The Rohlin property for automorphisms of the Jiang-Su algebra

For projectionless C^∗-algebras absorbing the Jiang-Su algebra tensorially, we study a kind of the Rohlin property for automorphisms. We show that the crossed products obtained by automorphisms with this Rohlin property also absorb the Jiang-Su algebra tensorially under a mild technical condition on the C^∗-algebras. In particular, for the Jiang-Su algebra we show the uniqueness up to outer conjugacy of the automorphism with this Rohlin property.     

Microwave assisted synthesis of the fragrant compound Calone 1951

Calone 1951^®, 7-methyl-benzo[b][1,4]dioxepin-3-one, possesses a strong marine, ozone note with floral nuances and is synthesised via a three-step procedure using microwave irradiation. High yields were obtained, and reaction times reduced to a few minutes, allowing for an efficient and inexpensive synthesis of Calone 1951^®.     

Synthesis and Qualitative Olfactory Evaluation of Benzodioxepine Analogues

Marine fragrances, particularly Calone 1951^® (=7‐methyl‐2H‐1,5‐benzodioxepin‐3(4H)‐one; 1 ) has carved a minor but distinct niche in the broad field of fragrance chemistry. By focusing on the polar structure fragment of the benzodioxepinone parent compound, we set out to determine the molecular influence on the dominant marine note attributed to the Calone 1951^® structure. A selection of one‐step modifications of the ketone 1 resulted in a range of odor‐active conformers with diverse olfactory attributes. The synthesis of a range of benzodioxepine analogues, i.e., of 3 – 11 , is presented alongside olfactory evaluation (Tables 2 and 3). Removal of the carbonyl group of 1 and increasing the size of the aliphatic ring portion (see 6 and 7 ) introduced sweetness and a predominant loss of the marine character.     

Synthesis of Benzodioxepinone Analogues via a Novel Synthetic Route with Qualitative Olfactory Evaluation

Marine odorants represent a minor yet diverse class of substances within the fragrance industry, of which 7‐methyl‐2H‐1,5‐benzodioxepin‐3(4H)‐one ( 1 ) is commercially known as Calone 1951^®, a synthetic first in the area of marine‐fragrance chemistry. To determine the extent to which the characteristic marine odor of Calone 1951^® corresponds to the substitution at the benzo portion of the molecule, a variety of aromatic substituents were incorporated into the benzodioxepinone structure (Scheme 1, Table 3). In light of the difficulty experienced in applying patented literature to deriving the analogues 12 – 18 , particularly those with electron‐withdrawing substituents, an alternative synthetic scheme was implemented for the construction of all analogues in favorable yields (Scheme 4, Table 3). Formation of the hydroxy‐protected dihalo alkylating agent 24 via epoxide cleavage of epichlorohydrin (Scheme 3) allowed etherification favoring dihalo displacement and subsequent intramolecular ring closure (→ 26a – g ). THP Deprotection followed by oxidation of the alcohols 27a – g to the ketones 12 – 18 provided a general pathway to the benzodioxepinone products. The influence of the substituent nature on odor activity revealed a diverse scope of olfactory character (Table 4).     

Structure–Activity Relationship in the Domain of Odorants Having Marine Notes

We synthesized or re‐synthesized a large series of 2H‐1,5‐benzodioxepin‐3(4H)‐ones 9 (Scheme 1), 4,5‐dihydro‐1‐benzoxepin‐3(2H)‐ones 10 (Schemes 3 and 4) and 5,6,8,9‐tetrahydro‐7H‐benzocyclohepten‐7‐ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well‐known benzodioxepinone named Calone 1951^® ( 9b ). We meticulously described the odor profile of each synthesized compound and discussed relevant structure–odor relationships (Tables 1–3). In particular, we revealed a correlation between the conformation of the seven‐membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.