102790-02-3Relevant articles and documents
Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
Delcaillau, Tristan,Bismuto, Alessandro,Lian, Zhong,Morandi, Bill
supporting information, p. 2110 - 2114 (2019/12/24)
A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.
Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol
Schoenauer, Sebastian,Schieberle, Peter
, p. 3849 - 3861 (2016/06/01)
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.
Flavouring and odorant thiols from renewable natural resources by InIII-catalysed hydrothioacetylation and lipase-catalysed solvolysis
Dia, Reine-Marie,Belaqziz, Rim,Romane, Abderrahmane,Antoniotti, Sylvain,Du?ach, Elisabet
scheme or table, p. 2164 - 2167 (2010/06/13)
A chemoenzymatic access to thiol compounds, including ethyl 3-thiobutanoate, 3-thio-p-menthene and 8-thio-p-menthan-2-one, three compounds of interest in flavour and fragrance chemistry presenting various fruity notes, is proposed. It involves an indium(III)-catalysed hydrothioacetylation of renewable precursors followed by an enzymatic solvolysis of the obtained thioesters by lipases in aqueous or organic solvents.
