89449-82-1Relevant articles and documents
Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes
Khotyantseva, Elizaveta A.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Ioffe, Sema L.
supporting information, p. 3128 - 3131 (2018/07/13)
A new method for the synthesis of conjugated silyl nitronates from nitroalkenes is described. The procedure has wide substrate scope and is compatible with in situ generation of the substrates from 2-nitroalcohols or 2-chloro-nitroalkanes. A cascade transformation to give 3,4,5,6-tetrahydropyridine N-oxide derivatives was disclosed.
Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene
Akula, Pavan Sudheer,Hong, Bor-Cherng,Lee, Gene-Hsiang
supporting information, p. 7835 - 7839 (2019/01/04)
The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.
Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction
Nonoyama, Akihito,Hashimoto, Kazuki,Saito, Akira,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 1815 - 1819 (2016/04/05)
A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensi
Chiral 1,1′-binaphthylazepine derived amino alcohol catalyzed asymmetric Henry reaction
Guo, Zong-Liang,Zhong, Shi,Li, Yong-Bo,Lu, Gui
experimental part, p. 238 - 245 (2011/05/04)
The catalytic asymmetric Henry reaction of nitromethane to various aldehydes has been developed using a chiral binaphthylazepine derived amino alcohol and Cu(OAc)2·H2O as the catalyst. High yields and good enantioselectivities (up to
A highly diastereo-and enantioselective copper(I)-catalyzed henry reaction using a bis(sulfonamide)-diamine ligand
Jin, Wei,Li, Xincheng,Wan, Boshun
experimental part, p. 484 - 491 (2011/04/15)
A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantios
CHIRAL TETRAAMINOPHOSPHONIUM SALTS, CATALYST FOR ASYMMETRIC SYNTHESIS AND METHOD FOR PRODUCING CHIRAL beta-NITROALCOHOL
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Page/Page column 9-10, (2009/05/28)
A chiral tetraaminophosphonium salt represented by formula (1) and a method for producing chiral β-nitroalcohol comprising reacting an aldehyde or a ketone and a nitroalkane in the presence of the chiral tetraaminophosphonium salt represented by formula (
Selective nitroaldol condensations over heterogeneous catalysts in the presence of supercritical carbon dioxide
Ballini, Roberto,Noe, Marco,Perosa, Alvise,Selva, Maurizio
supporting information; experimental part, p. 8520 - 8528 (2009/04/05)
(Chemical Equation Presented) At 40-60°C, in the presence of heterogeneous catalysts based on Al2O3, supercritical carbon dioxide not only acts as a good solvent for the reaction of aromatic and aliphatic aldehydes with 1-nitroalkanes but, most importantly, it also allows the selectivity to be tuned between the competitive formation of β-nitroalcohols and nitroalkenes (from the Henry reaction and the nitroaldol condensation, respectively). In particular, when the pressure (and the density) of the supercritical phase is enhanced from 80 to 140 bar, the nitroalkene's selectivity increases, on average, from ~60 to >90%. Experiments show that, in the same pressure range, a steep increase of the concentration profiles of reactant aldehydes takes place. By contrast, under solvent-free conditions, the reaction usually proceeds with a higher conversion, but nitroalkanols are the major products.
Henry reaction and 1,4-addition of nitroalkanes to α,β- unsaturated carbonyl compounds under the influence of MS 4 A in DMSO
Oriyama, Takeshi,Aoyagi, Masaru,Iwanami, Katsuyuki
, p. 612 - 613 (2008/02/07)
In the presence of MS 4 A in DMSO (dimethyl sulfoxide), Henry reaction with various carbonyl compounds and nitroalkanes proceeded smoothly to give the corresponding β-nitroalcohol without a base catalyst. Moreover, 1,4-additon of nitroalkane to α,β-unsaturated ketones was also performed in DMSO. Copyright
On the [2,3] sigmatropic rearrangement of allylic nitro compounds
Alameda-Angulo, Celia,Quiclet-Sire, Beatrice,Schmidt, Elmar,Zard, Samir Z.
, p. 3489 - 3492 (2007/10/03)
(Chemical Equation Presented) Allylic nitro compounds undergo relatively clean [2,3] sigmatropic rearrangement upon heating in refluxing 1,2-dichlorobenzene in the presence of DABCO to give the corresponding allylic alcohols via the intermediate allylic n
Pyrrole and pyrazole DAAO inhibitors
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Page/Page column 65-66, (2008/06/13)
Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R1 and R2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR5; or R1 and R2, taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR6R7)n; R3 is hydrogen, alkyl or M+; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR4; R4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR5; R5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R6 and R7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R1, R2 and R4 is other than hydrogen; and at least one of X and Y is (CR6R7)n. D-serine or cycloserine may be coadministered along with the compound of formula I.