22627-70-9Relevant articles and documents
Challenging the Molecular Parameters of Vetiver: Can 4,5-Dimethyl-3-(3′-methylbut-1′-en-2′-yl)-4-phenylcyclopent-2-en-1-one Mimic Zizaenones in Structure and Odor?
Pfaff, Patrick,Mouhib, Halima,Kraft, Philip
, p. 2643 - 2652 (2019)
In order to investigate the molecular parameters of vetiver odorants and scrutinize the significance of ziza-6(13)-en-3-ones as structural templates in the design of new vetiver odorants, 4,5-dimethyl-3-(3′-methylbut-1′-en-2′-yl)-4-phenylcyclopent-2-en-1-one (10) was synthesized in 6 steps from cyclopentane-1,3-dione (20) following a Stork–Danheiser strategy after synthetic approaches by Ni-catalyzed [3+2] annulation and enyne metathesis had failed. Addition of EtOH, α-methylation of the resulting vinylogous ester 18, Pd-catalyzed α-arylation, and CeCl3·2LiCl mediated alkylation with (3-methylbut-1-en-2-yl)lithium, generated by Shapiro reaction from the corresponding hydrazone 23, furnished after a concluding α-methylation the target compound that possessed only a weak woody odor devoid of typical vetiver characteristics. While the design approach utilizing London dispersion forces could not reveal the secret of vetiver, it showed that the molecular parameters are far more complex than initially expected.
An efficient synthesis of 3-aminocyclopent-2-en-1-one
Kikani,McKee,Zanger
, p. 176 - 176 (1991)
A two step, efficient synthesis of the key intermediate 3-aminocyclopent-2-en-1-one starting from 1,3-cyclopentanedione is described. This involves the reaction of ammonia gas with 3-ethoxycyclopent-2-en-1-one.
CDK4/6 INHIBITOR AND PHARMACEUTICALLY ACCEPTABLE SALT AND POLYMORPH THEREOF AND USE THEREOF
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Paragraph 0361; 0375; 0376, (2021/07/17)
Provided are a CDK4/6 inhibitor, a pharmaceutically acceptable salt thereof and a polymorph thereof, and the use thereof. In particular, provided are a polymorph of 2-cyclopropyl-N-(5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-yl)-3-isopropyl-3,8-dihydroimidazo[4′,5′,4,5]cyclopentadieno[1,2-d]pyrimidin-5-amine and a pharmaceutically acceptable salt thereof, and the use thereof. In addition, further disclosed are a pharmaceutical composition of the compound and the use thereof.
Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications
Poplata, Saner,Bauer, Andreas,Storch, Golo,Bach, Thorsten
supporting information, p. 8135 - 8148 (2019/05/29)
The intramolecular [2+2] photocycloaddition of 3-alkenyl-2-cycloalkenones was performed in an enantioselective fashion (nine representative examples, 54–86 % yield, 76–96 % ee) upon irradiation at λ=366 nm in the presence of an AlBr3-activated oxazaborolidine as the Lewis acid. An extensive screening of proline-derived oxazaborolidines showed that the enantioface differentiation depends strongly on the nature of the aryl group at the 3-position of the heterocycle. DFT calculations of the Lewis acid–substrate complex indicate that attractive dispersion forces may be responsible for a change of the binding mode. The catalytic [2+2] photocycloaddition was shown to proceed on the triplet hypersurface with a quantum yield of 0.05. The positive effect of Lewis acids on the outcome of a given intramolecular [2+2] photocycloaddition was illustrated by optimizing the key step in a concise total synthesis of the sesquiterpene (±)-italicene.