53439-16-0Relevant articles and documents
Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays
Mosaferi, Shabnam,Jelley, Rebecca E.,Fedrizzi, Bruno,Barker, David
supporting information, (2020/12/02)
C13 Norisoprenoids are important aroma compounds in wine, giving positive attributes to the overall wine aroma even when found at very low levels. β-Ionone is considered one of the most important aroma compounds giving violet, woody and raspberry aromas to wine, fruits and vegetables in which it is found. Due to its potent aroma at low levels, precise analytical methods are desired for its quantification. Stable isotope dilution assay (SIDA) is one of the most important of these methods but requires the use of isotopically labelled standards. Herein, we describe the scalable synthesis of d6-β-ionone and d6-β-cyclocitral, another aroma compound with smokey and fruity notes, starting from the relatively inexpensive deuterated starting material d6-acetone.
Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives
Maeda, Hajime,Wada, Hidenori,Mukae, Hirofumi,Mizuno, Kazuhiko
, p. 29 - 41 (2016/11/16)
Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.
Development of an intramolecular aryne ene reaction and application to the formal synthesis of (±)-crinine
Candito, David A.,Dobrovolsky, Dennis,Lautens, Mark
supporting information, p. 15572 - 15580 (2012/11/07)
A general and high yielding annulation strategy for the synthesis of various carbo- and heterocycles, based on an intramolecular aryne ene reaction is described. It was found that the geometry of the olefin is crucial to the success of the reaction, with exclusive migration of the trans-allylic-H taking place. Furthermore, the electronic nature of the aryne was found to be important to the success of the reaction. Deuterium labeling studies and DFT calculations provided insight into the reaction mechanism. The data suggests a concerted asynchronous transition state, resembling a nucleophilic attack on the aryne. This strategy was successfully applied to the formal synthesis of the ethanophenanthridine alkaloid (±)-crinine.