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

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 5α,6α-epoxycholestane 
• 20230-22-2 5,6β-epoxy-5β-cholestane 

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.

Unexpected Cyclisation of an Acetylenic Acetal: Vinyl Cation Capture by Internally transferred Hydride

The acetylenic acetal (2) is converted in 90 percent yield to a mixture of cholesta-3,5- and 4,6-dienes on reflux in toluene containing toluene-p-sulphonic acid.

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.

Reactions of steroidal 5,6-epoxides and cyclohexene oxide with aluminum alkoxides

The isomeric 5,6α- and 5,6β-epoxycholestanes, in addition to an analogous series of compounds substituted at C-3 with hydroxy (α or β stereochemistry) or ethylene ketal groups, have been treated with aluminum isopropoxide or tert-butoxide.The latter series of reactions did not give identifiable material, but aluminum isopropoxide gave products derived from epoxide opening and rearrangement in all cases.With epoxides unsubstituted at C-3, aluminum isopropoxide functioned as a Lewis acid in promoting epoxide rearrangements.In the presence of a C-3 alcohol function, additional products were obtained arising from fragmentation of the C-4,C-5 bond, or from β-elimination of the epoxide involving the loss of a C-7 hydrogen.Meerwein-Pondorff reduction of product carbonyl groups was also observed.C-3 ketal substituted epoxides were rearranged cleanly to 6-hydroxy-Δ4-3-ketones.Cyclohexene oxide reacted with aluminum isopropoxide (but not with tert-butoxide) to give two products arising from epoxide addition reactions.Structures for these products are proposed based on their 13C nmr spectra, and a possible route for their formation is presented.None of the epoxides examined in this study reacted with magnesium methoxide.