trans-Ketoconazole

Base Information

• Chemical Name: trans-Ketoconazole
• CAS No.: 142128-58-3
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₄
• Molecular Weight: 531.439
• UNII: 3INP7D7XI3,2EWW9YYR6A
• ChEMBL ID: CHEMBL328863
• Metabolomics Workbench ID: 56950
• Nikkaji Number: J220.792C
• Wikidata: Q27121165
• Mol file: 142128-58-3.mol

Synonyms:trans-Ketoconazole;83374-59-8;(2R,4R)-ketoconazole;Ketoconazole, trans-;rac-trans-Ketoconazole;Ketoconazole, trans-(+/-)-;3INP7D7XI3;RS-36745;CHEMBL328863;142128-58-3;CHEBI:48344;R-44319;1-[4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone;1-Acetyl-4-(4-(((2RS,4RS)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine;1-acetyl-4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine;Piperazine, 1-acetyl-4-(4-(((2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, rel-;Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, trans-;Piperazine, 1-acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel-;UNII-3INP7D7XI3;(2R,4R)-trans-Ketoconazole;Ketoconazole impurity C [EP];2EWW9YYR6A;Ketoconazole, (2R,4R)-;HMS3869I03;BDBM50004441;CCG-36052;PD086247;KETOCONAZOLE IMPURITY C [EP IMPURITY];EN300-251596;Q27121165;(2R,4R)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine;Piperazine, 1-acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-;Piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, (2R-trans)-;rac-1-[4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Chemical Property of trans-Ketoconazole

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 530.1487608
• Heavy Atom Count: 36
• Complexity: 735

Purity/Quality:

(2R,4R)-trans-Ketoconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Isomeric SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

Technology Process of trans-Ketoconazole

There total 19 articles about trans-Ketoconazole 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: 54.0%

1H-imidazole (288-32-4) + (2R,4R)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane (142128-66-3) → (2R,4R)-Ketoconazole (142128-58-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl acetamide; for 4h; Heating;

DOI:10.1021/jm00093a015

Reference yield:

ketokonazole → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With Beckman P/ACE MDQ Capillary Electrophoresis System equipped fused-silica capillaries (Polymicro Technologies, Phoenix, Arizona) of 50-μm ID cut with sulfobutyl ether β-cyclodextrin as chiral selector; In aq. buffer; at 25 ℃; pH=2.5; Concentration; pH-value; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22777

Reference yield:

ketoconazole (65277-42-1) → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With cellulose (3,5-dimethylphenylcarbamate) coated reduced graphene oxide(at)silica gel; In hexane; at 25 ℃; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.22976

upstream raw materials:

trans-<2-(2,4-Dichlorophenyl)-2-<1H-imidazol-1-yl>methyl-(1,3-dioxolan-4-yl)>methyl methanesulfonate

N-acetyl-N'-(4-hydroxyphenyl)piperazine

1-(4-hydroxy-phenyl)-piperazine dihydrobromide

1-(4-Acetoxyphenyl)-4-acetylpiperazine

Downstream raw materials:

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-methanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-methanesulfonylmethanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(thiophene-2-sulfonyl)piperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(1-methylimidazol-2-ylsulfonyl)piperazine

Refernces

• 1、 Li, Yuanyuan,Li, Qiang,Zhu, Nan,Gao, Zhuxian,Ma, Yulong. "Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds". . p. 996 - 1004. Retrieved 2018/07/29.
• 2、 Camps, Pelayo,Farres, Xavier,Garcia, Luisa,Ginesta, Joan,Pascual, Jaume,et al.. "Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin". . p. 1283 - 1294. Retrieved 2007/10/03.