27425-93-0

Basic information

• Product Name: Cholesta-4,6-diene
• Synonyms: Cholesta-4,6-diene
• CAS NO: 27425-93-0
• Molecular Formula: C₂₇H₄₄
• Molecular Weight: 368.64
• Mol File: 27425-93-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 458°C at 760 mmHg
• Flash Point: 225.2°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 3.86E-08mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: Cholesta-4,6-diene(CAS DataBase Reference)
• NIST Chemistry Reference: Cholesta-4,6-diene(27425-93-0)
• EPA Substance Registry System: Cholesta-4,6-diene(27425-93-0)

Safety Data

• Hazardous Substances Data: 27425-93-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H44/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h11-13,19-20,22-25H,6-10,14-18H2,1-5H3

Upstream product

• 91-22-5 quinoline 
• 6213-04-3 5,6β-dibromo-5α-cholestane 
• 5863-62-7 5.6α-dibromo-5β-cholestane 
• 66014-22-0 6β-Chloro-5-hydroxy-5α-cholestane 
• 333-20-0 potassium thioacyanate 
• 21489-86-1 4,5-secocholest-3-yn-5-one 
• 20230-22-2 5,6β-epoxy-5β-cholestane 
• 20230-22-2 5α,6α-epoxycholestane 

Downstream Products

• 481-21-0 cholestane 
• 481-20-9 5β-cholestane 
• 6215-42-5 cholest-5-en-4,7-dione 
• 747-90-0 3,5-cholestadiene 
• 16137-58-9 4β-Aethoxy-5β,7β-cyclocholestan 
• 19317-92-1 Cholestadien-(4,8) 
• 566-90-5 cholest-4-en-3α-ol 
• 517-10-2 allocholesterol 
• 16137-59-0 5β,7β-Cyclo-cholesten-(3) 
• 19318-00-4 5β,7α-Cyclocholestanon-(4) 
• 16137-61-4 5,7β-Cyclocholestanon-(3) 
• 562-57-2 4α-Hydroxy-5β,7β-cyclocholestan 
• 19404-83-2 3α-Hydroxy-5β,7β-cyclocholestan 
• 16137-62-5 5,7β-Cyclo-5β-cholestan-3β-ol 

Relevant articles and documents

Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization

The reaction of tetramethyldiamidophosphoric acid chloride with epoxides in the presence of a trace amount of water furnished 1,3-dienes in good yield. The conversion works with open chain and cyclic epoxides. A C-C bond cleavage reaction occurs if the epoxide contains a quaternary carbon. Application of this method to epoxy sterols afforded ring A aromatic steroids in good yield. The aromatization works via dienol-benzene rearrangements and is independent of the C-3 stereochemistry.

Synthesis of Cholestenothiazoles and Cholestanooxazolidine

4β,5-Epoxy-5β-cholestan-3-one (I) reacts with thiourea to afford 5β-hydroxycholest-3-eno-2'-aminothiazole (II) while with thiacetamide it furnishes 3,5-cholestadieno-2'-methylthiazole (III) and 5β-hydroxycholest-3-eno-2'-methylthiazole (IV). 6β-Chloro-5-hydroxy-5α-cholestane (V) on treatment with KSCN in dimethylformamide gives cholesta-4,6-diene (VI), 5α-chloestan-6-one (VII), 5-hydroxy-5α-cholestan-6α-yl isothiocyanate (VIII), 5-hydroxy-5α-cholestan-6-one (IX) and 5α-cholestano-2'-thiooxooxazolidine (X).The structures of these compounds have been established on the basis of spectral properties, analytical data and also by direct comparison with authentic samples where available.