85387-90-2

Upstream product

• 59277-53-1 (E)-3-(ethylthio)-1-phenylpropene 
• 4392-24-9 Cinnamyl bromide 
• 594-44-5 Ethanesulfonyl chloride 
• 598-59-4 ethylsulfinic acid 
• 104-54-1 3-Phenylpropenol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 141811-44-1 2-(ethanesulfonyl)acetic acid 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 85387-91-3 6-Ethylsulphonyl-5-hydroxy-8-phenyl-7-octenoic acid, sodium salt 

Relevant academic research and scientific papers

Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

The photooxygenation of benzyl, heteroarylmethyl, and allyl sulfides

The photosensitised oxidation of benzyl ethyl sulfides in aprotic solvents (benzene or acetonitrile) gives the corresponding aldehydes under mild conditions. This is a general reaction which applies to benzyl derivatives containing either electron-donating or electron-withdrawing substituents and furthermore to hereto analogues such as 2-pyridinylmethyl sulfide (not to the 3-indolylmethyl sulfide, since reaction at the heterocycle moiety competes) as well as to allyl sulfides. In a protic solvent (methanol) these sulfides give the sulfoxides instead (except for the nitrobenzyl derivatives, where the aldehyde remains the major product). Among the α-substituted sulfides tested, the α-phenylbenzyl and the 3- cyclohexenyl sulfide give the corresponding ketone (the latter in a low yield), but the α-methylbenzyl sulfide gives the sulfoxide as the main product. The rate for singlet oxygen quenching and for chemical reaction have been measured for representative benzyl sulfides. The reaction is discussed in the frame of the currently accepted mechanism for sulfide photooxygenation. The key step for oxidative C-S bond cleavage appears to be hydrogen transfer from the activated α position in the first formed intermediate, the persulfoxide. This reaction is inhibited in methanol where the persulfoxide is hydrogen-bonded.

A convenient method for the synthesis of β,γ-unsaturated sulfones through zinc-mediated C-S coupling reaction

Through zinc-mediated coupling reaction of allylic bromides with alkane- or arenesulfonyl chlorides, β,γ-unsaturated sulfones were obtained with moderate to good yields.

SRS-A antagonists

There are described pharmacologically active compounds, useful in the treatment of allergic/inflammatory disorders involving SRS-A as causal mediator and which, in free acid form, are of formula I, STR1 in which R1 is (i) an aliphatic, saturated or unsaturated hydrocarbyl radical of up to 20 carbon atoms, unsubstituted or substituted by at least one substituent selected from halogen, hydroxy, C3-6 alkoxy, C3-6 cycloalkyl, aryl or heteroaryl, the cycloalkyl, aryl or heteroaryl being unsubstituted or substituted by at least one substituent selected from hydroxy, halogen and alkyl, alkenyl or alkynyl of up to 10 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms unsubstituted or substituted by alkyl, alkenyl or alkynyl of up to 16 carbon atoms, or (iii) aryl or heteroaryl, unsubstituted or substituted by hydroxyl, C1-4 alkoxy, halogen or alkyl, alkenyl or alkynyl of up to 16 carbon atoms; and R2 is (i) alkyl, cycloalkyl or alkenyl of up to 10 carbon atoms, unsubstituted or substituted by one or more substituents selected from aryl, cycloalkyl, halogen, hydroxy, NHR3 and COX, where R3 is H, C1-4 alkyl, aryl or an amino acid residue or COX, and X is OH, C1-4 alkyl, NH2 or an amino acid residue, or (ii) aryl or heteroaryl, unsubstituted or substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, C2-5 acyl, halogen, hydroxy, carboxy, nitro, trihalomethyl, phenyl, C1-4 acylamino and NHR4, where R4 is hydrogen or C1-4 alkyl; and Y is --S--, --SO-- or --SO2 --, with the proviso that when --YR2 is glutathionyl, cysteinyl or cysteinylglycinyl, then R1 is other than an unsubstituted alkatetraenyl or alkapentaenyl radical of 12 to 16 carbon atoms.