Deacylketoconazole

Base Information

• Chemical Name: Deacylketoconazole
• CAS No.: 67914-61-8
• Molecular Formula: C24H26Cl2N4O3
• Molecular Weight: 489.401
• European Community (EC) Number: 267-745-3
• UNII: P7P4A1FD7Z
• ChEMBL ID: CHEMBL372799
• Nikkaji Number: J285.416C
• Mol file: 67914-61-8.mol

Synonyms:de-N-acetylketoconazole;deacetylated ketoconazole;deacylketoconazole;R 39 519;R 39519;R-39519

Chemical Property of Deacylketoconazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 173℃
• Boiling Point: 699.7°Cat760mmHg
• PKA: 8.99±0.10(Predicted)
• Flash Point: 376.9°C
• PSA: 60.78000
• Density: 1.39g/cm³
• LogP: 4.34070
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 488.1381961
• Heavy Atom Count: 33
• Complexity: 621

Purity/Quality:

97% ^*data from raw suppliers

DeacetylKetoconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Isomeric SMILES: C1CN(CCN1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Uses: Ketoconazole derivative.

Technology Process of Deacylketoconazole

There total 7 articles about Deacylketoconazole 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: 99.0%

ketoconazole (65277-42-1) → 4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine (67914-61-8)

Guidance literature:

With sodium hydroxide; In methanol; Heating;

DOI:10.1016/j.bmc.2008.05.008

Reference yield: 25.0%

1-Formyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine (67914-70-9,85058-44-2,133345-19-4) → trans-Desacetylketoconazole (67914-61-8,75052-06-1,89929-33-9,133345-17-2)

Guidance literature:

With potassium hydroxide; In butan-1-ol; for 24h; Heating;

DOI:10.1002/jhet.5570270739

Reference yield:

cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-(1,3-dioxolan-4-yl)]methyl methanesulfonate (61397-61-3) → 4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine (67914-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 5 h

2: 71 percent / NaOH / butan-1-ol / Heating

With sodium hydroxide; sodium hydride; In butan-1-ol;

DOI:10.1021/jm00373a015

upstream raw materials:

1-Formyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine

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

1-Formyl-4-(4-hydroxyphenyl)piperazine

4-(p-methoxyphenyl)piperazine dihydrochloride

Downstream raw materials:

1-Methyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine

1-Methyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine

1-Formyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine

1-Methanesulfonyl-4-<4-<-1,3-dioxolan-4-yl>methylenoxy>phenyl>piperazine