Category: 53562-86-0

Ema, Tadashi; Sugiyama, Yasushi; Fukumoto, Minoru; Moriya, Hiroyuki; Cui, Jing-Nan; Sakai, Takashi; Utaka, Masanori published an article about the compound: (S)-Methyl 3-hydroxybutanoate( cas:53562-86-0,SMILESS:C[C@H](O)CC(OC)=O ).Category: piperazines. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:53562-86-0) through the article.

An NADPH-dependent reductase that shows reducing activity for 1-chloro-2-hexanone has been purified from bakers’ yeast. SDS-PAGE and gel filtration suggested that the purified reductase is a monomeric enzyme with a mol. weight of ca. 37 kDa. Asym. reduction of several carbonyl compounds using the purified reductase has been carried out. 1-Chloro-2-hexanone, 1-acetoxy-2-heptanone, Me acetoacetate, Et pyruvate, 1-chloro-2,4-pentanedione, and 2,4-hexanedione were reduced to the corresponding alcs. with high enantiomeric purities (>98% ee). The reductase showed high specificity constants (kcat/Km = 103-105 s-1 M-1) and relatively low Michaelis constants (Km = 10-4-10-3 M) for all the substrates examined

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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Safety of (S)-Methyl 3-hydroxybutanoate. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Highly Effective Chiral Ortho-Substituted BINAPO Ligands (o-BINAPO): Applications in Ru-Catalyzed Asymmetric Hydrogenations of β-Aryl-Substituted β-(Acylamino)acrylates and β-Keto Esters. Author is Zhou, Yong-Gui; Tang, Wenjun; Wang, Wen-Bo; Li, Wenge; Zhang, Xumu.

A novel family of chiral ortho-substituted BINAPO ligands (o-BINAPO) I (R = H, Me, Ph, 3,5-Me2C6H3; R1 = Ph, 3,5-Me2C6H3) were prepared from the corresponding binaphthols and diarylchlorophosphines; complexes of I with [(p-cymene)RuCl2]2 were highly efficient catalysts for asym. hydrogenation of β-aryl-substituted β-(acylamino)acrylates R2C(AcNH):CHCO2R3 (R2 = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 2-MeOC6H4; R3 = Me, Et) and β-aryl-substituted β-keto esters R4COCH2CO2R5 (R4 = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 2-MeOC6H4, Me, ClCH2; R5 = Me, Et) to give nonracemic β-amino acid esters R2CH(NHAc)CH2CO2R3 (R2 = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 2-MeOC6H4; R3 = Me, Et) and β-hydroxy esters R4CH(OH)CH2CO2R5 (R4 = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 2-MeOC6H4, Me, ClCH2; R5 = Me, Et). While most asym. hydrogenation catalysts are effective only with single stereoisomers of β-amidoesters, hydrogenation catalysts prepared from I and [(p-cymene)RuCl2]2 hydrogenated E/Z mixture of β-aryl-substituted β-(acylamino)acrylates enantioselectively to give β-(acetylamino)esters in high enantiomeric excesses. E.g., Me 3-phenyl-3-acetylamino-2-propenoate PhC:NHAcCHCO2Me (prepared from Me 3-phenyl-3-oxopropanoate by addition of ammonium acetate, precipitation, and acylation with acetic anhydride) undergoes enantioselective hydrogenation in ethanol at 80 psi and 50° in the presence of a ruthenium catalyst prepared from I (R = 3,5-Me2C6H3; R1 = Ph) and [(p-cymene)RuCl2]2 to give PhCH(NHAc)CH2CO2Me in 99% ee.

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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

SDS of cas: 53562-86-0. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Influence of Synthesis Conditions on the Structure of Nickel Nanoparticles and their Reactivity in Selective Asymmetric Hydrogenation. Author is Arrigo, Rosa; Gallarati, Simone; Schuster, Manfred E.; Seymour, Jake M.; Gianolio, Diego; da Silva, Ivan; Callison, June; Feng, Haosheng; Proctor, John E.; Ferrer, Pilar; Venturini, Federica; Grinter, David; Held, Georg.

Unsupported and SiO2-supported Ni nanoparticles (NPs) were synthesized via hot-injection colloidal route using oleylamine (OAm) and trioctylphosphine (TOP) as reducing and protective agents, resp. By adopting a multi-length scale(coating process) structural characterization, it was found that by changing equivalent of OAm and TOP not only the size of the nanoparticles is affected but also the Ni electronic structure. The synthesized NPs were modified with (R,R)-tartaric acid (TA) and investigated in the asym. hydrogenation of Me acetoacetate to chiral methyl-3-hydroxy butyrate. The comparative anal. of structure and catalytic performance for the synthesized catalysts has enabled us to identify a Ni metallic active surface, whereby the activity increases with the size of the metallic domains. Conversely, at the high conversion obtained for the unsupported NPs there was no impact of particle size on the selectivity. (R)-selectivity was very high only on catalysts containing pos. charged Ni species such as over the SiO2-supported NiO NPs. This work shows that the chiral modification of metallic Ni NPs with TA is insufficient to maintain high selectivity towards the (R)-enantiomer at long reaction times and provides guidance for the engineering of long-term stable enantioselective catalysts.

