Category: pyrrolines

Calvisi, Giuseppina; Catini, Roberto; Chiariotti, Wilma; Giannessi, Fabio; Muck, Sandra; Tinti, Maria Ornella; De Angelis, Francesco published the article 《Single-step conversion of chiral carnitine and derivatives into (S)- and (R)-β-substituted γ-butyrolactones》. Keywords: butyrolactone preparation; carnitine cyclocondensation.They researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).HPLC of Formula: 58081-05-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:58081-05-3) here.

An efficient 1-step conversion of chiral carnitine and its derivatives into stereoisomerically pure (S)- and (R)-β-substituted γ-butyrolactones by cyclocondensation is described. (S)- or (R)-carnitine and (R)-aminocarnitine give β-hydroxy-γ-butyrolactone and β-amino-γ-butyrolactone in 82 and 77% yield, resp., with retention. (R)-(acetylamino)carnitine gives (R)-β-acetylamino-γ-butyrolactone in 90% yield, while (R)-acetylcarnitine gives 2(5H)-furanone under the same reaction conditions in 77% yield via cyclization and subsequent elimination. (R)-N-benzyloxycarnitinamide gives a mixture of pyrrolidinone (11% yield) and furanoyl imidate (50% yield) derivatives

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Electric Literature of C4H6O3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about A novel synthesis of (R)- and (S)-4-hydroxytetrahydrofuran-2-ones. Author is Tanaka, Akira; Yamashita, Kyohei.

The hydroxy ester I (R = H, R1 = OH), prepared from L-ascorbic acid by sequential treatment with acetone and AcCl, 30% H2O2 and CaCO3, and Me2SO4, was treated with MeSO2Cl and pyridine in CH2Cl2 to give 90% I (R = H, R1 = MeSO3), which, when heated at 85° with LiCl in DMF furnished a mixture of the erythro and threo chloro esters I (R = Cl, R1 = H; R = H, R1 = Cl) (II). Upon hydrogenolysis with 10% Pd/C in the presence of Et3N, II yielded the ester I (R = R1 = H), which was treated with dilute HCl giving a nearly quant. yield of hydroxylactone III. The (S)-enantiomer was analogously prepd from D-isoascorbic acid.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Chloro-2-fluoropyridine(SMILESS: ClC1=CC(=NC=C1)F,cas:34941-92-9) is researched.Recommanded Product: 27328-68-3. The article 《The reactivity of 2-fluoro- and 2-chloropyridines toward sodium ethoxide: Factors governing the rates of nucleophilic (het)aromatic substitutions》 in relation to this compound, is published in Helvetica Chimica Acta. Let’s take a look at the latest research on this compound (cas:34941-92-9).

The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25° were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF3 group increases the reactivity more than single halogen atoms do, whatever the element, and the latter are superior to Me3Si groups. Substituents accommodated at the 4-position operate through their inductive effect, whereas at the 3-position, this action may be attenuated by steric hindrance. Almost all 5-substituents enhance the rate of the nucleophilic substitution occurring at the 2-position. The sole exception concerns the F-atom at the 5-position which retards the reaction, presumably by lone-pair/lone-pair repulsion with the neg. charge building up at the central C-atom of the intermediate Meisenheimer complex. The substituent effects are additive. Therefore, by using the increments derived from the present work, the rates of future reactions should be predictable with fair accuracy.

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Pyrroline – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature, the main research direction is tertiary butoxycarbonyl amine preparation green chem; amine alc carbon monoxide tertiary butyloxycarbonylation gold copper catalyst; N-tert-butyloxycarbonylation; amines; gold catalysis; homogeneous catalysis; synergistic effect.Category: pyrrolines.

Herein, a step- and atom-economic synthesis of N-Boc amines RC(O)OC(CH3)3 (R = diethylaminyl, piperidin-1-yl, 4-methylpiperazin-1-yl, 1,4-dioxa-8-azaspiro[4.5]decan-8-yl, etc.) from amines RH, t-butanol, and CO was reported at room temperature Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, com. available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implemented and, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcs. R1OH (R1 = t-Bu, 2-methylbutan-2-yl, Bn, etc.). Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

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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 Discovery of a Novel and Brain-Penetrant O-GlcNAcase Inhibitor via Virtual Screening, Structure-Based Analysis, and Rational Lead Optimization, published in 2021-01-28, which mentions a compound: 4045-24-3, mainly applied to GlcNAcase inhibitor screening preparation tauopathy structure, Safety of 4-Methoxypiperidine.

