104281-52-9

Upstream product

• 502-72-7 cyclopentadecanone 
• 931-59-9 benzenesulfenyl chloride 
• 104281-50-7 1-trimethylsiloxycyclopentadecene 
• 60447-89-4 2-bromocyclopentadecan-1-one 
• 108-98-5 thiophenol 

Downstream Products

• 145286-03-9 E-1-Methyl-15-phenylthiocyclopentadec-1-ene 
• 104281-71-2 2-Phenylthiomethylenecyclopentadecane 
• 63975-98-4 (S)-muscone 
• 104281-63-2 anti-2-Methyl-2-phenylthiocyclopentadecanol 
• 104281-63-2 syn-2-Methyl-2-phenylthiocyclopentadecanol 
• 104281-56-3 2-Methyl-2-phenylthiocyclopentadecanone 
• 63615-17-8 2-(phenylsulfinyl)cyclopentadecanone 

Relevant academic research and scientific papers

Asymmetric Synthesis of (R)-(-)- and (S)-(+)-Muscone by Enantioselective Conjugate Addition of Chiral Dimethylcuprate to (E)-Cyclopentadec-2-en-1-one

A variety of optically active secondary amino alcohols have been prepared from camphor and screened as chiral non-transferable cuprate ligands in conjugate addition reactions.The reactions of (E)-cyclopentadec-2-en-1-one with chiral dimethylcuprates derived from the ligand in toluene afforded muscone in enantiomeric excesses as high as 26 - 89 percent.The stereochemistry of the product correlates with the configuration of the chiral ligand used.Thus the conjugate addition using the ligand prepared from exo-3-monosubstituted-amino-exo-2-hydroxybornane gave (S)-(+)-muscone, while with endo-ligand, (R)-(-)-muscone was obtained in higher enantioselectivity.Muscone of essentially 100percent optical purity was obtained by the addition of small amounts of THF (tetrahydrofuran) (2 - 10 equiv.) to the toluene solution of the chiral cuprate reagent prepared from (1R,2R,3S,4S)-3--1,7,7-trimethylbicycloheptan-2-ol 23 (endo-MPATH).The effect of the stoichiometry of the chiral ligand and the cuprate reagent on the chemical yield and enantioselectivity was briefly investigated.

Synthesis of Cyclic Allylic Sulphides (Ring Sizes 5-15) via Phenylthio Participation

Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it.Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic su

REARRANGEMENT OF CYCLIC ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS-) GROUP: MIGRATION OF A PhS GROUP AROUND A RING.

PhS migratoin around rings (size 5-15) gives allyl sulphides with a regioselectivity wich varies with ring size.