54531-74-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7272, 1995 DOI: 10.1021/jo00127a036

Upstream product

• 22428-86-0 4,4-<1,2-ethanediylbis(thio)>cyclohexanol 
• 540-63-6 ethane-1,2-dithiol 
• 637-88-7 1,4-Cyclohexanedione 
• 69125-55-9 4-hydroxy-1-methoxy-1-cyclohexene 
• 150-76-5 4-methoxy-phenol 
• 54531-77-0 4,4-<1,2-ethanediylbis(thio)>cyclohexyl benzoate 
• 23510-95-4 4-benzoyloxycyclohexanone 
• 6308-92-5 4-benzoyloxycyclohexanol 

Downstream Products

• 51768-56-0 1,3-dimethoxy-5-ethylbenzene 
• 83638-29-3 1,4-bis(3,5-dimethoxyphenyl)butane 
• 83638-43-1 1-(3,5-dimethoxyphenylethyl)-4-oxocyclohexanol ethylene thioacetal 
• 22428-86-0 4,4-<1,2-ethanediylbis(thio)>cyclohexanol 
• 915027-00-8 [1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl]-(1,4-dithia-spiro[4.5]dec-8-ylidene)-amine 
• 915027-03-1 (S)-2-(4-methoxy-8-oxo-1-azaspiro[4.5]dec-3-en-1-yl)-3-(4-methoxyphenyl)propanal 
• 915027-09-7 (S)-1-[2-hydroxy-1-(4-methoxybenzyl)ethyl]-4-methoxy-1-azaspiro[4.5]dec-3-ene-8-one 
• 915027-11-1 (5S,6R,7R,11S)-6-hydroxy-1-methoxy-5-(4-methoxybenzyl)-6,7,9,10-tetrahydro-3H-7,10a-methanopyrrolo[1,2-a]azocine-8(5H)-one 
• 915027-08-6 (S)-1-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-4-methoxy-1-azaspiro[4.5]dec-3-ene-8-one 
• 915027-02-0 (1'S)-9-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-12-methoxy-1,4-dithia-9-azadispiro[4.2.4.2]tetradec-11-ene 
• 915027-01-9 (1S)-[2-(tert-butyldimethylsiloxy)-1-(4-methoxybenzyl)ethyl]-N-[8-(1-methoxypropa-1,2-dienyl)-1,4-dithiaspiro[4.5]dec-8-yl]amine 

Relevant academic research and scientific papers

Origin of stereocontrol in the construction of the 12-oxatricyclo[6.3.1. 02,7]dodecane ring system by Prins-pinacol reactions

(Chemical Equation Presented) Polycyclic products containing the 12-oxatricyclo[6.3.1.02,7]dodecane moiety having either the trans (8a-e) or cis (9a-e) relative configuration of the oxacyclic bridge and the cis angular substituents are formed s

Oxidation of Alcohols with o-Iodobenzoic Acid (IBX) in DMSO: A New Insight into an Old Hypervalent Iodine Reagent

The ultracentennial 10-I-4 iodinane oxide IBX (3; o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide) represents a new oxidizing reagent that successfully joins to the large family of known oxidants.IBX, in contrast to other valuable oxidants, is inexpensive to prepare and easy to handle, can tolerate moisture and water, and generally gives very good yields.Furthermore, IBX is mild and chemoselective (primary alcohols are converted into aldehydes with no overoxidation to acids; 1,2-diols are converted to α-ketols or α-diketones without oxidative cleavage; amino alcohols are oxidized to amino carbonyls, without protection of the amino group; sensitive heterocycles are not affected; various other functional groups are compatible with IBX oxidation).IBX is versatile (it works in various solvents and it is highly sensitive to temperature variations), and its solutions in DMSO are stable enough to carry out the oxidation reaction easily.

The substrate- and stereoselectivity of microbial reductions of 1,4-dithiaspirodecanones and 1,5-dithiaspiroundecanones

The title spirocyclic ketones, possessing possible substitution patterns 1,4-dithiaspirodecan-6-one (1a), -7-one (3a), and -8-one (5a) and 1,5-dithiaspiroundecan-7-one (2a), -8-one (4a), and -9-one (6a), have been reduced with new strains of yeast (Saccharomyces cerevisiae, JCM 1819 and JCM 2214).Reductions of the prochiral ketones 1a-4a occur with high enantiofacial selectivity on the preparative scale (up to 99percent ee).The product alcohols (1,4-dithiaspirodecan-6-ol (1b) and -7-ol (3b) and 1,5-dithiaspiroundecan-7-ol (2b) and -8-ol (4b)) have theS configuration, as confirmed by 2D COSY experiments of the (S)-MTPA ester of 1b-4b using the configuration correlation model of Mosher.

Studies on the Synthesis of Aphidicolin. The Diels-Alder Route to Spirocyclic Intermediates

The isopropylidene cyclohexylidenemalonates (6; R1=R2=H; R2=OCH2CH2O; and R1, R2=SCH2CH2S) undergo cycloaddition with butadiene, 2-trimethylsilyloxybuta-1,3-diene, and 3-trimethylsilyloxypenta-2,4-diene to give the corresponding spirocyclic adducts (7; R1

Annulation of α-Formyl α,β-Unsaturated Ketones by a Michael Addition-Cyclization Sequence. A Versatile Synthesis of Alicyclic Six-Membered Rings.

The potential generality of the annulation sequence shown in Scheme II (10 -> 11 -> 12 -> 13 -> 14/15) has been examined in model systems.Dehydrogenation of α-formylcyclohexanones 11a-d with 1 equiv of DDQ rapidly produces α,β-unsaturated α-formyl ketones

1,2-Disubstituted Ethanes As Possible Precursors For The Synthesis of Cannabis Spirans

Three possible methods for converting suitable 1,2-disubstituted ethanes into Cannabis spirans have been investigated. 4',5-Dihydroxy-3-methoxybibenzyl underwent intramolecular o-p- and p-p-coupling with ferricyanide in a chloroform-aqueous potassium carbonate system, but yields were low: certain other oxidants did not succeed or gave only traces of product.A method for making 1-hydroxy-1-(3,5-dimethoxyphenylethyl)cyclohexan-4-one ethylene acetal or thioacetal via a Birch reaction is described: despite favourable precedent, acid-catalysed cyclisation led to octahydrophenanthrenones rather than spiro-ketones, whilst N,N-dimethylformamide dineopentyl acetal gave two olefins.Jacquesy's super-asid method for making spirocyclohexenones from a methoxylated bibenzyl was not applicable to the 3,4',5-trimethoxy-case, which would have given cannabispirenone methyl ether, presumably because of protonation of both aromatic systems.