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Piperazine – Wikipedia,
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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A new class of versatile chiral-bridged atropisomeric diphosphine ligands: remarkably efficient ligand syntheses and their applications in highly enantioselective hydrogenation reactions, published in 2006-05-03, which mentions a compound: 53562-86-0, mainly applied to chiral bridged diphosphine ligand preparation asym hydrogenation catalyst; iridium chiral bridged diphosphine ligand complex asym hydrogenation catalyst; ruthenium chiral bridged diphosphine ligand asym hydrogenation complex catalyst; ketoester asym hydrogenation beta hydroxy ester preparation; dehydroamino acid asym hydrogenation beta amino acid preparation; intramol Ullmann coupling bisiodoaryl diphosphine dioxide, Quality Control of (S)-Methyl 3-hydroxybutanoate.

A series of chiral diphosphine ligands denoted as PQ-Phos (I, II, and III; n = 0, 1, 2) was prepared by atropdiastereoselective Ullmann coupling and ring-closure reactions. The Ullmann coupling reaction of the biaryl diphosphine dioxides (IV; n = same as above) is featured by highly efficient central-to-axial chirality transfer with diastereomeric excess >99%. This substrate-directed diastereomeric biaryl coupling reaction is unprecedented for the preparation of chiral diphosphine dioxides, and our method precludes the tedious resolution procedures usually required for preparing enantiomerically pure diphosphine ligands. The effect of chiral recognition was also revealed in a relevant asym. ring-closure reaction of (S)- or (R)-HO-BIPHEPO (V) or (VI) with chiral alkanediol dimesylate or ditosylate (VII; R = Ms, n = 0; R = Ts, n = 1 or 2). The chiral tether bridging the two aryl units creates a conformationally rigid scaffold essential for enantiofacial differentiation; fine-tuning of the ligand scaffold (e.g., dihedral angles) can be achieved by varying the chain length of the chiral tether. The enantiomerically pure Ru- and Ir-PQ-Phos complexes have been prepared and applied to the catalytic enantioselective hydrogenations of α- and β-ketoesters (C:O bond reduction) of formula R1COCO2R2 (R1 = Me or Ph, R2 = Me; R1 = Me, iso-Pr, Ph, or PhCH2CH2) and R1COCHR2CO2R3 (R1 = Me, R2 = H, R3 = Me, Et, or CH2Ph; R1 = ClCH2 or Ph, R2 = H, R3 = Et; R1 = Ph, R2 = Cl, R3 = Et) to chiral α- or β-hydroxy esters of formula R1CH(OH)CO2R2 and R1CH(OH)CHR2CO2R3, 2-(6′-methoxy-2′-naphthyl)propenoic acid, alkyl-substituted β-dehydroamino acids (C:C bond reduction) of formula R2O2CCH:C(R1)NHAc (R1 = Me, Et, iso-Pr, or tert-Bu, R2 = me; R1 = Me or n-Pr, R2 = Et) to chiral β-amino acid esters of formula R2O2CCH2CHC(R1)NHAc, and N-heteroaromatic compounds (C:N bond reduction) (VIII; R1 = Me, R2 = Me, H, MeO; R1 = Ph, R2 = H), (IX), and (X) to chiral heterocyclic compounds (XI), (XII), and (XIII). An excellent level of enantioselection (up to 99.9% ee) has been attained for the catalytic reactions. In addition, the significant ligand dihedral angle effects on the Ir-catalyzed asym. hydrogenation of N-heteroaromatic compounds were also revealed.

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Reference:
Piperazine – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-Methyl 3-hydroxybutanoate(SMILESS: C[C@H](O)CC(OC)=O,cas:53562-86-0) is researched.COA of Formula: C9H7NO3. The article 《Process for the stereoselective biotransformation of acetoacetic acid esters using yeasts》 in relation to this compound, is published in Biocatalysis. Let’s take a look at the latest research on this compound (cas:53562-86-0).

A process for the stereospecific reduction of acetoacetic acid esters to the 3-(S)-hydroxybutanoic acid esters by Saccharomyces cerevisiae and Candida utilis grown on glucose and EtOH media was developed. A continuous single stage steady state production system was superior to pulse, batch, and fed-batch systems in terms of optical product purity, biomass concentration, and production rates. Optical purity of 3-(S)-hydroxybutanoic acid esters produced with S. cerevisiae and C. utilis was dependent on pH. Maximum optical purity was obtained at pH 2.2 from S. cerevisiae on EtOH medium. The sp. product formation rates of the chemostat cultures were 0.02-0.05 g/g-h. C. utilis was more productive than S. cerevisiae but it reconsumed the product under c-limited growth conditions.