O-GlcNAcase (OGA) has received increasing attention as an attractive therapeutic target for tau-mediated neurodegenerative disorders; however, its role in these pathologies remains unclear. Therefore, potent chem. tools with favorable pharmacokinetic profiles are desirable to characterize this enzyme. Herein, we report the discovery of a potent and novel OGA inhibitor, compound 5i, comprising an aminopyrimidine scaffold, identified by virtual screening based on multiple methodologies combining structure-based and ligand-based approaches, followed by sequential optimization with a focus on ligand lipophilicity efficiency. This compound was observed to increase the level of O-GlcNAcylated protein in cells and display suitable pharmacokinetic properties and brain permeability. Crystallog. anal. revealed that the chem. series bind to OGA via characteristic hydrophobic interactions, which resulted in a high affinity for OGA with moderate lipophilicity. Compound 5i could serve as a useful chem. probe to help establish a proof-of-concept of OGA inhibition as a therapeutic target for the treatment of tauopathies.

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Pyrroline – Wikipedia,
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Name: 4-Chloro-2-fluoropyridine. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Chloro-2-fluoropyridine, is researched, Molecular C5H3ClFN, CAS is 34941-92-9, about One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol. Author is Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao.

A novel method for preparation of aryl cyclopropyl ethers I [Ar = 1-ClC6H4, 2-O2NC6H4, 4-chloro-2-pyridyl, etc.] via nucleophilic aromatic substitution reaction (SNAr) of fluoroarom. compounds with cyclopropanol under relatively mild conditions was developed. The reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroarom. compounds were employed as substrates for a test that proved a wide application scope of the method.

If you want to learn more about this compound(4-Chloro-2-fluoropyridine)Name: 4-Chloro-2-fluoropyridine, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(34941-92-9).

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Pyrroline – Wikipedia,
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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 58081-05-3, is researched, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3Journal, Journal of Agricultural and Food Chemistry called Identification of Novel Glycosidic Aroma Precursors in Saffron (Crocus sativus L.), Author is Straubinger, Markus; Bau, Brigitte; Eckstein, Susanne; Fink, Margit; Winterhalter, Peter, the main research direction is saffron aroma precursor carotenoid metabolite glycoside; glucopyranoside carotenoid metabolite saffron aroma precursor.COA of Formula: C4H6O3.

The methanolic extract of saffron was separated with the aid of multilayer coil countercurrent chromatog. After purification by HPLC, the following seven novel carotenoid metabolites were identified on the basis of their spectral (UV, FTIR, MS, NMR, CD) data: (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde O-β-D-gentiobioside (1), (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarboxylic acid O-β-D-glucopyranoside (2), 6-hydroxy-3-(hydroxymethyl)-2,4,4-trimethylcyclohexa-2,5-dienone 6-O-β-D-glucopyranoside (3), (2Z)-3-methylpent-2-enedioic acid 1-[1-(2,4,4-trimethyl-3,6-dioxocyclohexenyloxy)-O-β-D-glucopyranosid-6-yl] ester (4), (5S)-5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one O-β-D-glucopyranoside (5), (1R,5S,6R)-5-(hydroxymethyl)-4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one O-β-D-glucopyranoside (6), and (1R)- 3,5,5-trimethylcyclohex-3-enol O-β-D-glucopyranoside (7).

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Pyrroline – Wikipedia,
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Name: (R)-4-Hydroxydihydrofuran-2(3H)-one. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Synthesis of (S)- and (R)-3-hydroxy-4-butanolide and (2S,4S)-, (2R,4S)-, (2S,4R)-, and (2R,4R)-2-hydroxy-4-(hydroxymethyl)-4-butanolide and their satiety and hunger modulating activities. Author is Uchikawa, Osamu; Okukado, Nobuhisa; Sakata, Toshiie; Arase, Koichi; Terada, Kenji.

