37850-75-2

Usage

Chemical compound

Allyl sec-butyl sulfide

Source

Commonly found in Allium species such as garlic, onions, and shallots

Odor and taste

Responsible for the pungent odor and taste associated with garlic, onions, and shallots

Health benefits

Studied for potential anti-inflammatory, antioxidant, and anticancer properties

Research interest

Compound of interest for further research in the fields of medicine and food science

InChI:InChI=1/C7H14S/c1-4-6-8-7(3)5-2/h4,7H,1,5-6H2,2-3H3

Upstream product

• 75-66-1 2-methylpropan-2-thiol 
• 106-95-6 allyl bromide 
• 61865-96-1 (Z)-t-butyl 1-propenyl sulfide 
• 64955-40-4 2-acetoxy-1-tert-butylsulfanyl-propane 
• 61866-00-0 (E)-t-butyl 1-propenyl sulfide 
• 107-05-1 3-chloroprop-1-ene 
• 513-44-0 2-methylpropanethiol-1 
• 29364-29-2 sodium tert-butyl thiolate 
• 870-23-5 prop-2-ene-1-thiol 
• 507-19-7 t-butyl bromide 
• 127699-25-6 Diallyl selenide 
• 107-18-6 allyl alcohol 
• 110-06-5 di-tert-butyl disulfide 

Downstream Products

• 89795-31-3 t-Butyl-propenyl-sulfid 
• 926-40-9 2-methyl-2-propylsulfanyl-propane 
• 61866-00-0 (E)-t-butyl 1-propenyl sulfide 
• 24367-44-0 2-(2-tert-butyldisulfanyl)pyridine 
• 112-88-9 octadec-1-ene 
• 89025-53-6 n-pentadecyl-2'-pyridylsulphide 
• 110890-30-7 1-t-butylthio-3-triphenylsilyl-1-propene 
• 97250-57-2 1-allyl-1-methylcyclododecane 
• 107183-92-6 N-(propen-3' yl) N-tosyl dimethyl-1,1 ethanesulfenamide 
• 61865-96-1 (Z)-t-butyl 1-propenyl sulfide 
• 118217-76-8 1,3-Dibromo-2-tert-butylsulfanyl-propane 
• 78286-74-5 (2-tert-Butylsulfanyl-1-methyl-ethyl)-phenyl-amine 
• 78286-75-6 (2-tert-Butylsulfanyl-1-methyl-ethyl)-methyl-phenyl-amine 
• 83877-55-8 (E)-4-tert-Butylsulfanyl-1-cyclohexyl-but-3-en-1-ol 

Relevant academic research and scientific papers

A non-calcemic sulfone version of the vitamin D3 analogue seocalcitol (EB 1089): chemical synthesis, biological evaluation and potency enhancement of the anticancer drug adriamycin

Novel side-chain diene sulfones 5, analogues of the natural hormone 1α 25-dihydroxyvitamin D3 (calcitriol, 1), were designed to incorporate some of the therapeutically most favorable structural features of the Leo Pharmaceutical Companys drug candidate diene EB 1089 (seocalcitol, 4) and of the Hopkins' non-calcemic side-chain sulfone analogues 2 and 3. Synthesis of diene sulfones 5 features selective Swern oxidation of a primary silyl ether in the presence of a secondary silyl ether (9→10) and Horner Wadsworth Emmons aldehyde addition by a 1-phosphonyl-3-sulfonyl stabilized carbanion regiospecifically at the 1-position to form E,E-diene sulfone 11. Sulfone diene analogue 5a with natural 1α,3b-diol functionality, but not its diastereomer 5b with unnatural A-ring stereochemistry, is antiproliferative in vitro toward murine keratinocytes and malignant melanoma cells, as well as toward MCF-7 human breast cancer cells. Combining diene sulfone 5a with the currently used anticancer drug adriamycin (ADR) caused a noteworthy 3-fold enhancement of ADR antiproliferative potency in MCF-7 cells. Sulfone diene analogue 5a is weakly active transcriptionally in MCF-7 and ROS 17/2.8 cells, binds poorly but measurably to the vitamin D receptor (VDR), and desirably is non-calcemic in vivo at a daily dose (7 days) of 10 mg/kg of rat body weight. Copyright

