N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide

Base Information

• Chemical Name: N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
• CAS No.: 134865-74-0
• Molecular Formula: C19H21NO
• Molecular Weight: 279.38
• DSSTox Substance ID: DTXSID40424983
• Nikkaji Number: J2.819.234G
• Wikidata: Q82237732
• ChEMBL ID: CHEMBL1402435
• Mol file: 134865-74-0.mol

Synonyms:N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide;Tocris-1034;NCGC00024953-01;CHEMBL1402435;DTXSID40424983;N-(4alpha-Phenyl-1,2,3,4-tetrahydronaphthalene-2beta-yl)propanamide

Chemical Property of N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide

Chemical Property:

• Vapor Pressure: 2.22E-09mmHg at 25°C
• Melting Point: 166 °C
• Refractive Index: 1.595
• Boiling Point: 480.1°Cat760mmHg
• PKA: 15.87±0.40(Predicted)
• Flash Point: 292°C
• PSA: 29.10000
• Density: 1.11g/cm³
• LogP: 4.05040
• Storage Temp.: Store at RT
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 279.162314293
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

98%,99%, ^*data from raw suppliers

4P-PDOT ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)NC1CC(C2=CC=CC=C2C1)C3=CC=CC=C3
• Isomeric SMILES: CCC(=O)N[C@H]1C[C@@H](C2=CC=CC=C2C1)C3=CC=CC=C3
• Uses: 4-P-PDOT is a MT2 melatonin receptor ligand.

Technology Process of N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide

There total 56 articles about N-[(2S,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide 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: 100.0%

(+/-)-N-(4-phenyl-3,4-dihydronaphthalen-2-yl) propionamide (1005765-07-0) → (+/-)-cis-N-(4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl) propionamide (134865-74-0,620170-78-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 0.0833333h; under 3040.2 Torr; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/asia.200900441

Reference yield: 91.0%

(S)-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide (1353637-88-3) → (+)-(2S,4S)-cis-N-(4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide (1350817-02-5,134865-74-0,620170-78-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 0.166667h; under 3040.2 Torr;

DOI:10.1039/c1ob06369c

Reference yield: 85.0%

(R)-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide (1353637-94-1) → (-)-(2R,4R)-cis-N-(4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide (1350817-03-6,134865-74-0,620170-78-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 0.166667h; under 3040.2 Torr;

DOI:10.1039/c1ob06369c

upstream raw materials:

propionyl chloride

4-phenyl-2-(2'-bromopropenoylamido)tetralin

propionic acid anhydride

4-phenyl-2-tetralone

Refernces

• 1、 Lucarini, Simone,Bartolucci, Silvia,Bedini, Annalida,Gatti, Giuseppe,Orlando, Pierfrancesco,Piersanti, Giovanni,Spadoni, Gilberto. "Synthesis and configuration determination of all enantiopure stereoisomers of the melatonin receptor ligand 4-phenyl-2-propionamidotetralin using an expedient optical resolution of 4-phenyl-2-tetralone". scheme or table. p. 305 - 313. Retrieved 2012/02/02.
• 2、 Lucarini, Simone,Alessi, Matteo,Bedini, Annalida,Giorgini, Giorgia,Piersanti, Giovanni,Spadoni, Gilberto. "Diastereo- and enantioselective hydrogenation of a challenging enamide derived from 4-phenyl-2-tetralone: An appealing shortcut towards enantiopure cis-2-aminotetraline derivatives". scheme or table. p. 550 - 554. Retrieved 2010/08/13.