4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone

Base Information

• Chemical Name: 4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone
• CAS No.: 43076-30-8
• Molecular Formula: C32H39NO2
• Molecular Weight: 469.667
• Hs Code.: 2933399090
• European Community (EC) Number: 256-074-1
• UNII: W5XZU6S762
• DSSTox Substance ID: DTXSID90195676
• Nikkaji Number: J548.119H
• Wikidata: Q83068701
• Pharos Ligand ID: MGUUDAZ2HHLK
• Metabolomics Workbench ID: 144699
• ChEMBL ID: CHEMBL205154
• Mol file: 43076-30-8.mol

Synonyms:terfenadone;43076-30-8;4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone;1-(4-tert-butylphenyl)-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butan-1-one;EINECS 256-074-1;1-(4-(tert-Butyl)phenyl)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butan-1-one;CHEMBL205154;W5XZU6S762;4'-TERT-BUTYL-4-[4-(HYDROXYBENZHYDRYL)PIPERIDINO]BUTYROPHENONE;1-(4-(1,1-Dimethylethyl)phenyl)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butan-1-one;1-Butanone, 1-(4-(1,1-dimethylethyl)phenyl)-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-;1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-butanone;1-(4-(1,1-DIMETHYLETHYL)PHENYL)-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-BUTANONE;1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-one (Terfenadone);TERFENADINONE;UNII-W5XZU6S762;MLS006010685;SCHEMBL11364486;DTXSID90195676;MDL 9917;VUF 4590;VUF-4590;BDBM50183084;SMR004701666;TERFENADINE IMPURITY A [EP IMPURITY];W-110981;4'-tert-Butyl-4-[4-(hydroxybenzhydryl)piperidino]putyrophenone;4'-tert-butyl-4-[4-(hydroxydiphenylmethyl)piperidinyl]butyrophenone;1-(4-(tert-butyl)phenyl)-4-(4-(hydroxydiphenylmethyl) piperidin-1-yl)butan-1-one;1-(4-tert-butylphenyl)-4-[4-[hydroxy(diphenyl)methyl]-1-piperidyl]butan-1-one;4'-tert-butyl-4-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]butyrophenone;4-(4'-(Hydroxydiphenylmethyl)piperidin-1-yl)-1-(4-tert-butylphenyl)butan-1-one

Chemical Property of 4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone

Chemical Property:

• Melting Point: 175 °C
• Boiling Point: 624.5°Cat760mmHg
• PKA: 13.32±0.29(Predicted)
• Flash Point: 331.5°C
• PSA: 40.54000
• Density: 1.082g/cm³
• LogP: 6.53300
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 469.298079487
• Heavy Atom Count: 35
• Complexity: 621

Purity/Quality:

99% ^*data from raw suppliers

Terfenadone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
• Uses: Terfenadone, is the first nonsedating antihistamine for the treatment of allergic rhinitis. It is also the derivative of Terfenadine (T114500). Terfenadine, has been also identified to be an inhibitor of human CD81-receptor HCV-E2 interaction.

Technology Process of 4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone

There total 6 articles about 4'-tert-Butyl-4-(4-(hydroxybenzhydryl)piperidino)butyrophenone 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: 79.0%

terfenadine (50679-08-8) → 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone (43076-30-8,76815-60-6)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; triethylamine; In acetone; at 150 ℃; Flow reactor;

DOI:10.1021/acs.oprd.7b00190

Reference yield: 75.0%

C18H21NO (115-46-8) + 1-(4-tert-Butyl-phenyl)-4-iodo-butan-1-one → 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone (43076-30-8,76815-60-6)

Guidance literature:

With potassium carbonate; In butanone; Heating;

DOI:10.1016/0223-5234(93)90009-4

Reference yield: 69.0%

C18H21NO (115-46-8) + 4'-tert-butyl-4-chlorobutyrophenone (43076-61-5) → 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone (43076-30-8,76815-60-6)

Guidance literature:

With sodium carbonate; sodium iodide; In N,N-dimethyl-formamide; for 24h; Reflux;

DOI:10.1016/j.tet.2008.09.098

upstream raw materials:

C₁₈H₂₁NO

terfenadine

4'-tert-butyl-4-chlorobutyrophenone

tert-butylbenzene

Downstream raw materials:

4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid

terfenadine

Refernces

• 1、 Labes, Ricardo,Battilocchio, Claudio,Mateos, Carlos,Cumming, Graham R.,De Frutos, Oscar,Rincón, Juan A.,Binder, Kellie,Ley, Steven V.. "Chemoselective Continuous Ru-Catalyzed Hydrogen-Transfer Oppenauer-Type Oxidation of Secondary Alcohols". supporting information. p. 1419 - 1422. Retrieved 2017/09/23.
• 2、 Perlmutter, Jessamyn I.,Forbes, Lauren T.,Krysan, Damian J.,Ebsworth-Mojica, Katherine,Colquhoun, Jennifer M.,Wang, Jenna L.,Dunman, Paul M.,Flaherty, Daniel P.. "Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus". . p. 8540 - 8562. Retrieved 2014/12/11.