139599-69-2

Upstream product

• 139599-68-1 (3-methoxybenzyl)(phenyl)sulfide 
• 6971-51-3 3-methoxybenzyl alcohol 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 108-98-5 thiophenol 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 21875-72-9 1-(4-methoxy-phenyl)-2-phenylsulfanyl-ethanone 
• 36734-52-8 1-(4-nitrophenyl)-2-(phenylthio)ethan-1-one 
• 6099-23-6 1-(phenylsulfinyl)acetophenone 
• 58936-74-6 1-(4-methoxyphenyl)-2-(phenylsulfinyl)ethan-1-one 
• 73689-75-5 2-benzenesulfinyl-1-(4-nitrophenyl)ethanone 

Downstream Products

• 124236-83-5 (RS,RS)-1-(3'-methoxyphenyl)ethyl phenyl sulfoxide 
• 124236-83-5 (RS,SR)-1-(3'-methoxyphenyl)ethyl phenyl sulfoxide 
• 129527-19-1 1-methoxy-3-((phenylsulfonyl)methyl)benzene 
• 139599-70-5 (1RS,3'SR,2RS,3a'SR,7a'SR)-3-t-butoxy-2-(3''-methoxyphenyl)-3a'-methyl-2',3',3a',4',7',7a'-hexahydro-spiroinden>-6'(1'H)-one 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

A route to benzylic arylsulfoxides from β-ketosulfoxides

The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.

Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides

The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.

The Structure and Function of Estrogens. XI. Synthesis of (+/-)-7(8->11α)abeo-Estradiol and its 9,11-Didehydro Derivative

Two approaches to the synthesis of (+/-)-7(8->11α)abeo-estra-1,3,5(10)triene-3,17β-diol (2a) from (+/-)-1β-t-butoxy-7aβ-methyl-2,3,3aα,6,7,7a-hexahydro-1H-inden-5(4H)-one (11) were studied.A pathway involving 6-alkylation of (11) with 2-(3'-methoxyphenyl)ethyl halides or sulfonate esters was unsuccessful, but conjugate addition of 3-methoxybenzyl nucleophiles with (+/-)-1β-t-butoxy-7aβ-methyl-6-methylene-2,3,3aα,6,7,7a-hexahydro-1H-inden-5(4H)-one (18), prepared from (11), led to (+/-)-1β-t-butoxy-6α--7aβ-methyl-2,3,3aα,6,7,7a-hexahydro-1H-inden-5(4H)-one (10a).Acid-catalyzed cyclization of (10a) afforded (+/-)-17β-t-butoxy-3-methoxy-7(8->11)abeo-estra-1,3,5(10),9(11)-tetraene (29) which upon lithium/ammonia reduction in the presence of diphenylmethane gave (+/-)-17β-t-butoxy-3-methoxy-7(8->11α)abeo-estra-1,3,5(10)-triene (31).Deprotection of (31) and (29) afforded (+/-)-7(8->11α)abeo-estra-1,3,5(10)-triene-3,17β-diol (2a) and (+/-)-7(8->11)abeo-estra-1,3,5(10),9(11)-tetraene-3,17β-diol (32), respectively. Alternatively, reaction of (+/-)-1β-t-butoxy-7aβ-methyl-6-methylene-2,3,3aα,6,7,7a-hexahydro-1H-inden-5(4H)-one (18) with 3-methoxybenzyl phenyl sulfoxide (23a) gave (1RS,3'SR,2RS,3a'SR,7a'SR)-3'-t-butoxy-2-(3''-methoxyphenyl)-3a'-methyl-2',3',3a',4',7',7a'-hexahydrospiroinden>-6'(1'H)-one (26), reductive cleavage of which with lithium/ammonia afforded (10a). The relative stereochemistries of (31) and of the spiro cyclopropyl ketone intermediate (26) were established unambiguously by X-ray crystallography.