1-phenylnaphthalene-3-carboxylate (83303-57-5)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 83 ℃; for 1h; Inert atmosphere;

DOI:10.1246/cl.2010.194

Reference yield: 33.0%

methyl (E)-2-((E)-benzylidene)-4-phenylbut-3-enoate → 4-phenyl-3,4-dihydronaphthalene-2-carboxylic acid (108979-92-6) + methyl 1,2-dihydro-1-phenylnaphthalene-3-carboxylate (83303-57-5)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at 0 - 50 ℃; for 18h; Inert atmosphere;

DOI:10.1002/adsc.201301169

Reference yield:

4,4-diphenylbutanoic acid (14578-67-7) → methyl 1,2-dihydro-1-phenylnaphthalene-3-carboxylate (83303-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h

2: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h

3: 1.) NaBH₄ / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, rt, 3-4 h

4: 73 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating

With sodium tetrahydroborate; PPA; sodium hydride; toluene-4-sulfonic acid; hydroquinone; In benzene;

upstream raw materials:

4,4-diphenylbutanoic acid

4-phenyl-3,4-dihydronaphthalen-1(2H)-one

Downstream raw materials:

(1aS,3R,7bR)-1,3-Diphenyl-1,2,3,7b-tetrahydro-1-aza-cyclopropa[a]naphthalene-1a-carboxylic acid methyl ester

(3aS,5R,9bS)-5-Phenyl-1,4,5,9b-tetrahydro-benzo[e]indazole-3a-carboxylic acid methyl ester

(3S,3aS,5S,9bS)-2,3,5-Triphenyl-2,3,5,9b-tetrahydro-4H-benzo[e]isoindole-1,1,3a-tricarboxylic acid trimethyl ester

methyl 4-phenyl-2-naphthoate