Ibuprofen alcohol, (-)-

Base Information

• Chemical Name: Ibuprofen alcohol, (-)-
• CAS No.: 114937-30-3
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.301
• UNII: 447XFQ34WK
• Nikkaji Number: J1.360.326J
• Wikidata: Q27258715
• Mol file: 114937-30-3.mol

Synonyms:Ibuprofen alcohol, (-)-;114937-30-3;(S)-2-p-Isobutylphenyl-1-propanol;UNII-447XFQ34WK;447XFQ34WK;Benzeneethanol, beta-methyl-4-(2-methylpropyl)-, (S)-;Benzeneethanol, beta-methyl-4-(2-methylpropyl)-, (betaS)-;(-)-ibuprofen alcohol;SCHEMBL9519111;(S)-2-(4-Isobutylphenyl)propan-1-ol;EN300-6507220;(2S)-2-[4-(2-methylpropyl)phenyl]propan-1-ol;Q27258715;BENZENEETHANOL, .BETA.-METHYL-4-(2-METHYLPROPYL)-, (S)-;BENZENEETHANOL, .BETA.-METHYL-4-(2-METHYLPROPYL)-, (.BETA.S)-

Chemical Property of Ibuprofen alcohol, (-)-

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 145

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)CO
• Isomeric SMILES: C[C@H](CO)C1=CC=C(C=C1)CC(C)C

Technology Process of Ibuprofen alcohol, (-)-

There total 39 articles about Ibuprofen alcohol, (-)- 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: 97.0%

(-)-2-(4-isobutylphenyl)-1-acetoxypropane (194606-27-4) → (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol (114937-30-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0957-4166(97)00237-1

Reference yield: 96.0%

(S)-ethyl 2-(4-isobutylphenyl)propanoate (272458-63-6) → (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol (114937-30-3)

Guidance literature:

With C₃₃H₂₉FeMnN₂O₃P; hydrogen; potassium carbonate; In isopropyl alcohol; at 50 ℃; for 16h; under 37503.8 Torr; Autoclave;

DOI:10.1021/acs.orglett.8b00864

Reference yield: 93.0%

2-(4-isobutylphenyl)propionaldehyde (51407-46-6) → (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol (114937-30-3)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; ethanol; horse liver alcohol dehydrogenase; In phosphate buffer; acetonitrile; for 24h; pH=7.5; Enzymatic reaction;

DOI:10.1039/b712290j

upstream raw materials:

(S)-(+)-methyl 2-(4-isobutylphenyl)propionate

(-)-2-(4-isobutylphenyl)-1-acetoxypropane

Acetic acid (S)-2-(4-isobutyl-phenyl)-3-(toluene-4-sulfonyloxy)-propyl ester

(S)-2-(4-isobutylphenyl)-1,2-propanediol

Downstream raw materials:

(S)-ibuprofen

ibuprofen

(4R)-2-<(1S)-1-(4-(2-Methylpropyl)phenyl)ethyl>thiazolidine-4-carboxylic Acid

(R)-ibuprofene

Refernces

• 1、 Ishibashi, Hiroyuki,Maeki, Momoe,Yagi, Junko,Ohba, Masashi,Kanai, Tae. "A modification of the asymmetric dihydroxylation approach to the synthesis of (S)-2-arylpropanoic acids". . p. 6075 - 6080. Retrieved 1999.
• 2、 Stevenson, Cheryl D.,Cashion, Daniel K.. "Chiral Recognition between a Substituted Cyclooctatetraene Dianion and a Half Crown Ether Substituted with Ibuprofen". . p. 7588 - 7594. Retrieved 2000.
• 3、 -. "MANGANESE-CATALYSED HYDROGENATION OF ESTERS". Page/Page column 34; 41; 42. . Retrieved 2019/08/06.
• 4、 Le, Linh,Liu, Jiachen,He, Tianyi,Malek, Jack C.,Cervarich, Tia N.,Buttner, John C.,Pham, John,Keith, Jason M.,Chianese, Anthony R.. "Unexpected CNN-to-CC Ligand Rearrangement in Pincer-Ruthenium Precatalysts Leads to a Base-Free Catalyst for Ester Hydrogenation". . . Retrieved 2019/08/13.