delta(sup5)-Cholestenone

Base Information

• Chemical Name: delta(sup5)-Cholestenone
• CAS No.: 601-54-7
• Molecular Formula: C27H44 O
• Molecular Weight: 384.646
• Hs Code.: 2937900090
• NSC Number: 118979
• Mol file: 601-54-7.mol

Synonyms:delta(sup5)-Cholestenone;10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;.delta.(sup5)-Cholestenone;NSC-118979;SCHEMBL1918692;(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;MFCD00009940;NSC118979;LS-53138;SY257683;FT-0670619;WLN: L E5 B666 OV LUTJ A1 E1 FY1&3Y1&1

Chemical Property of delta(sup5)-Cholestenone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 477.368°C at 760 mmHg
• Flash Point: 200.455°C
• PSA: 17.07000
• Density: 0.985g/cm³
• LogP: 7.59690
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 630

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Keto cholesterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(=O)C4)C)C

Technology Process of delta(sup5)-Cholestenone

There total 43 articles about delta(sup5)-Cholestenone 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: 100.0%

cholesterol (57-88-5) → Cholest-5-en-3-one (601-54-7)

Guidance literature:

With C₄₀H₃₆Cl₂FeN₂P₂Ru; potassium tert-butylate; In toluene; tert-butyl alcohol; at 145 ℃; for 3h; Inert atmosphere;

DOI:10.1021/om201189r

Reference yield: 96.0%

oxime of 5-cholesten-3-one (63085-02-9) → Cholest-5-en-3-one (601-54-7)

Guidance literature:

With Montmorillonite K-10 clay; pyridinium chlorochromate; for 0.0333333h; microwave irradiation;

Reference yield: 86.0%

cholesterol (765935-41-9) → Cholest-5-en-3-one (601-54-7)

Guidance literature:

With ammonium dichromate(VI); aluminum(III) hydrogen sulfate; silica gel; In hexane; at 20 ℃; for 0.5h;

DOI:10.1070/mc2003v013n06abeh001847

upstream raw materials:

(5R,6R)-5,6-Dibromo-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

cholesterol

cholest-4-en-3-one

5,6β-dibromo-5α-cholestan-3-one

Downstream raw materials:

Cholest-4-en-3-one

oxime of 5-cholesten-3-one

epicholesterol-3β-d1

3-²H-cholesterol

Refernces

• 1、 Gonzalez-Hernandez,Canedo,Grande. "Classic and multivariate modeling treatment of the kinetics and mechanism of isomerization of 5-cholesten-3-one catalyzed by sodium ethoxide". . p. 38 - 47. Retrieved 2006.
• 2、 Vasil'tsov,Zaitsev,Mikhaleva,Shmidt,Afonin. "Annelation of the pyrrole to the steroid skeleton using the Trofimov reaction". . p. 60 - 64. Retrieved 2002.
• 3、 Huang, Yanmin,Cui, Jianguo,Li, Ying,Fan, Lei,Jiao, Yanxiao,Su, Shaoyang. "Syntheses and antiproliferative activity of some sulfated hydroximinosterols". . p. 409 - 414. Retrieved 2013.
• 4、 Nikitas, Nikolaos F.,Tzaras, Dimitrios Ioannis,Triandafillidi, Ierasia,Kokotos, Christoforos G.. "Photochemical oxidation of benzylic primary and secondary alcohols utilizing air as the oxidant". supporting information. p. 471 - 477. Retrieved 2020/02/13.