110718-87-1Relevant articles and documents
Synthesis and antialgal activity of dihydrophenanthrenes and phenanthrenes II: Mimics of naturally occurring compounds in Juncus effusus
Dellagreca,Fiorentino,Monaco,Pinto,Previtera,Zarrelli
, p. 257 - 271 (2001)
9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling by zerovalent Ni of 1-(2-iodo-5-methoxy)-phenylethanol or 2-iodo-5-methoxyacetophenone with iodoxylenes. The synthetic compounds had a hydroxyl or a methoxyl group at C-2 and two methyls in the C ring. Assays on the green alga Selenastrum capricornutum showed that all the compounds, except 2-methoxy-5,7-dimethylphenanthrene, caused strong inhibition of algal growth at 10-4 M. 2-Hydroxy-7,8-dimethyl-9,10-dihydrophenanthrene and 2-methoxy-5,6-dimethylphenanthrene fully inhibited growth at 10-5 M.
Palladium-catalyzed: Ortho -halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids
Ram, Shankar,Sharma, Ajay Kumar,Chauhan, Arvind Singh,Das, Pralay
supporting information, p. 10674 - 10677 (2020/10/02)
The 2-vinylbenzoic acids have wide applications in the field of polymer chemistry and are key precursors for the synthesis of important bioactive molecules. Herein, an ortho-halogen-induced deoxygenative approach for the generation of 2-vinylbenzoic acids from alkyl aryl ketones by palladium catalysis is discovered and explored. This approach requires no base or stoichiometric additives and can be carried out through a simple one-step process. Furthermore, the present reaction is scalable up to one-gram scale. The commercially available palladium on carbon (5 wt%) was used as a heterogeneous catalyst and showed excellent recyclability (5 times) without significant loss in catalytic activity. Pleasingly, under our optimized conditions, the alpha alkyl substituted 2-iodoacetophenones exhibit good diastereoselectivity and predominantly (E)-2-vinylbenzoic acids were obtained with good to excellent yields.
Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)?H Activation and Naphthol Dearomatization
Tan, Bojun,Bai, Lu,Ding, Pin,Liu, Jingjing,Wang, Yaoyu,Luan, Xinjun
, p. 1474 - 1478 (2019/01/09)
A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp3)?H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation-facilitat
A conjunctive carboiodination: Indenes by a double carbopalladation- reductive elimination domino process
Jia, Xiaodong,Petrone, David A.,Lautens, Mark
supporting information, p. 9870 - 9872 (2012/10/30)
Something gained, nothing lost: A Pd0-catalyzed domino intermolecular/intramolecular process terminated by carbohalogenation is reported. In this reaction, two new C-C bonds, one new C-I bond and one five-membered ring are formed in a single step, and all of the atoms in the starting materials are incorporated into the product (see scheme). Copyright
Solvent directed electrophilic iodination and phenylselenenylation of activated alkyl aryl ketones
Panunzi, Barbara,Rotiroti, Lucia,Tingoli, Marco
, p. 8753 - 8756 (2007/10/03)
A mixture of molecular iodine and phenyliodine(III) bis(trifluoroacetate) (BTI) in CH3CN (or CH3OH) iodinates the aromatic ring of some activated alkyl aryl ketones. A different outcome results if PhSeSePh is used instead of I2
Dihydrophenanthrene and phenanthrene mimics of natural compounds - Synthesis and antialgal activity
Dellagreca,Fiorentino,Monaco,Pollio,Previtera,Zarrelli
, p. 587 - 600 (2007/10/03)
9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling of 1-(2-iodo-5-methoxy)-phenylethanol with variously substituted iodobenzenes. The synthetic compounds, bearing a hydroxyl or a methoxyl group at C-2 and a methyl in the C ring, were tested against the green alga Selenastrum capricornutum. All compounds, except 2-methoxy-7- methylphenanthrene, caused inhibition of algal growth by more than 70% at 10-4 M, and many of them retained this strong activity at 10-5 M.
New chiral hypervalent iodine compounds in asymmetric synthesis
Hirt, Urs H.,Spingler, Bernhard,Wirth, Thomas
, p. 7674 - 7679 (2007/10/03)
The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrène and in the a-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.
