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.
Preparation method of muskmelon aldehyde, muskmelon aldehyde and application thereof
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, (2020/07/12)
The invention relates to a preparation method of muskmelon aldehyde, muskmelon aldehyde and an application thereof, the preparation method comprises the following steps: carrying out a Darzen condensation reaction on 6-methyl-5-heptene-2-ketone, chloroacetate and an acid-binding agent under the condition of adding a solvent and a phase transfer catalyst to obtain epoxy caprylate; and saponifying the obtained epoxy caprylate in an aqueous solution of alkali to generate corresponding salt, acidifying with acid to obtain 3, 7-dimethyl-6-ene-2, 3-epoxy caprylic acid, carrying out a reduced pressure decarboxylation reaction on 3, 7-dimethyl-6-ene-2, 3-epoxy caprylic acid, and adding a mixture composed of an antioxidant and a polymerization inhibitor to obtain the muskmelon aldehyde product. Theconditions of the preparation method are easier to control, the production is safer, the yield is higher, and the product purity is high.