(S)-Fenoprofen

Base Information

• Chemical Name: (S)-Fenoprofen
• CAS No.: 33028-97-6
• Molecular Formula: C15H14 O3
• Molecular Weight: 242.274
• UNII: CR23L7LA3Y
• Nikkaji Number: J245.601J
• ChEMBL ID: CHEMBL251463
• Mol file: 33028-97-6.mol

Synonyms:(S)-Fenoprofen;S-(+)-Fenoprofen;S(+)-fenoprofen;(+)-Fenoprofen;Fenoprofen, (S)-;CR23L7LA3Y;Hydratropic acid, m-phenoxy-, (+)-;UNII-CR23L7LA3Y;(S)-2-(3-Phenoxyphenyl)propionic acid;(+)-2-(3-Phenoxyphenyl)propionic acid;33028-97-6;Benzeneacetic acid, alpha-methyl-3-phenoxy-, (S)-;CHEMBL251463;SCHEMBL4492279;Benzeneacetic acid, alpha-methyl-3-phenoxy-, (alphaS)-;BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, (S)-;BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, (.ALPHA.S)-

Chemical Property of (S)-Fenoprofen

Chemical Property:

• PSA: 46.53000
• LogP: 3.66700
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC=C1)OC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C[C@@H](C1=CC(=CC=C1)OC2=CC=CC=C2)C(=O)O

Technology Process of (S)-Fenoprofen

There total 25 articles about (S)-Fenoprofen 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: 96.0%

(2S)-2-(3-phenoxy-phenyl)-propan-1-ol (1226783-62-5) → (S)-fenoprofen (33028-97-6,31879-05-7,32953-79-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In water; acetonitrile; at 35 ℃; for 26h; aq. phosphate buffer;

DOI:10.1055/s-0030-1258580

Reference yield: 91.0%

1-phenoxy-3-[(R)-1-methylallyl]benzene (1146411-11-1) → (S)-fenoprofen (33028-97-6,31879-05-7,32953-79-0)

Guidance literature:

1-phenoxy-3-[(R)-1-methylallyl]benzene; With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 3h; Inert atmosphere;

With sulfuric acid; In dichloromethane; water; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jo900198b

Reference yield: 81.0%

(S)-benzyl 2-(3-phenoxyphenyl)propanoate → (S)-fenoprofen (33028-97-6,31879-05-7,32953-79-0)

Guidance literature:

With palladium 10% on activated carbon; In methanol; at 25 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja5109084

upstream raw materials:

Fenoprofen

methyl 2-(3-phenoxybenzene)propionate

(1S,2R,3S)-1,2-Dihydroxy-3-(3-phenoxyphenyl)-1-phenylbutane

(1S,2S,3S)-2,3-Epoxy-3-(3-phenoxyphenyl)-1-phenylpropan-1-ol

Downstream raw materials:

C₁₇H₁₉NO₃

Refernces

• 1、 Guan, Zheng-Hui,Ren, Zhi-Hui,Wang, Yuan,Yang, Hui-Yi,Yao, Ya-Hong,Zou, Xian-Jin. "Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids". supporting information. p. 23117 - 23122. Retrieved 2021/09/18.
• 2、 Mandrelli, Francesca,Blond, Aurélie,James, Thomas,Kim, Hyejin,List, Benjamin. "Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol". . p. 11479 - 11482. Retrieved 2019/07/18.