106-72-9Relevant articles and documents
Stereochemistry of female-specific normonoterpenes, sex pheromone candidates from the acarid mite, Tyreophagus sp. (Astigmata: Acaridae)
Shimizu, Nobuhiro,Miwa, Kuniaki,Noge, Koji,Yakumaru, Ryota,Mori, Naoki,Kuwahara, Yasumasa
, p. 2332 - 2334 (2009)
Two normonoterpenes were detected from an unidentified Tyreophagus sp. as new female-specific components. Both planar structures were identified to be 2,6-dimethyl-5-heptenal (1) and 2,6-dimethyl-5-hepten- 1-ol (2) by GC/MS co-chromatography with synthetic 1 and 2. The stereochemistry of 2 was determined to be R by a GC analysis with a chiral column, while that of 1 was presumed to be similar to 2 based on the biosynthetic aspects.
Semiochemicals of the scarabaeinae. VII: Identification and synthesis of ead-active constituents of abdominal sex attracting secretion of the male dung beetle, Kheper subaeneus
Burger,Petersen,Weber,Munro
, p. 2527 - 2539 (2002)
Using gas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, butanoic acid, skatole, and (E)-2,6-dimethyl-6-octen-2-ol were identified as constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper subaeneus, which reproducibly elicited EAD responses in male and female antennae. This is the first report of the occurrence of (E)-2,6-dimethyl-6-octen-2-ol as a natural product, for which the name (E)-subaeneol is proposed. In some experiments, a few other constituents of the secretion also gave reproducible responses in specific male and female antennae but did not elicit responses when the analyses were repeated with other antennae. The major volatile constituent of the secretion, identified as (S)-(+)-2,6-dimethyl-5-heptenoic acid, is one of these EAD-active compounds. Both this compound and (E)-2,6-dimethyl-6-octen-2-ol were synthesized from authentic starting materials for comparison with the natural products.
A study towards the synthesis of (-)-atrop-abyssomicin C core
Sai?i?, Radomir N.,Trm?i?, Milena
, p. 1305 - 1315 (2022/02/19)
An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation.
Process for industrially producing muskmelon aldehyde
-
Paragraph 0027-0034, (2020/08/09)
The invention discloses a process for industrially producing muskmelon aldehyde. 1-methyl-3-propylimidazolium hexafluorophosphate ionic liquid is used as a catalyst and a solvent, methyl 3,7-dimethyl-6-ene-2,3-epoxy caprylate is used for obtaining the melonal in one step, and meanwhile, through sectional heating reaction control, the reaction selectivity and the catalytic reaction rate can be improved, the reaction is effectively promoted, and the yield of the melonal is increased and can reach 95% or above. According to the process provided by the invention, the use of hydrogen bromide or hydroiodic acid with strong corrosivity is avoided, the requirements on equipment materials are reduced, the product is easy to separate, the operation is simple and convenient, and the industrial production is facilitated.