2687-97-0Relevant academic research and scientific papers
Stereocontrolled synthesis of the enantiomers of 1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)-propyl]-pyrrolidin-2-one
Kulig, Katarzyna,Holzgrabe, Ulrike,Malawska, Barbara
, p. 2533 - 2536 (2001)
The asymmetric synthesis of 1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)-propyl]-pyrrolidin-2-one 1 is described. Enantiomers of compound 1 were obtained using the Sharpless asymmetric dihydroxylation (AD) or hydrolytic kinetic resolution (HKR) methods. The enantiomers of compound 1, which were obtained by HKR had higher enantiomeric excesses than those which were synthesized by AD and epoxidation. The enantiomeric purity of the synthesized compounds was determinated by capillary electrophoresis.
Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling
Klake, Raphael K.,Edwards, Mytia D.,Sieber, Joshua D.
, p. 6444 - 6449 (2021)
Herein, we report the development of a catalytic enantioselective addition of N-substituted allyl equivalents to ketone electrophiles through use of Cu-catalyzed reductive coupling to access important chiral 1,2-aminoalcohol synthons in high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed including the identification of a reversible ketone allylation step that has not been previously reported in Cu-catalyzed reductive coupling.
Isoxazoline, isoxazole, and oxadiazole derivatives as M1 muscarinic acetylcholine receptor agonists
Muthusamy, Selvaraj,Lee, Soo Min,Huang, Minghua,Cho, Nam-Chul,Nam, Ghilsoo,Pae, Ae Nim,Rhim, Hyewhon,Keum, Gyochang,Choi, Kyung Il
, p. 1020 - 1028 (2016)
Insertion of a methylene linker between the 2-pyrrolidinone substituent and the isoxazoline core of the lead compound 1 previously reported resulted in the loss of its agonistic activity. One exception was the compound 6f having oxadiazole core and 2-azabicyclo[2.2.1]heptane substituent. Of the two isomers of 6f, exo-isomer (EC50 0.013 μM) was five-to six-fold more effective than endo-isomer (EC50 0.30 μM), and ca. two-fold active than the mother compound 1 (EC50 0.031 μM) in stimulating the M1 mAChR. Both isomers were moderately selective agonists for M1 mAChR over the rest four subtypes, and it could be explained by docking study on active conformation allosteric binding sites of M1-M5 mAChRs and calculating their binding energies.
Novel Pyrrolinium-based Ionic Liquids for Lithium Ion Batteries: Effect of the Cation on Physicochemical and Electrochemical Properties
Kim, Hyung-Tae,Kwon, Oh Min,Mun, Junyoung,Oh, Seung M.,Yim, Taeeun,Kim, Young Gyu
, p. 267 - 276 (2017)
Lithium ion batteries (LIBs) are one of the most promising energy conversion/storage systems, but the low thermal stability of the current electrolytes in LIBs should be improved to expand their potential applications. To enhance the safety properties of LIBs, novel pyrrolinium-based ionic liquids (ILs) were proposed as an alternative electrolyte to the current carbonate electrolyte, which have some task-specific functional groups, i.e., a planar C[dbnd]N double bond, a C-O ether linkage, and no unstable C-H bond, designed to improve their electrochemical performances as well as the physicochemical properties. As a result, the pyrrolinium-based ILs exhibited much improved physicochemical and electrochemical properties compared to those of the known ILs. Among the prepared ILs, N-allyl-2-methoxypyrrolinium bis(fluorosulfonyl)imide (A(OMe)Pyrl-FSI, 4) showed the high ionic conductivity (10.2 mS cm?1), the very good cycling performance (99.3% of retention ratio after 50 cycles) with a LiFePO4 electrode, and the much improved lithium ion transference number (0.19). IL 4 also had the remarkable rate capability at 5 C-rate with the retention ratio of 81.2% (124.8 mA h g?1), compared to the initial discharge capacity of 153.7 mA h g?1 at 0.1 C-rate. In addition, both their high thermal stability and non-flammability were also confirmed.
Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates
Knipp, Ralph J.,Estrada, Rosendo,Sethu, Palaniappan,Nantz, Michael H.
supporting information, p. 3422 - 3429 (2014/05/06)
The relative cleavage of an alcohol from a panel of amino esters and amino carbonates via intramolecular cyclization was examined as a mechanism for substrate release. Thermal stability at 37 °C was observed only for the seven-membered ring progenitors. Applicability of the approach was illustrated by δ-lactam formation within a poly(dimethylsiloxane) microchannel for release of a captured fluorescent probe.
Radiosynthesis of 11C-levetiracetam: A potential marker for PET imaging of SV2A expression
Cai, Hancheng,Mangner, Thomas J.,Muzik, Otto,Wang, Ming-Wei,Chugani, Diane C.,Chugani, Harry T.
supporting information, p. 1152 - 1155 (2014/12/10)
The multistep preparation of 11C-levetiracetam (11C-LEV) was carried out by a one-pot radiosynthesis with 8.3 ± 1.6% (n = 8) radiochemical yield in 50 ± 5.0 min. Briefly, the propionaldehyde was converted to propan-1-imine in situ as labeling precursor by incubation with ammonia. Without further separation, the imine was reacted with 11C-HCN to form 11C-aminonitrile. This crude was then reacted with 4-chlorobutyryl chloride and followed by hydrolysis to yield 11C-LEV after purification by chiral high-performance liquid chromatography (HPLC). Both the radiochemical and enantiomeric purities of 11C-LEV were >98%.
[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters
Mamone, Patrizia,Gruenberg, Matthias F.,Fromm, Andreas,Khan, Bilal A.,Goossen, Lukas J.
supporting information; experimental part, p. 3716 - 3719 (2012/09/08)
The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.
REVERSE HEAD GROUP LIPIDS, LIPID PARTICLE COMPOSITIONS COMPRISING REVERSE HEADGROUP LIPIDS, AND METHODS FOR THE DELIVERY OF NUCLEIC ACIDS
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Page/Page column 33, (2011/06/11)
The present invention related to a novel class of zwitterionic lipids that are useful in the preparation of lipid particles suitable for the delivery of encapsulated nucleic acids to cells.
Gold(l)-Catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles
Mukherjee, Paramita,Widenhoeferst, Ross A.
supporting information; experimental part, p. 1184 - 1187 (2010/05/18)
"Chemical Equation Presented" A 1:1 mixture of [P(t-Bu) 2-obiphenyl]AuCl and AgSbF6 catalyzes the intermolecular amination of allylic alcohols with 1-methylimldazolidin-2one and related nucleophiles that, In the case of γ-unsubstituted or γ-methyl- substituted allylic alcohols, occurs with high γ-regioselectivity and syn-stereoselectivlty.
Catalytic, asymmetric vinylogous Mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: How the diene heteroatom impacts stereocontrol
Curti, Claudio,Ranieri, Beatrice,Battistini, Lucia,Rassu, Gloria,Zambrano, Vincenzo,Pelosi, Giorgio,Casiraghi, Giovanni,Zanardi, Franca
supporting information; experimental part, p. 2011 - 2022 (2010/11/17)
Denmark's chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vinylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of d-hydroxylated g-butenolide-type frameworks with high efficiency and valuable margins of regio-, diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol, with syn-configured aldol adducts emerging from pyrroles bearing electron- withdrawing N-protecting groups (Boc, Ts, and Cbz) and anti-configured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.
