2344-71-0Relevant academic research and scientific papers
The biogenic amine transporter activity of vinylogous amphetamine analogs
Decker, Ann M.,Partilla, John S.,Baumann, Michael H.,Rothman, Richard B.,Blough, Bruce E.
supporting information, p. 1657 - 1663 (2016/08/24)
A series of vinylogous amphetamine analogs was synthesized and examined for their activity at biogenic amine transporters and serotonin-2 receptor (5-HT2) subtypes. (1S,3E)-1-Methyl-4-phenyl-but-3-enylamine (S-6) is a potent dual dopamine/serotonin (DA/5-HT) releaser with no activity at 5-HT2 receptors. This unique profile of actions suggests that analog S-6 is a viable lead compound for identifying new structural classes of DA/5-HT releasers with therapeutic benefit and reduced abuse liability.
Chemical modification of lipase for rational enhancement of enantioselectivity
Ema, Tadashi,Inoue, Hiroki
supporting information, p. 1374 - 1376 (2015/11/24)
Chemical modifications of the I287C mutant of a Burkholderia cepacia lipase afforded various I287C-X conjugates, among which I287C-PAA bearing an N-phenylacetamide (PAA) moiety showed excellent enantioselectivity and catalytic activity for secondary alcohols. Site-directed chemical modifications are powerful tools to control enantioselective biocatalysis.
Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes
Joannou, Matthew V.,Moyer, Brandon S.,Meek, Simon J.
supporting information, p. 6176 - 6179 (2015/06/02)
The first catalytic enantio- and diastereoselective synthesis of 1,2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., and 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the α-boryl component.
Iron-catalyzed arene alkylation reactions with unactivated secondary alcohols
Jefferies, Latisha R.,Cook, Silas P.
, p. 2026 - 2029 (2014/05/06)
A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.
Levonantradol: Asymmetric synthesis and structural analysis
Sheshenev, Andrey E.,Boltukhina, Ekaterina V.,Hii, King Kuok
, p. 3685 - 3687 (2013/05/09)
The first asymmetric synthesis of a synthetic cannabinoid levonantradol was accomplished, and the 3-D solution structure of its core architecture was confirmed by NMR and computational methods. The Royal Society of Chemistry 2013.
Copper(I)-catalyzed boryl substitution of unactivated alkyl halides
Ito, Hajime,Kubota, Koji
, p. 890 - 893 (2012/05/05)
Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.
Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes
Prokofjevs, Aleksandrs,Boussonniere, Anne,Li, Linfeng,Bonin, Helene,Lacote, Emmanuel,Curran, Dennis P.,Vedejs, Edwin
supporting information; experimental part, p. 12281 - 12288 (2012/09/22)
Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N-heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf 2 (Tf = trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3-hexene, surprisingly facile migration of the boron atom from C(3) of the hexyl group to C(2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of alcohols containing 2-hexanol as the major product. A similar preference for the C(2) alcohol was observed after oxidative workup of the 3-octene and 1-cyclohexyl-1-butene hydroborations. NHC-borenium cations (or functional equivalents) are postulated as the species that accomplish the hydroborations, and the C(2) selective migrations are attributed to the four-center interconversion of borenium cations with cationic NHC-borane-olefin π-complexes.
A facile preparation of tetralins from arene-1,4-diones using titanium(IV) chloride and triethylsilane
Li, Gang,Xiao, Qiong,Li, Chun,Wang, Xiaojian,Yin, Dali
scheme or table, p. 6827 - 6830 (2011/12/22)
A facile method for the synthesis of tetralins has been described which uses various substituted phenylpentane-1,4-diones as starting material with a combination of TiCl4/Et3SiH. The synthesis involves three reactions under mild conditions. A mechanism has been proposed for the reductive cyclization through ionic hydrogenation, and titanium(IV) chloride catalyzed cyclization.
Copper-catalyzed remote sp3 C-H chlorination of alkyl hydroperoxides
Kundu, Rituparna,Ball, Zachary T.
supporting information; experimental part, p. 2460 - 2463 (2010/07/05)
A copper-catalyzed methodology to functionalize remote sp3 C-H bonds in alkyl hydroperoxides is presented. The atom-transfer chlorination utilizes simple ammonium chloride salts as the chlorine source, and the internal redox process requires no external redox reagents.
Samarium diiodide mediated ketyl-aryl coupling reactions - Influence of substituents and trapping experiments
Wefelscheid, Ulrike K.,Berndt, Mathias,Reissig, Hans-Ulrich
experimental part, p. 3635 - 3646 (2009/06/06)
This comprehensive study describes the influence of substituents at the aryl moiety on SmI2-mediated intramolecular ketyl-aryl coupling reactions. Differently substituted γ-aryl ketones were employed as precursors, which were directly prepared
