6007-26-7

Usage

Uses

Used in Chemical Synthesis:
2-METHYL-1,3-DITHIANE is used as a synthetic intermediate for the preparation of various organic compounds, particularly in the synthesis of methyl ketones. Its unique structure allows for selective reactions and the formation of desired products.
Used in the Preparation of Potassium Trifluoro(2-methyl-1,3-dithiano)borate:
2-METHYL-1,3-DITHIANE is used as a key component in the synthesis of potassium trifluoro(2-methyl-1,3-dithiano)borate. 2-METHYL-1,3-DITHIANE has potential applications in various chemical processes, including the formation of boron-containing compounds and as a reagent in organic reactions.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 6305, 1986 DOI: 10.1016/S0040-4039(00)87793-X

Purification Methods

Wash the dithiane with H2O, 2.5 M aqueous NaOH, H2O, brine, dry over K2CO3 (use toluene as solvent if the volume of reagent is small), filter, evaporate and distil the colourless residue. IR film: 1455, 1371 and 1060 (all medium and CH3), 1451m, 1422s, 1412m, 1275m, 1236m, max 1190m, 1171w, 918m and 866w (all dithiane) cm-1 [Corey & Erickson J Org Chem 36 3553 1971, Seebach & Corey J Org Chem 40 231 1975]. [Beilstein 19 III/IV 49, 19/1 V 53.]

InChI:InChI=1/C5H10S2/c1-5-6-3-2-4-7-5/h5H,2-4H2,1H3

Upstream product

• 109-80-8 1.3-propanedithiol 
• 75-07-0 acetaldehyde 
• 505-23-7 1,3 dithiane 
• 74-88-4 methyl iodide 
• 917-64-6 methyl magnesium iodide 
• 39915-66-7 1,3-dithian-2-yl tetrafluoroborate 
• 68984-53-2 1-(2-Methyl-1,3-dithian-2-yl)-1-phenyl-2-propen-1-ol 
• 13411-42-2 2-(trimethylsilyl)-1,3-dithiane 
• 18147-08-5 2,2-dimethyl-2-sila-1,3-dithiane 

Downstream Products

• 69824-31-3 {3-[1-(3-Methylsulfanyl-propylsulfanyl)-ethoxy]-propyl}-benzene 
• 69824-30-2 Benzoic acid 3-[1-(3-methylsulfanyl-propylsulfanyl)-ethoxy]-propyl ester 
• 69824-36-8 2-Methoxy-4-methyl-1-{(E)-4-[1-(3-methylsulfanyl-propylsulfanyl)-ethoxy]-but-2-enyloxy}-benzene 
• 7737-47-5 3-hydroxy-4,4-dimethylpentan-2-one 
• 37160-77-3 3-hydroxy-octan-2-one 
• 3155-01-9 3-hydroxy-3-phenyl-butan-2-one 
• 69824-28-8 [1-(3-Methylsulfanyl-propylsulfanyl)-ethoxy]-benzene 
• 167964-34-3 <4R,4(1R),5R,8S,9S>-4--2,2-dimethyl-6-oxo-9-<(trimethylsilyl)oxy>-1,3,7-trioxaspiro<4.4>nonan-8,9-dicarboxylic acid bis(phenylmethyl) ester 
• 167964-35-4 <4R,4(1S),5R,8S,9S>-9-Hydroxy-4--2,2-dimethyl-6-oxo-1,3,7-trioxaspiro<4.4>nonan-8,9-dicarboxylic acid bis(phenylmethyl) ester 
• 154047-37-7 (S)-1-(2-methyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-3-phenylpropane 
• 154047-38-8 (S)-1-(2-methyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-4-methylpentane 
• 78349-00-5 2-(4a-hydroxybenzyl)-2-methyl-1,3-dithiane 
• 177326-19-1 tert-Butyl-{(6R,7S)-6-methyl-7-[(R)-1-methyl-2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-1,4-dioxa-spiro[4.4]non-6-ylmethoxy}-diphenyl-silane 
• 1026222-70-7 3-[hydroxy-(2-methyl-[1,3]dithia-2-yl)-methyl]-benzonitrile 

Relevant academic research and scientific papers

Exploiting the 1,3-dithiane of 2-oxopropanenitrile oxide to limit competing dimerization in 1,3-dipolar cycloaddition reactions

The 1,3-dithiane of 2-oxopropanenitrile oxide is less prone to dimerization than the parent compound and, as a consequence, it undergoes more efficient cycloaddition reactions with a range of mono- and 1,1- and 1,2-di-substituted alkenes.

Stable isotope13 C mark of the pyruvic acid preparation method (by machine translation)

The invention relates to stable isotope13 C mark of the pyruvic acid preparation method, the use of13 C mark acetaldehyde as raw material, with the thioalcohol condensation to obtain the13 C mark sulfur acetal intermediate, with butyl lithium reaction to obtain the intermediate13 C mark dithioacetal alkyl lithium solution, then with13 CO2 Reaction intermediates13 C mark II sulfur [...], final deprotection of the final product is obtained13 C mark pyruvic acid. This invention to the cheap and easy stable isotope raw material, using a novel synthetic method, a brief four-step synthetic route, mild reaction conditions, has been seven13 C mark pyruvic acid product, its chemical purity higher than 99%, abundance are higher than the 99% atom13 C, impurity content in accordance with the Pharmacopoeia requirement, can fully meet the MRI used for the clinical diagnosis of tumor imaging drug, and has good economy and use value. (by machine translation)

2,3,5-Trisubstituted pyridines as selective AKT inhibitors. Part II: Improved drug-like properties and kinase selectivity from azaindazoles

A novel series of AKT inhibitors containing 2,3,5-trisubstituted pyridines with novel azaindazoles as hinge binding elements are described. Among these, the 4,7-diazaindazole compound 2c has improved drug-like properties and kinase selectivity than those of indazole 1, and displays greater than 80% inhibition of GSK3β phosphorylation in a BT474 tumor xenograft model in mice.

Pyrazine biosynthesis in corynebacterium glutamicum

The volatile compounds released by Corynebacterium glutamicum were collected by use of the CLSA technique (closed-loop stripping apparatus) and analysed by GC-MS. The headspace extracts contained several acyloins and pyrazines that were identified by their synthesis or comparison to commercial standards. Feeding experiments with [2H7]acetoin resulted in the incorporation of labelling into trimethylpyrazine and tetramethylpyrazine. Several deletion mutants targeting genes of the primary metabolism, were constructed to elucidate the biosynthetic pathway to pyrazines in detail. A deletion mutant of the ketol-acid reductoisomerase was not able to convert the acetoin precursor (S)2-acetolactate into the pathway intermediate (R)-2,3-dihydroxy-3-methylbutanoate to the branched amino acids. This mutant requires valine, leucine, and isoleucine for growth and produces significantly higher amounts and more different compounds of the acyloin and pyrazine classes. Gene deletion of the acetolactate synthase (AS) resulted in a mutant that is not able to convert pyruvate into (5)-2-acetolactate. This mutant also requires branched amino acids and produces only very small amounts of pyrazines likely from valine via the valine biosynthetic pathway operating in reverse order. A ΔASΔKR double mutant was constructed that does not produce any pyrazines at all. These results open up a detailed biosynthetic model for the formation of alkylated pyrazines via acyloins.

Externally sensitized mesolytic fragmentations in dithiane-ketone adducts

The apparent activation enthalpies, ΔH≠, for externally sensitized mesolytic fragmentations in benzophenone-dithiane adducts were obtained in variable temperature photolyses and compared with DFT activation barriers calculated for β-scission in the corresponding oxygen-centered radicals. The results of these experimental and theoretical studies further support the mechanism in which deprotonation of the hydroxy-group, in the transient cation radical, is coupled with intramolecular electron transfer furnishing the O-centered radical, which subsequently fragments. The quantum yields of fragmentation increase for higher alkyl substituted dithiane adducts.

Enzyme assisted syntheses of chiral building blocks for isosters of diglycerides, phospholipids and PAF

Lipase catalyzed desymmetrizations of suitably substituted, achiral 1,3-diols lead to the corresponding chiral building blocks of high enantiomeric purities, starting materials for the synthesis of isosteric carba-analogues of 1,2-sn-diglycerides and phospholipids with interesting biological activities. Lipase catalyzed resolutions of the corresponding ether derivatives lead to the corresponding building blocks for carba-analogues of PAF.

Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of α-aminoacids

Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two α-hydrazido carboxylic acids, well-known precursors of α-amino acids. (C) 2000 Elsevier Science Ltd.

Aggregative activation and carbanion chemistry: Complex base deprotonation and directed functionalisation of dithioacetals

Bis(phenylthio)methane and [1,3]-dithiane were efficiently deprotonated by the NaNH2-Et(OCH2CH2)2-ONa complex base. A marked behaviour difference was observed between the sodium carbanion of [1,3]-dithiane and the corresponding lithio-derivative. A 'radicaloid' mechanism is proposed to explain the results observed.

Solution ion pair structure of 2-lithio-1,3-dithianes in THF and THF-HMPA

An NMR study of 2-lithio-1,3-dithiane and 2-triorganosilyl-, 2-tert-butyl- and 2-phenyl-2-lithiodithianes reveals that all are contact ion pair species in THF and all become separated ions with excess HMPA. The dithianes differ greatly in their ease of ion separation, with the parent lithiodithiane the most difficult.

A RAPID, EFFICIENT AND SELECTIVE CONVERSION OF ALDEHYDES AND ACETALS TO THEIR 1,3-DITHIANE DERIVATIVES WITH 2,2-DIMETHYL-2-SILA-1,3-DITHIANE1

Aldehydes and acetals are cleanly and rapidly converted to the corresponding dithianes with 2,2-dimethyl-2-sila-1,3-dithiane and stochiometric amounts of boron trifluoride etherate even in the presence of ketones, which do not react competitively with the reagent.