5alpha-Cholestan-3-one

Base Information

• Chemical Name: 5alpha-Cholestan-3-one
• CAS No.: 566-88-1
• Molecular Formula: C27H46 O
• Molecular Weight: 386.662
• DSSTox Substance ID: DTXSID001016294
• Nikkaji Number: J149.976I
• Wikidata: Q27102587
• Metabolomics Workbench ID: 34464
• ChEMBL ID: CHEMBL69941
• Mol file: 566-88-1.mol

Synonyms:5-alpha-cholestan-3-one;coprostanone;coprostanone, (5alpha)-isomer;coprostanone, (5beta)-isomer

Chemical Property of 5alpha-Cholestan-3-one

Chemical Property:

• Vapor Pressure: 2.16E-08mmHg at 25°C
• Melting Point: 128-133 °C
• Boiling Point: 434.1°Cat760mmHg
• Flash Point: 230.5°C
• PSA: 17.07000
• Density: 1.038g/cm³
• LogP: 7.67680
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly)
• Water Solubility.: Insoluble in water.
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 386.354866087
• Heavy Atom Count: 28
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

5-α-Cholestan-3-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
• Uses: 5alpha-Cholestan-3-one

Technology Process of 5alpha-Cholestan-3-one

There total 57 articles about 5alpha-Cholestan-3-one 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: 82.0%

(2R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2-phenylselanyl-hexadecahydro-cyclopenta[a]phenanthren-3-one (115073-73-9) → Cholestanol (80-97-7) + dihydrocholesterone (566-88-1)

Guidance literature:

With methanol; sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/jo00251a028

Reference yield: 75.0%

Cholest-4-en-3-one (601-57-0) → dihydrocholesterone (566-88-1) + coprostanone (601-53-6) + 5β-cholestan-3-ol (566-84-7)

Guidance literature:

With hydrogen; Cu/Al₂O₃; In toluene; at 60 ℃; under 760 Torr;

DOI:10.1021/jo00013a054

Reference yield: 40.0%

epicholesterol (474-77-1) → Cholest-4-en-3-one (601-57-0) + dihydrocholesterone (566-88-1)

Guidance literature:

nickel; In xylene; at 135 - 140 ℃; for 4h; Heating;

upstream raw materials:

cholest-1-en-3-one

Cholestanol

3-β-cholestanol

2β-(trimethylsilyl)-2α,3α-epoxycholestane

Downstream raw materials:

2α-bromo-5α-cholestan-3-one

2-hydroxymethylene-5α-cholestan-3-one

3,3-Dimethoxy-5α-cholestan

(5α-cholestan-3α-yl)-cyclohexyl-amine

Refernces

• 1、 Barnych, Bogdan,Vatèle, Jean-Michel. "One-Pot Bi(OTf)catalyzed oxidative deprotection of tert -butyldimethyl silyl ethers with TEMPO and co-oxidants". experimental part. p. 2048 - 2052. Retrieved 2011/10/19.
• 2、 Wong, Man-Kin,Chung, Nga-Wai,He, Lan,Wang, Xue-Chao,Yan, Zheng,Tang, Yeung-Chiu,Yang, Dan. "Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ". . p. 6321 - 6328. Retrieved 2007/10/03.