51171-71-2Relevant articles and documents
A vicarious, one-pot synthesis of benzo- and naphthofurans: Applications to the syntheses of stereumene B and paeoveitols
Rashid, Showkat,Bhat, Bilal A.,Mehta, Goverdhan
supporting information, p. 1122 - 1125 (2019/03/26)
An interesting albeit unexpected deviation during attempted Tanabe γ-lactone annulation on 4-hydroxycyclohexanones has led to a general, one-pot synthesis of benzofurans and naphtho[2,3–b]furans from readily assembled precursors. The utility of this adaptable methodology has been demonstrated through concise syntheses of natural products, stereumene B, paeoveitol D and (±)-paeoveitol.
Visible Light Mediated Generation of trans-Arylcyclohexenes and Their Utilization in the Synthesis of Cyclic Bridged Ethers
Day, Jon I.,Singh, Kamaljeet,Trinh, Winston,Weaver, Jimmie D.
supporting information, p. 9934 - 9941 (2018/07/25)
While accessible via UV-irradiation of cis-cyclohexene, trans-cyclohexene has thus far been an investigation driven by curiosity, and due primarily to its short lifespan, has until recently not been employed for productive synthesis. Herein, we present st
Straightforward synthesis of nonconjugated cyclohex-3-enone and conjugated 4-methylenecyclohex-2-enone derivatives
Kuttner, Julian R.,Warratz, Svenja,Hilt, Gerhard
, p. 1293 - 1303 (2012/06/30)
The synthesis of nonconjugated cyclohex-3-enones via the regiodivergent cobalt-catalysed Diels-Alder reactions of 2-(trimethylsilyloxy)buta-1,3-diene with alkynes and hydrolysis of the dihydroaromatic intermediates is described. The application of bidentate phosphine ligands versus pyridine-imine ligands led to the regioselective formation of one out of the two possible regioisomeric products when terminal or unsymmetrically substituted alkynes were applied. The cyclohex-3-enone products were isolated mostly in good yields without isomerisation of the carbon-carbon double bond into conjugation based on the mild reaction conditions. The use of acetoxymethyl-substituted alkynes led to the conjugated 4-methylenecyclohex-2-enones after deprotection of the silyl enol ether. Georg Thieme Verlag Stuttgart · New York.
Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors
Ekkati, Anil R.,Mandiyan, Valsan,Ravindranathan, Krishna P.,Bae, Jae H.,Schlessinger, Joseph,Jorgensen, William L.
scheme or table, p. 2228 - 2231 (2011/05/05)
Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC50 of 6 μM for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties.
Cobalt(I)-catalyzed neutral Diels-Alder reactions of oxygen-functionalized acyclic 1,3-dienes with alkynes
Hilt, Gerhard,Smolko, Konstantin I.,Lotsch, Bettina V.
, p. 1081 - 1084 (2007/10/03)
The cobalt-catalyzed Diels-Alder reaction of alkoxy-substituted 1,3-butadienes with terminal and internal alkynes is described. While the reaction of 1-alkoxy derivatives gave the aromatic hydrocarbons upon elimination of alcohol from the alkoxy-substituted dihydroaromatic intermediates, the reactions with 2-alkoxy derivatives generated stable dihydroaromatic enol ethers in good to excellent chemical yields and good to high regioselectivities for unsymmetrical starting materials. The enol ethers can be easily hydrolysed to the corresponding β,γ-unsaturated ketones in a one pot reaction sequence or used in cyclopropanation or other subsequent chemical transformations.
Extended chains of six-membered rings. I. Model studies and key intermediates
Cory,Walker,Zabel
, p. 799 - 807 (2007/10/02)
McMurry coupling of 4-phenylcyclohex-3-en-1-one and double addition of 1,4-dilithiobenzene and 4,4'-dilithiobiphenyl to cyclohexanones gives linear chains of three or four six-membered carbocyclic rings, including a potential intermediate in a proposed sy
Involvement of Exciplexes in the Photolysis of Aliphatic Ketones in Deuteriochloroform: CIDNP Evidence
Zhang, Mao-Xi,Liu, Zhong-Li,Wu, Lung-Min,Liu, You-Cheng
, p. 451 - 454 (2007/10/02)
Photolysis of 4-acetyl-4-ethoxyformylcyclohexanone and 4-acetyl-4-phenylcyclohexanone in deuteriochloroform showed an unusual polarization which suggests that a singlet exciplex of the ketone with deuteriochloroform may be involved in the Norrish type I reaction.KEY WORDS - Photolysis Ketones CIDNP Exciplex
1,5-DICARBONYL COMPOUNDS A GENERAL PREPARATION METHOD
Duhamel, P.,Hennequin, L.,Poirier, J. M.,Tavel, G.,Vottero, C.
, p. 4777 - 4786 (2007/10/02)
In this report, a general method for the preparation of 1,5-dicarbonyl compounds and six membered ring annelation is described.This method involves the reaction of hemiacetal vinylogs 1 with enol ethers 2 or 3 in the presence of a Lewis acid.This reaction was successfully applied to the enol ethers of α and α,α'-hindered ketones such as 2,2,6-trimethyl cyclohexanone. α-Cyperone and 6-epi-α-cyperone were obtained using this process.
The monoblocking of symmetrical diketones on insoluble polymer supports
Xu, Zhang-Huang,McArthur, Colin R.,Leznoff, Clifford C.
, p. 1405 - 1409 (2007/10/02)
A 1 percent crosslinked divinylbenzene-styrene copolymer, incorporating vicinal diol groups or their isopropylidene precursors, was used to form the monoacetals of the symmetrical diketones, p-diacetylbenzene, 1,2-cyclohexanedione, 1,3-cyclohexanedione, 1,4-cyclohexanedione, and 2,5-hexanedione.The free ketone groups reacted with phenylmagnesium bromide to give, in high yield, after acid hydrolysis from the polymer, the expected products such as 3-phenyl-2-cyclohexen-1-one from 1,3-cyclohexanedione.The 13C nmr spectra of some polymer-bound substrates and simple analogs are described.
4'-Fluoro-4-{[4-(phenyl)cyclohexyl]amino}butyrophenones and the salts thereof
-
, (2008/06/13)
This invention relates to novel 4-phenylcyclohexylamines embraced by the formula SPC1 Wherein ? is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof; R is selected from the group consisting of alkyl of from one through four carbon atoms, fluorine, chlorine, bromine, trifluoromethyl, nitro and alkoxy of from one through four carbon atoms; R' and R1 are selected from the group consisting of hydrogen and alkyl of from one through four carbon atoms; R2 is selected from the group consisting of hydrogen, alkyl of from one through four carbon atoms, alkanoyl of from one through three carbon atoms, alkylsulfonyl of from one through three carbon atoms, arylsulfonyl of from six through ten carbon atoms, alkylcarbamoyl wherein alkyl is from one through four carbon atoms, alkoxycarbonyl wherein alkyl is from one through four carbon atoms, ring monosubstituted aroylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms and bis (ring monosubstituted) arylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms; R1 and R2 when taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and monosubstituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and an acid addition salt thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (1) and novel derivatives thereof. The systemic administration to humans and animals of the novel compounds (1) depresses their central nervous systems.
