cis-Atovaquone

Base Information

• Chemical Name: cis-Atovaquone
• CAS No.: 137732-39-9
• Molecular Formula: C22H19ClO3
• Molecular Weight: 366.844
• Mol file: 137732-39-9.mol

Synonyms:cis-Atovaquone;1,4-Naphthalenedione,2-[cis-4-(4-chlorophenyl)cyclohexyl]-3- hydroxy-;Atovaquone EP Impurity B (Atovaquone Related Compound A)

Chemical Property of cis-Atovaquone

Chemical Property:

• Boiling Point: 535.0±50.0 °C(Predicted)
• PKA: 5.01±0.10(Predicted)
• PSA: 54.37000
• Density: 1.349±0.06 g/cm3(Predicted)
• LogP: 5.50510
• Storage Temp.: Room Temperature, under inert atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly, Acetonitrile

Purity/Quality:

> 95% ^*data from raw suppliers

cis-Atovaquone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: cis-Atovaquone is the cis-isomer of Atovaquone (A793500), a hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport.

Technology Process of cis-Atovaquone

There total 6 articles about cis-Atovaquone 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:

atovaquone (94015-53-9) → cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione (137732-39-9) + atovaquone (95233-18-4)

Guidance literature:

With sulfuric acid; at 20 ℃; for 2h; Purification / work up; Resolution of racemate;

Reference yield:

2-hydroxynaphtho-1,4-quinone (83-72-7) + diethyl 4-(trans-4-(4-chlorophenyl)cyclohexyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate → cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione (137732-39-9) + atovaquone (95233-18-4)

Guidance literature:

With sodium persulfate; trifluoroacetic acid; In water; acetonitrile; at 20 ℃; Overall yield = 54 %; Overall yield = 73.7 mg; Inert atmosphere;

DOI:10.1021/jacs.7b05899

Reference yield:

cis-1a-(4-(4-chlorophenyl)cyclohexyl)naphtho[2,3-b]oxirene-2,7(1aH,7aH)dione (1409957-42-1) → cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione (137732-39-9)

Guidance literature:

With sulfuric acid; at 20 ℃; for 0.333333h;

upstream raw materials:

atovaquone

cis-1a-(4-(4-chlorophenyl)cyclohexyl)naphtho[2,3-b]oxirene-2,7(1aH,7aH)dione

cis-2-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone

cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-chloro-1,4-naphthoquinone

Downstream raw materials:

atovaquone

Refernces

• 1、 Dike, Suneel Y.,Singh, Dharmendra,Thankachen, Byju N.,Sharma, Brajesh,Mathur, Pramil K.,Kore, Swapnil,Kumar, Ashok. "A single-pot synthesis of atovaquone: An antiparasitic drug of choice". . p. 618 - 625. Retrieved 2014/06/09.