5925-74-6

Usage

InChI:InChI=1/C12H18N2O/c1-10-4-6-11(7-5-10)12(15)13-8-9-14(2)3/h4-7H,8-9H2,1-3H3,(H,13,15)

Upstream product

• 15081-75-1 3,3-Bis-methylthio-1,2-diphenyl-prop-2-enol 
• 14063-69-5 β,β-bis(methylthio)styrene 
• 74-93-1 methylthiol 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 7714-33-2 methyl phenylethynyl sulfide 
• 64759-73-5 1,1-bis(methylthio)-2-chloro-2-phenylethylene 
• 35453-05-5 methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane 
• 83994-44-9 trimethyl orthoselenophenylacetate 
• 88738-26-5 (E)-1-methoxy-2-phenyl-1-(phenylthio)ethene 
• 35638-70-1 lithium methanethiolate 
• 5418-86-0 tris(methylthio)methane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 3389-53-5 phenylacetylpyrrolidine 
• 144043-54-9 S-methyl phenyldiazothioacetate 

Relevant academic research and scientific papers

Acid-Catalyzed Hydrolysis of a Phenylketene Dithioacetal. Reversible Protonation of the Carbon-Carbon Double Bond

Reactions of 1,1-bis(methylthio)-2-phenylethene (1) were followed in acidic CD3CN-D2O (50-90 vol percent) solutions by 1H NMR spectroscopy.The H-D isotope exchange at the 2-position (to give 2-deuterio derivative 1-d) occurs concurrently with hydrolysis, which gives S-methyl phenylthioacetate.Relative rates of the isotope exchange to the hydrolysis increase from 1.0 to 13.4 on going from 50 to 90 vol percent content of CD3CN.Rates of the hydrolysis were also measured by UV spectroscopy in 10 vol percent CH3CN-H2O (D2O) at 30 deg C.Pseudo-first-order plots for the reaction of 1 in CH3CN-D2O curved as expected from the concurrent isotope exchange, the relative rate of exchange to hydrolysis being 2.1 in this medium.The deuterated substrate 1-d is about 1.4 times as reactive as 1; this large apparent secondary kinetic isotope effect is ascribed mainly to the reduced reversibility of protonation of 1-d rather than to true secondary effects.The hydrolysis rate increases rapidly with increasing buffer concentration to reach a constant maximum value at about 30percent increase.Added 2-mercaptoethanol accelerates the disappearance of 1.All the results are accommodated by a mechanism involving a largely reversible protonation of the double bond and a mostly rate-determining hydration of the carbocation intermediate.

Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade

Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as 5-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38). The Royal Society of Chemistry 2010.

A Fast and Solvent-Free Conversion of Thioamides into Thioesters

Solvent-free irradiation of thiomorpholides with two kinds of methylating agents under microwave or ultrasonic conditions gave the corresponding thioesters in high yield. The method is simple and avoids prolonged heating with solvents.

Synthesis of chalcogenol esters from chalcogenoacetylenes

Thiol and selenol esters were conveniently prepared in good yields by reacting chalcogenoacetylenes with trifluoroacetic acid in dichloromethane in the presence of silica.

S,S-dimethyl dithiocarbonate: A novel carbonyl dication synthon in the synthesis of ketones

We report herein the use of DMDTC as an effective carbonyl dication equivalent in ketone synthesis. According to our strategy, we also successfully devised a synthetic pathway for S-methyl (trimethylsilyl)thioacetate which may be a potentially useful synthetic reagent in organic synthesis.

Synthesis of thiolesters from thioacetylenes

Thiolesters were conveniently prepared in good yields by reacting thioacetylenes with p-toluenesulfonic or trifluoracetic acid in dichloromethane in the presence of silica.

A Horner-Wittig approach of S,N-ketene acetals. Acid-catalyzed hydrolysis of S,N-ketene acetals to (S)-thioesters

The synthesis of S,N-acetals of formyldiphenylphosphine oxide 2 is described. The stable lithiated anions of these acetals were applied in a Horner-Wittig reaction with several structural types of aldehydes. The resulting S,N-ketene acetals 1 were obtaine

ARYL THIOPYRANO[2,3,4-C,D]INDOLES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS

Compounds having the formula I: are inhibitors of 5-lipoxygenase and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cyto-protective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

Synthetic Application of Lithiated Tris(methylthio)methane: Preparation of Aliphatic Methyl Thiolcarboxylates from the Corresponding Halides. Convenient Synthesis of Tris(methylthio)methane

A thorough study directed towards the synthesis of methyl thiolcarboxylates was made on the basis of the following steps: (i) conversion of alkyl halides into the corresponding trimethyl trithioorthocarboxylates by using tris(methylthio)methyllithium in THF at -78 degC; (ii) selective hydrolysis of the intermediates to methyl thiolcarboxylates by using 35percent aq.HBF4 in DMSO or, in some cases, in THF.The overall yields of the two stages are, usually, between 70 and 88percent.By this procedure it is also possible to incorporate 18O in the carbonyl group of thiol esters (ca. 98percent isotopic purity).Furthermore, a new, convenient method for the preparation of tris(methylthio)methane as the precursor of tris(methylthio)methyllithium was developed.

Flash Photolytic Generation and Reactivity of Phenyl(methylthio)ketene in Aqueous Solution

Methyl phenyldiazothioacetate is found to undergo Wolff rearrangement to phenyl(methylthio)ketene upon flash photolysis in aqueous solution and not to add water forming an ester enol as is the case with its oxygen analog, methyl phenyldiazoacetate.Hydrati