Two endogenous γ-lactones, 3-hydroxy-4-butanolide (I) and 2-hydroxy-4-hydrtoxymethyl-4-butanolide (II) have been identified as substances that enhance, resp., satiety and hunger by their effects on the feeding behavior and the central neurons of rats. All the stereoisomers of these two lactones were synthesized and their effects on the feeding behavior and humoral factors were assessed by infusion into the rat third cerebroventricle. Among four isomers, (2S,4S)-II was most effective in eliciting the feeding and caused potent hypoglycemia with hyperinsulinemia. (S)-I suppressed the food intake more potently than the antipode and caused humoral responses reciprocal to those of (2S,4S)-II. Thus, (S)-I and (2S,4S)-II are physiol. active forms for conveying intrinsic signals of satiety and hunger to neurons in the hypothalamus.

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Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Pharmacologically active compounds in the Anoectochilus and Goodyera species. Author is Du, Xiao-Ming; Irino, Nobuto; Furusho, Norihiro; Hayashi, Jun; Shoyama, Yukihiro.

The extract of Anoectochilus formosanus showed significant activity in decreasing the levels of the cytosolic enzymes LDH, GOT, and GPT, and the result demonstrated that A. formosanus possessed prominent hepatoprotective activity against CCl4-induced hepatotoxicity. Moreover, in the results of the test using aurothioglucose-induced obese mice, the extract showed a significant antihyperliposis effect. A. formosanus grown in the wild and propagated by tissue culture contain ten compounds, including a major known component, (3R)-3-(β-D-glucopyranosyloxy)butanolide (kinsenoside; 1), and two new components, (3R)-3-(β-D-glucopyranosyloxy)-4-hydroxybutanoic acid (2) and 2-[(β-D-glucopyranosyl-oxy)methyl]-5-hydroxymethylfuran (3), along with the known compounds, isopropyl-β-D-glucopyranoside (4), (R)-3,4-dihydroxybutanoic acid γ-lactone (5), 4-(β-D-glucopyranosyloxy) benzyl alc. (6), (6R,9S)-9-(β-D-glucopyranosyloxy)megastigma-4,7-dien-3-one (7), and (3R)-3-(β-D-glucopyranosyloxy)-4-hydroxybutanolide (8). Since a higher concentration of kinsenoside (1) was detected in the crude drugs A. formosanus and A. koshunensis by high-performance liquid chromatog. (HPLC) anal., we proved a simple purification system for kinsenoside (1), giving 180 mg of kinsenoside (1) from 1 g of dried samples for further pharmacol. experiments In an anti-hyperliposis assay using high-fat-diet rats, 1 significantly reduced the weights of the body and the liver, and also decreased the triglyceride level in the liver compared to those of control rats. On the other hand, the epimer of 1, (3S)3-(β-D-glucopyranosyloxy)butanolide, goodyeroside A (9), which was isolated from the Goodyera species, had no effect for anti-hyperliposis. In aurothioglucose-induced obese mice, 1 suppressed the body and liver weight increase, significantly ameliorated the triglyceride level in the liver, and also reduced the deposition of uterine fat pads. The anti-hepatoxic activities of 9 and goodyerosides B (10) were studied on injury induced by CCl4 in primary cultured rat hepatocytes by measuring the levels of LDH, GOT, and GPT. In the CCl4-treated control group, there were marked increases in LDH, GOT, and GPT activities compared with the normal group. In contrast, these levels were suppressed in 9- and 10-treated groups. Goodyerin (11), a new typical flavone glycoside, exhibited a significant and dose-dependent sedative and anticonvulsant effect.

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Pyrroline – Wikipedia,
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Name: 2,6-Dichloro-3-fluoropyridine. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2,6-Dichloro-3-fluoropyridine, is researched, Molecular C5H2Cl2FN, CAS is 52208-50-1, about Preparation of new 2-chloro-5-fluoro-6-[(4-phenylmethyl)piperazinyl]-4-trifluoromethyl-3-nicotinic acid. Author is Remuzon, Philippe; Bouzard, Daniel; Jacquet, Jean Pierre.

The nicotinic acid (I), which could be a key intermediate for novel potential antibacterial 1,8-naphthyridine-3-carboxylic acid analogs, was prepared starting with construction of the pyridine nucleus of II by Et 2-fluoroacetate and Et 2-trifluoroacetate.

There is still a lot of research devoted to this compound(SMILES：ClC1=NC(=CC=C1F)Cl)Name: 2,6-Dichloro-3-fluoropyridine, and with the development of science, more effects of this compound(52208-50-1) can be discovered.

Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem