5718-75-2

Usage

Uses

Used in Fragrance and Flavor Industries:
Thiocineole is used as a key ingredient in the fragrance and flavor industries for its unique and strong scent, which adds depth and complexity to various products.
Used in Pharmaceutical Products:
In the pharmaceutical industry, thiocineole is used as an active ingredient for its antifungal and antimicrobial properties, contributing to the development of treatments for various infections.
Used in Personal Care Products:
Thiocineole is utilized in personal care products due to its antimicrobial properties, which help maintain hygiene and prevent the growth of harmful microorganisms on the skin and hair.
Used in Respiratory Condition Treatments:
Although research is ongoing, thiocineole is being studied for its potential therapeutic effects on respiratory conditions such as asthma and bronchitis, possibly offering relief through its unique chemical properties.

InChI:InChI=1/C10H18S/c1-7-4-5-8-6-9(7)11-10(8,2)3/h7-9H,4-6H2,1-3H3

Upstream product

• 10482-56-1 (-)-(S)-α-terpineol 
• 83150-77-0 C₁₀H₁₈S 
• 80-26-2 terpinyl acetate 
• 138-86-3 limonene. 
• 5989-27-5 D-limonene 
• 1208985-44-7 (1R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene 

Downstream Products

• 1678-82-6 trans-1,4-menthane 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 5989-27-5 D-limonene 
• 1195-31-9 (+)-p-menth-1-ene 
• 1269141-77-6 (1R,4R,5R,6R)-6-benzyl-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octan-6-ium trifluoromethanesulfonate 
• 1448809-33-3 4-((((1R,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl)thio)methyl)benzonitrile 
• 1269141-84-5 (1R,4R,5R,6R)-6-(4-nitrobenzyl)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane trifluoromethanesulfonate 
• 1269141-80-1 (1R,4R,5R,6R)-6-(4-(trifluoromethyl)benzyl)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane trifluoromethanesulfonate 
• 1269141-74-3 (1R,4R,5R,6R)-6-(3-methoxybenzyl)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane trifluoromethanesulfonate 

Relevant academic research and scientific papers

Synthesis process of isothiocineole

The invention discloses a synthesis process of isothiocineole, and relates to the technical field of synthesis of isothiocineole. Alpha-terpineol is taken as an initial raw material, and is sequentially subjected to halogenation reaction, nucleophilic substitution reaction, elimination reaction and Michael addition reaction to prepare a crude isothiocineole product, and the crude isothiocineole product is rectified to obtain a pure isothiocineole product. The synthesis process has the advantages of high yield, low cost, simple operation, suitability for industrial production and the like.

Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.

Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: Extensive studies to map out scope, limitations, and rationalization of diastereo- and enantioselectivities

The chiral sulfide, isothiocineole, has been synthesized in one step from elemental sulfur, γ-terpinene, and limonene in 61% yield. A mechanism involving radical intermediates for this reaction is proposed based on experimental evidence. The application of isothiocineole to the asymmetric epoxidation of aldehydes and the aziridination of imines is described. Excellent enantioselectivities and diastereoselectivities have been obtained over a wide range of aromatic, aliphatic, and α,β-unsaturated aldehydes using simple protocols. In aziridinations, excellent enantioselectivities and good diastereoselectivities were obtained for a wide range of imines. Mechanistic models have been put forward to rationalize the high selectivities observed, which should enable the sulfide to be used with confidence in synthesis. In epoxidations, the degree of reversibility in betaine formation dominates both the diastereoselectivity and the enantioselectivity. Appropriate tuning of reaction conditions based on understanding the reaction mechanism enables high selectivities to be obtained in most cases. In aziridinations, betaine formation is nonreversible with semistabilized ylides and diastereoselectivities are determined in the betaine forming step and are more variable as a result.

Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine

(Chemical Presented) Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aromatic and aliphatic aldehydes gave epoxides with perfect enantioselectivities and the highest diastereoselectivities reported to date. In addition reactions with imines gave aziridines again with the highest enantioselectivities and diastereoselectivities reported to date. The reactions are scaleable, and the sulfide can be reisolated in high yield. The epoxidation has been used as the key step in a convergent and stereoselective synthesis of each of the diastereoisomers of the cinchona alkaloids, quinine and quinidine. Copyright

REACTION OF SULFUR HALIDES WITH UNSATURATED COMPOUNDS. XX. REACTION OF SULFUR DICHLORIDE WITH 1-METHYL-4-ISOPROPENYL- AND 1,4-DIMETHYL-4-VINYL-1-CYCLOHEXENES. SYNTHESIS OF THIABICYCLOOCTANES AND THIABICYCLONONANES

The reaction of 1-methyl-4-isopropenyl- and 1,4-dimethyl-4-vinyl-1-cyclohexenes with sulfur dichloride gave the corresponding methyl-substituted dichlorothiabicyclononanes.Reductive dechlorination of the latter led to mixtures of isomeric thiabicyclanes, from which dimethyl- and trimethyl-substituted 2-thiabicyclo- and 6-thiabicyclooctanes and 2-thiabicyclo- and 2-thiabicyclononanes were isolated; the effect of the nature of the reducing agent and the conditions on the isomeric composition of the thiabicyclanes was demonstrated.Acetolysis of 4,8-dichloro-5,8-dimethyl-2-thiabicyclononane is accompanied by the formation of two isomeric thiabicyclononadienes in addition to the corresponding hydroxy and acetoxy derivatives.