53138-46-8

Basic information

• Product Name: (+/-)-cis,trans-4-methyl-2-phenylsulfanylbutyrolactone
• Synonyms: (+/-)-cis,trans-4-methyl-2-phenylsulfanylbutyrolactone
• CAS NO: 53138-46-8
• Molecular Weight: 208.281
• Mol File: 53138-46-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (+/-)-cis,trans-4-methyl-2-phenylsulfanylbutyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-cis,trans-4-methyl-2-phenylsulfanylbutyrolactone(53138-46-8)
• EPA Substance Registry System: (+/-)-cis,trans-4-methyl-2-phenylsulfanylbutyrolactone(53138-46-8)

Safety Data

• Hazardous Substances Data: 53138-46-8(Hazardous Substances Data)

Upstream product

• 84796-82-7 methyl 4-oxo-2-(phenylthio)pentanoate 
• 84796-81-6 4-Oxo-2-phenylsulfanyl-pentanoic acid 
• 70982-76-2 3-hydroxy-2-phenylthiopentanoic acid 
• 103-04-8 (phenylthio)acetic acid 
• 882-33-7 diphenyldisulfane 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 25966-39-6 3-bromo-5-methyldihydrofuran-2(3H)-one 
• 930-69-8 sodium thiophenolate 
• 115367-77-6 4-Ethyl-3-phenylsulfanyl-oxetan-2-one 
• 90670-14-7 4-Hydroxy-2-phenylsulfanyl-pentanoic acid methyl ester 

Downstream Products

• 92611-88-6 2-hydroxy-5-methyl-3-phenylthio-2-<4-<(tetrahydropyran-2-yl)oxy>butyl>tetrahydrofuran 
• 591-11-7 5-methyl-5H-furan-2-one 
• 53138-50-4 (+/-)-cis,trans-4-methyl-2-phenylsulfinylbutyrolactone 
• 75280-22-7 Acetic acid 5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl ester 
• 219719-04-7 (+/-)-cis,trans-2-chloro-4-methyl-2-phenylsulfanylbutyrolactone 
• 1160526-79-3 C₂₀H₂₂O₃S 
• 92611-59-1 (2S,4R,5R)-4-Benzenesulfinyl-2-methyl-1,6-dioxa-spiro[4.5]decane 
• 92611-59-1 (2R,4R,5R)-4-Benzenesulfinyl-2-methyl-1,6-dioxa-spiro[4.5]decane 
• 92611-89-7 2-[4-((S)-5-Methyl-3-phenylsulfanyl-4,5-dihydro-furan-2-yl)-butoxy]-tetrahydro-pyran 
• 92611-59-1 (2R^*,4S^*,5S^*,S^*_S)-2-methyl-4-phenylsulfinyl-1,6-dioxaspiro<4.5>decane 
• 92611-59-1 (2R^*,4R^*,5R^*,R^*_S)-2-methyl-4-phenylsulfinyl-1,6-dioxaspiro<4.5>decane 
• 92611-59-1 (2R^*,4S^*,5S^*,R^*_S)-2-methyl-4-phenylsulfinyl-1,6-dioxaspiro<4.5>decane 
• 92611-59-1 (2R^*,4R^*,5R^*,S^*_S)-2-methyl-4-phenylsulfinyl-1,6-dioxaspiro<4.5>decane 
• 92611-59-1 (2R^*,4R^*,5S^*,S^*_S)-2-methyl-4-phenylsulfinyl-1,6-dioxaspiro<4.5>decane 

Relevant articles and documents

Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity

The synthesis of 5- and 3-(1′-hydroxyalkyl)-substituted 5H-furan-2-ones 4a-d and 8a-d as well as 5-alkylidene-5H-furan-2-ones 5a-d is described. A study of the structure-activity relationship of these furanone-based natural product analogues towards two different quorum sensing systems is reported. Although the synthesized compounds are not as potent quorum sensing inhibitors as some natural counterparts and a synthetic analogue hereof, interesting structure-activity relationships are seen.

Stannylfuranones in synthesis: Highly enantioselective preparation of (+)-hamabiwalactone B

An unambiguous and highly enantioselective total synthesis of the naturally-occurring 2(5H)-furanone hamabiwalactone B has been achieved. The key step is a Stille coupling of novel stannylfuranone 2 with (E)-iodoalkene 3. The enantiomeric purity of the synthetic natural product was ≥ 99%, as judged by chiral HPLC.

Michael Reaction of Conjugated Nitro Olefins with Carboxylic Acid Dianions and with Ester Enolates: New Synthesis of γ-Keto Acids and γ-Keto Esters

Base-sensitive conjugated nitro olefins 2 reacted with lithium dianions of carboxylic acids 3 or with lithium enolates of esters 4 at a low temperature of ca. -100 deg C, and subsequent treatment of the Michael adducts with aqueous acid yielded γ-keto acids 5 or esters 5' in a one-pot operation, respectively.Results of both the reactions have been compared.Some applications of the resulting γ-keto esters in organic synthesis have also been demonstrated in lactone synthesis and cyclenone annulation.