24734-68-7

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

InChI:InChI=1/C9H12S/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,10H,4,7-8H2

Upstream product

• 30134-13-5 S-(3-phenylpropyl) ethanethioate 
• 122-97-4 3-Phenyl-1-propanol 
• 104-52-9 phenylpropyl chloride 
• 132150-34-6 3-phenylpropyl ethanethiolate 
• 114764-11-3 3-phenylpropyl 2-(trimethylsilyl)ethyl sulfide 
• 637-59-2 1-Bromo-3-phenylpropane 
• 105444-69-7 phenylpropyl carbamimidothioate hydrobromide 
• 114764-12-4 (3-Methyldisulfanyl-propyl)-benzene 
• 89987-96-2 1,2-bis(3-phenylpropyl)disulfane 
• 99168-03-3 dithiocarbamic acid-(3-phenyl-propyl ester) 

Downstream Products

• 30134-08-8 ((3-phenylpropyl)sulfanyl)acetic acid 
• 5755-57-7 2-(3-Phenyl-propylmercapto)-ethan-1-ol 
• 121041-58-5 6-(3'-phenylpropylthio)pyridazin-3-amine 
• 87119-51-5 (3-Phenylpropyl)-2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranosid 
• 101681-12-3 1-(3-phenylpropylsulfanyl)propan-2-one 
• 101681-11-2 3-diphenylphosphinoyloctan-2-one 
• 101681-02-1 (2RS,3SR,4SR,5SR)-5-diphenylphosphinoyl-4-(3-phenylpropylsulfanyl)decane-2,3-diol 
• 101681-03-2 (2S,3S,4R,5R)-5-(Diphenyl-phosphinoyl)-3-(3-phenyl-propylsulfanyl)-decane-2,4-diol 
• 109996-61-4 (2R,3S)-3-<(tert-butyloxycarbonyl)amino>-1-<(3-phenylpropyl)thio>-2-hydroxy-5-methylhexane 
• 104-52-9 phenylpropyl chloride 
• 78880-69-0 3-phenylpropane-1-sulphenyl chloride 
• 87598-28-5 1-Phenyl-2-(3-phenyl-propylsulfanyl)-ethanone 
• 38381-15-6 C₂₁H₂₈S₂ 
• 38381-11-2 C₂₁H₂₈S₂ 

Relevant academic research and scientific papers

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Photoisomerization of azobenzene-substituted alkanethiolates on Au(111) substrates in the context of work function variation: The effect of structure and packing density

Photoisomerization of a series of custom-designed, azobenzene-substituted alkanethiolate (AT) self-assembled monolayers (SAMs) on Au(111) substrates was studied in the context of work function variation, using Kelvin probe measurements as a transduction technique. These SAMs featured variable packing density (by ～14%; due to the odd-even effects) and, as an option, were additionally decorated with the electron donating/withdrawing -CH3 and -CF3 tail group, respectively, which induce additional dipole moments. The efficiency of photoisomerization and the respective extent of work function variation (ΔΦ) were found to be quite low and independent of the packing density in the SAMs, within the given odd-even packing density variation. They could only be increased, up to ca. 40 meV for ΔΦ, by mixing the azobenzene-substituted ATs with shorter "matrix" molecules, which were introduced for a partial release of the sterical constraints. The ΔΦ values for the SAMs decorated with the -CH3 and -CF3 tail groups were found to be lower than those for the monolayers without such a decoration, which correlated well with the theoretical estimates for the change of the dipole moment of the relevant molecules upon the photoisomerization.

Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles

A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl5-mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved.

Substrate and Catalyst Effects in the Enantioselective Copper-Catalysed C–H Insertion Reactions of α-Diazo-β-oxo Sulfones

Excellent enantioselectivities of up to 98 % ee are achieved by employing the copper-bis(oxazoline)-NaBARF catalyst system in the C–H insertion reactions of α-diazo-β-oxo sulfones. The influence of variation of the bis(oxazoline) ligand, copper salt, additive and substrate on both the efficiency and the enantioselectivities of these intramolecular C–H insertion reactions has been explored. Optimum enantioselectivities are achieved with phenyl and diphenyl ligands across the substrate series.

Two-step three-component process for one-pot synthesis of 8-alkylmercaptocaffeine derivatives

A highly efficient, odourless and two-step three-component process for one-pot synthesis of some 8-alkylmercaptocaffeine derivatives has been described. The catalyst-free three-component reaction of alkyl bromides, thiourea, and 8-bromocaffeine gave 8-alkylmercaptocaffeine products in excellent to quantitative yields. In addition, the impact of parameters on sample reaction is discussed.

A novel C-5′ substituted cinchona alkaloid-derived catalyst promotes additions of alkyl thiols to nitroolefins with excellent enantioselectivity

A new bifunctional C-5′ substituted cinchona alkaloid-based catalyst promotes the first highly enantioselective additions of alkyl thiols to nitrostyrenes. The Royal Society of Chemistry 2012.

Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues

In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 μM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl]caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 μM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.

Hydrophobic polymer-supported catalyst for organic reactions in water: Acid-catalyzed hydrolysis of thioesters and transprotection of thiols

(Matrix presented) A hydrophobic polystyrene-supported sulfonic acid was found to be effective for hydrolysis of thioesters in pure water. It was revealed that the catalyst was much superior to other Bronsted acid catalysts. Transprotection of thiols from thioesters to thioethers has been successfully performed in water using this catalytic system.

Cleavage of a p-cyanobenzyl group from protected alcohols, amines, and thiols using triethylgermyl sodium

Alcohols, amines, and thiols protected with a p-cyanobenzyl group can be easily and quantitatively deprotected using triethylgermyl sodium under mild conditions.

Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects

The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.