17482-19-8

Usage

InChI:InChI=1/C11H14O2S/c1-3-4-9-14(12,13)11-7-5-10(2)6-8-11/h3,5-8H,1,4,9H2,2H3

Upstream product

• 17482-16-5 but-1-en-4-yl p-tolyl sulfide 
• 5162-44-7 1-bromo-4-butene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 624-31-7 4-tolyl iodide 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 10486-08-5 sodium p-thiocresolate 

Downstream Products

• 138842-48-5 methyl 2-methyl-4-(p-tolylsulfonyl)butanoate 
• 138842-51-0 dimethyl 2-<2-(p-tolylsulfonyl)ethyl>succinate 
• 135579-12-3 N-(but-3-enyl)-N-phenylacetamide 
• 1260118-93-1 1-(4-(4-tosylbutan-2-yl)phenyl)ethanone 
• 1260118-92-0 1-(4-(4-tosylbutyl)phenyl)ethanone 
• 86537-30-6 1-(p-tolylsulfonyl)bicyclo<1.1.0>butane 
• 412346-68-0 2-(2-tosylethyl)oxirane 
• 775318-21-3 N-(but-3-enyl)-N-(p-phenoxyphenyl)acetamide 

Relevant academic research and scientific papers

Multicomponent Reductive Cross-Coupling of an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Diversely Functionalized Sulfones

Conventionally, sulfones are prepared by oxidation of sulfides with strong oxidants. Now, a multicomponent reductive cross-coupling involving an inorganic salt (sodium metabisulfite) for the straightforward construction of sulfones is disclosed. Both intramolecular and intermolecular reductive cross-couplings were comprehensively explored, and diverse sulfones were accessible from the corresponding alkyl and aryl halides. Intramolecular cyclic sulfones were systematically obtained from five- to twelve-membered rings. Naturally occurring aliphatic systems, such as steroids, saccharides, and amino acids, were highly compatible with the SO2-insertion reductive cross-coupling. Four clinically applied drug molecules, which include multiple heteroatoms and functional groups with active hydrogens, were successfully prepared via a late-stage SO2 insertion. Mechanistic studies show that alkyl radicals and sulfonyl radicals were both involved as intermediates in this transformation.

Aryl alkyl sulfone compound and reducing coupling method for constructing sulfone compounds

The invention discloses an aryl alkyl sulfone compound shown as a formula (1) and a synthetic method thereof. The aryl alkyl sulfone compound is prepared by taking an aromatic iodide, an inorganic sulfur reagent and an alkyl bromide as reaction raw materials to carry out reacting in a solvent under action of alkali, a catalyst, a ligand, a reducing agent and an additive. According to the invention, an inorganic sulfur reagent is used as a sulfur source to construct the aryl alkyl sulfone compound in one step under catalysis and reduction conditions, so that the defect in synthesizing the arylalkyl sulfone compound by conventional oxidation of thioether is avoided. The aryl alkyl sulfone compound developed by the invention can be used for synthesizing aryl alkyl sulfone medicines.

DISULFIDE BIOCONJUGATION

Compounds and methods are provided for one-step functionalization of disulfide bonds in proteins.

Synthesis of arylethyl (E)-styrylsulfones and arylsulfones by one-pot DIBAL-H/NaH-mediated reaction of β-ketosulfones

A facile one-pot synthetic route for preparing a series of arylethyl (E)-styrylsulfones or arylethyl arylsulfones is developed. The efficient one-pot DIBAL-H/NaH-mediated route includes reduction of α-benzyl-β- arylketosulfones and retroaldol/aldol or retro aldol reaction of the resulting intermediate. The DIBAL-H/NaH-mediated reaction mechanism has been discussed. Georg Thieme Verlag Stuttgart. New York.

Hydride affinities of cumulated, isolated, and conjugated dienes in acetonitrile

(Chemical Equation Presented) The hydride affinities (defined as the enthalpy changes in this work) of 15 polarized dienes [five phenyl sulfone substituted allenes (1a), the corresponding five isolated dienes (1b), and the corresponding five conjugated dienes (1c)] in acetonitrile solution were determined by titration calorimetry for the first time. The results display that the hydride affinity scales of the 15 dienes in acetonitrile range from -71.6 to -73.9 kcal/mol for 1a, from -46.2 to -49.7 kcal/mol for 1b, and from -45.0 to -46.5 kcal/mol for 1c, which indicates that the hydride-obtaining abilities of the cumulated dienes (1a) are not only much larger than those of the corresponding conjugated dienes (1c) but also much larger than those of the corresponding isolated dienes (1b). The hydrogen affinities of the 15 dienes as well as the hydrogen affinities and the proton affinities of the radical anions of the dienes (1-.) in acetonitrile were also evaluated by using relative thermodynamic cycles according to Hess's law. The results show that (i) the hydrogen affinities of the neutral dienes 1 cover a range from -44.5 to -45.6 kcal/mol for 1a, from -20.4 to -21.4 kcal/ mol for 1b, and from -17.3 to -18.5 kcal/mol for 1c; (ii) the hydrogen affinities of the radical anions of the dienes (1-.) in acetonitrile cover a range from -40.6 to -47.2 kcal/mol for 1a-., from -21.6 to -29.6 kcal/mol for 1b-., and from -10.0 to -15.4 kcal/mol for 1c-.; (iii) the proton affinities of the 15 1a-. in acetonitrile cover a range from -97.0 to -100.6 kcal/mol for 1a-., from -77.8 to -83.4 kcal/ mol for 1b -., and from -66.2 to -68.9 kcal/mol for 1c-.. The main reasons for the great difference between the cumulated dienes and the corresponding isolated and conjugated dienes in the hydride affinity, hydrogen affinity, and proton affinity have been examined. It is evident that these experimental results should be quite valuable to facilitate the elucidation of the origins of the especially high chemical potencies of the allenes, the choice of suitable hydride reducing agents to reduce the dienes, and the analyses on the reduction mechanisms.