Preparation of Functionalized α,β-Unsaturated Sulfonamides via Olefin Cross-Metathesis

The synthesis of functionalized α,β-unsaturated sulfonamides by means of cross-metathesis of vinyl sulfonamides and olefins has been developed. The reaction proceeds smoothly in the presence of Hoveyda-Grubbs catalyst and its nitro analogue, providing a w

Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects

A case study on the polarity effects of radical mediated intermolecular alkene aminoallylation is presented herein. This radical group transfer method pairs vinyl ethers with electronically deficient allyl-oxyphthalimide derivatives to give difunctionalized products while illustrating the guiding effects of polarity on this radical reactivity.

Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates

The allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with either a Ru Iv catalyst, [Ru(Cp*)(n3CH5)(CH 3CN)2](PF6)2 (2; Cp* = pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH 3CN)3](PF6) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH3CN) 3](PF6) alone affords poor results. A comparison is made to the results from catalytic runs based on the use of carbonates rather than alcohols, by using 2 as the catalyst, and it is shown that the products from the alcohols are formed faster, so there is no advantage in using a carbonate substrate. The observed branched-to-linear (b/1) ratios when using substituted alcohols decrease with time suggesting that the catalysts isomerise the products. A new methodology from which one can select the desired isomeric product is proposed. DFT calculations and NMR spectroscopic measurements, by using an arene sulfonic acid as co-catalyst, suggest that 6-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that l)any rf-complexes from the acids RC6H4SO 3H result from deprotonation of the acid, 2) complexation of the thiol, via the deprotonated sulfur atom, is preferred over complexation of the O atom of the sulfonate, RC6H4SO3and 3) a sulfonate O-atom complex will be difficult to detect.

Preparation of thioethers using SN1-active halides and zinc mercaptides

SN1-Active (tertiary alkyl, allylic and benzylic) halides react with zinc mercaptides, prepared in situ by contacting mercaptans with either zinc carbonate or zinc sulphide, under optimised conditions, to afford thioethers in moderate to very good yields (50-95 percent). The method is particularly useful for the preparation of thioethers with at least one bulky alkyl group.

Synthesis and use of amino acid fluorides as peptide coupling reagents

The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: STR1 or the acid fluoride salts thereof wherein BLK is an N-amino protecting group AA is an amino acid residue and X is H or a protecting group useful, and the first amino and peptide have a free amino group and a blocked carboxy end.

Low pressure hydrogenation of unsaturated sulphides with homogeneous and heterogeneous ruthenium catalysts

Ru2O·nH2O and [Ru3O(AcO)6(H2O)3]+AcO- were examined for catalytic activity in the hydrogenation of a series of unsaturated sulphides under heterogeneous and homogeneous conditions, respectively. By the appropriate combination of these two methodologies, a number of saturated sulphides could be synthesized in satisfactory to good yields, thus minimizing side reactions.

Asymmetric hydroformylations of sulfur-containing olefins catalyzed by BINAPHOS-Rh(I) complexes

Asymmetric hydroformylations of vinyl sulfides, allyl sulfides, and allyl sulfones catalyzed by (R,S)-BINAPHOS/Rh(acac)(CO2) afforded the corresponding branched oxo aldehydes as major products in 60-80% ee. Use of bulkier substituents on the sulfur in vinyl sulfides gave the branched oxo-aldehydes in higher regio- and enantioselectivities.

Synthesis and use of amino acid fluorides as peptide coupling reagents

A compound of the formula STR1 or the acid fluoride salts thereof wherein BLK is an N-amino protecting group or hydrogenAA is an amino acid residue andX is H or a protecting group useful as a coupling agent in peptide synthesis.