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Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Related Products of 53562-86-0. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about A strategy for the stereoselective synthesis of unsymmetric atropisomeric ligands: preparation of NAPhePHOS, a new biaryl diphosphine.

MeO-NAPhePHOS (shown as I) represents the 1st example of atropisomeric diphosphines bearing heterotopic biaryl moieties. The key step of its synthesis is the diastereoselective, intramol., CuI-promoted coupling of 1-iodo-2-naphthol and 2-iodo-3-methoxyphenol connected by a chiral tether. (R,R)-2,4-Pentanediol was used as the chiral auxiliary in this highly selective reaction that leads to a single enantiomer of the title diphosphine. In the Ru-promoted hydrogenations of carbonyl derivatives, NAPhePHOS affords enantioselectivity levels fully comparable to those of the C2-sym. analogs, BINAP and MeO-BIPHEP, resp., thus showing that the lack of C2 symmetry is not detrimental to the catalytic properties of atropisomeric ligands in these hydrogenation reactions.

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Piperazine – Wikipedia,
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Rampulla, David M.; Gellman, Andrew J. published an article about the compound: (S)-Methyl 3-hydroxybutanoate( cas:53562-86-0,SMILESS:C[C@H](O)CC(OC)=O ).Electric Literature of C5H10O3. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:53562-86-0) through the article.

Of the three types of chiral surfaces described in this entry, the most well-developed ones are those that are produced by templating with chiral organic modifiers. Although the mechanisms and adsorbate/substrate interactions that impart enantioselectivity on these surfaces are not understood in great detail, some such surfaces have been highly optimized to give highly enantioselective separations and catalytic reactions. Naturally chiral surfaces can be generated from materials that are chiral in bulk, or achiral materials cleaved to expose surface structures that are chiral at the nanoscale. The crystalline nature of these structures makes them good candidates for a detailed study of the origins of enantiospecificity on their surfaces.

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Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Category: piperazines. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Synthesis of BINAP ligands with imidazole tags for highly enantioselective Ru-catalyzed asymmetric hydrogenation of β-keto esters in ionic liquid systems. Author is Jin, Xin; Kong, Fang-fang; Yang, Zhi-qiang; Cui, Fei-fei.

The imidazole-tagged BINAP ligands were synthesized and used for Ru-catalyzed asym. hydrogenation of β-keto esters in ionic liquid (IL) systems. The Ru-BINAP catalysts with the imidazolium tags show high catalytic activity and enantioselectivity, which closely parallel the performance of unmodified BINAP. The catalyst recycling experiments using [bmim]Tf2N/MeOH system demonstrated that introducing imidazolium moieties to the BINAP backbone can effectively enhance the affinity of the Ru-catalysts to the IL, reduce Ru leaching and improve catalysts stability, and after several cycles no significant loss of activity and enantioselectivity was observed

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Piperazine – Wikipedia,
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Synthetic Route of C5H10O3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Stereoselective Synthesis of Premisakinolide A, the Monomeric Counterpart of the Marine 40-Membered Dimeric Macrolide Misakinolide A. Author is Nakamura, Ryoichi; Tanino, Keiji; Miyashita, Masaaki.

The first synthesis of protected premisakinolide A (I), the monomeric counterpart of misakinolide A, the marine 40-membered macrolide displaying potent activity against a variety of human carcinoma cell lines (no data), has been reported. The strategy was highlighted by a crucial coupling of a tetrahydropyran fragment and an alkynylaluminum reagent having a polypropionate chain, the highly stereoselective cross aldol reaction of segment A and segment B, and the stereospecific construction of the polypropionate structure based on original acyclic stereocontrol.

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Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-Methyl 3-hydroxybutanoate(SMILESS: C[C@H](O)CC(OC)=O,cas:53562-86-0) is researched.Application of 54903-09-2. The article 《New chiral phospholanes; synthesis, characterization, and use in asymmetric hydrogenation reactions》 in relation to this compound, is published in Tetrahedron: Asymmetry. Let’s take a look at the latest research on this compound (cas:53562-86-0).

The practical synthesis of enantiomerically pure trans-2,5-disubstituted-1-phenylphospholanes, e.g., I, which are then employed in the preparation of a new series of C2-sym. bis-, e.g., II, and C3-sym. tris(phospholane) ligands, is described. A versatile three-step route to the important chiral 1,4-diol intermediates, e.g., III, used in the phosphine syntheses, is outlined. Rhodium complexes bearing the new phosphine ligands were prepared and shown to act as efficient catalyst precursors for the enantioselective hydrogenation of various unsaturated substrates. The crystal structure of 3 of the prepared Rh complexes were determined

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Piperazine – Wikipedia,
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