2230-91-3

Upstream product

• 89-78-1 menthol 
• 104-15-4 toluene-4-sulfonic acid 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 2216-52-6 Neomenthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 

Downstream Products

• 148180-36-3 (+)-3-<(1'R,2'R,5'R)-2'-isopropyl-5'-methylcyclohexyl>indene 
• 148200-42-4 (1-neoisomenthylindenyl)lithium 
• 1044169-00-7 (-)-(1R,2R,5R,1'R,2'R,5'R)-dineoisomenthyl diselenide 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 196622-67-0 (1R,3R,4R)-p-menthane-3-thiol 
• 139756-61-9 (1R,2S,5R)-1-cyclopentadienyl-cis-5-methyl-trans-2-(2-propyl)cyclohexane 
• 891826-22-5 cyclopenta-1,3-dienyl-(1S,2S,5R)-4-methyl-1-(prop-2-yl)-cyclohexane 
• 619-52-3 (1R)-menth-3-ene 
• 854823-95-3 4-chloro-p-menthane 
• 91138-81-7 8-chloro-p-menthane 
• 1372878-68-6 2-{[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfonyl}-1H-imidazole 
• 1372878-72-2 1-methyl-2-{[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfonyl}-1H-imidazole 
• 1372878-76-6 2-{[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfonyl}-1H-benzimidazole 
• 1355709-97-5 2-[((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)sulfanyl]-1H-imidazole 

Relevant academic research and scientific papers

Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

1-p-Menthene-8-thiol (1) has been discovered as the key odorant in grapefruit juice several decades ago and contributes to the overall odor of the fruit with an extremely low odor threshold of 0.000034 ng/L in air. This value is among the lowest odor thresholds ever reported for a food odorant. To check whether modifications in the structure of 1 would lead to changes in odor threshold and odor quality, 34 mercapto-containing p-menthane and 1-p-menthene derivatives as well as several aromatic and open-chain mercapto monoterpenoids were synthesized. Eighteen of them are reported for the first time in the literature, and their odor thresholds and odor qualities as well as analytical data are supplied. A comparison of the sensory data with those of 1 showed that hydrogenation of the double bond led to a clear increase in the odor threshold. Furthermore, moving the mercapto group into the ring always resulted in higher odor thresholds compared to thiols with a mercapto group in the side chains. Although all tertiary thiols always exhibited low odor thresholds, none of the 31 compounds reached the extremely low threshold of 1. Also, none of the synthesized mercapto monoterpenoids showed a similar odor quality resembling grapefruit. Although the saturated and aromatic analogues exhibited similar scents as 1, the aromas of the majority of the other compounds were described as sulfury, rubber-like, burned, soapy, or even mushroom-like. NMR and MS data as well as retention indices of the 23 newly reported sulfur-containing compounds might aid in future research to identify terpene-derived mercaptans possibly present in trace levels in foods.

Chirality transfer through sulfur or selenium to chiral propellers

The mechanism of chirality transfer from a chiral alkyl substituent to a trityl moiety through sulfur or selenium atoms is analysed and discussed on the basis of ECD measurements, DFT structure and ECD spectra calculations. It is shown that the presence o

Synthesis of new monoterpene sulfonylimidazoles

Sulfonylimidazoles of monoterpenes of menthane, pinane, and carane nature were synthesized in 83-98% yields.

Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups

(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.

Synthesis and reactions of enantiomerically pure dialkyl diselenides from the p-menthane group

A convenient route for the synthesis of optically active dialkyl diselenides from the p-menthane system utilizing a reaction of alkyl tosylates and chlorides with sodium diselenide is reported. The diselenides obtained have been used for asymmetric methoxyselenenylation of styrene. Quantum chemical calculations of the chair conformers stability of the terpeneselenenyl bromides from the p-menthane group have also been carried out using density functional theory (DFT, at the B3LYP/6-311G(d) level). The influence of the diselenides structure on the stereoselectivity in the methoxyselenenylation reaction is also discussed.

Syntheses and reactions of new optically active terpene dialkyl diselenides

The reaction of sodium diselenide with optically active alkyl tosylates or chlorides is found to be a useful method for the synthesis of optically active dialkyl diselenides. Optically active monoterpene diselenides derived from menthane, carane, pinane,

An efficient and selective tosylation of alcohols with p-toluenesulfonic acid

Silica chloride has been found to be an efficient catalyst for facile tosylation of alcohols directly with p-toluenesulfonic acid in methylene chloride under reflux. The process is associated with selective tosylation of secondary alcohols over primary al

Cobalt(II) catalyzed tosylation of alcohols with p-toluenesulfonic acid

Cobalt(II) chloride hexahydrate (CoCl2·6H2O) has been found to catalyze the tosylation of both aliphatic and aromatic alcohols with p-toluenesulfonic acid (p-TsOH) in high yields in 1,2-dichloroethane under reflux (ca. 80°C). In the

ZrCl4 as an efficient catalyst for selective tosylation of alcohols with p-toluenesulfonic acid

Tosylation of alcohols has directly been carried out with p-toluenesulfonic acid in methylene chloride under reflux using ZrCl4 as a catalyst. Primary alcohols were found to be tosylated chemoselectively over secondary alcohols.

Mechanisms of stereocontrol for doubly silylene-bridged Cs- and Cl-symmetric zirconocene catalysts for propylene polymerization. Synthesis and molecular structure of Li2[(1,2-Me2Si)2{C5H

Doubly [SiMe2]-bridged metallocenes (1,2-SiMe2)2{η5-C5H 2-4-R}{η5-C5H-3,5-(CHMe2) 2}ZrCl2 (R = H (1a), CHMe2 (1b), SiMesub