Heterocyclic Building Blocks-Pyrrolines

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 52208-50-1, is researched, Molecular C5H2Cl2FN, about New synthesis method of 2,6-dichloro-3-fluoropyridine, the main research direction is dichloro fluoropyridine nitrification catalytic hydrogenation reduction diazotization.Formula: C5H2Cl2FN.

2, 6-Dichloro-3-nitropyridine was synthesized from 2, 6-dichloropyridine by nitrification reaction. Then 2,6-dichloro-3-aminopyridine was synthesized from 2,6-dichloro-3-nitropyridine by the catalytic hydrogenation reduction reaction. At last, 2,6-dichloro-3-fluoropyridine was synthesized from 2,6-dichloro-3-aminopyridine by the diazotization reaction. Overall yield of three steps reaction was 69.3%. The target compound was confirmed by MS and NMR. The factors such as nitric acid concentration, the type and amount of catalyst and the molar ratio of sodium nitrite were discussed in detail. This synthesis route has high yield, high selectivity, and better prospect of industrialization.

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

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.Du, Xiao-Ming; Sun, Ning-Yi; Irino, Nobuto; Shoyama, Yukihiro researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Quality Control of (R)-4-Hydroxydihydrofuran-2(3H)-one.They published the article 《Glycosidic constituents from in vitro Anoectochilus formosanus》 about this compound( cas:58081-05-3 ) in Chemical & Pharmaceutical Bulletin. Keywords: glycoside Anoectochilus structure. We’ll tell you more about this compound (cas:58081-05-3).

The glycosidic constituents of whole plants of Anoectochilus formosanus propagated by tissue culture were investigated. A new compound, 2-(β-D-glucopyranosyloxymethyl)-5-hydroxymethylfuran, along with the known compounds, 3-(R)-3-β-D-glucopyranosyloxybutanolide (kinsenoside), 3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid, 1-O-isopropyl-β-D-glucopyranoside, (R)-(+)-3,4-dihydroxybutanoic acid γ-lactone, 4-(β-D-glucopyranosyloxy)benzyl alc., (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside, and corchoionoside C were isolated.

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

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 Single-step conversion of chiral carnitine and derivatives into (S)- and (R)-β-substituted γ-butyrolactones, published in 1997-01-31, which mentions a compound: 58081-05-3, mainly applied to butyrolactone preparation; carnitine cyclocondensation, Safety of (R)-4-Hydroxydihydrofuran-2(3H)-one.

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

Moore, Richard E.; Blackman, Adrian J.; Cheuk, Chad E.; Mynderse, Jon S.; Matsumoto, Gayle K.; Clardy, Jon; Woodard, Ronald W.; Craig, J. Cymerman published the article 《Absolute stereochemistries of the aplysiatoxins and oscillatoxin A》. Keywords: absolute configuration aplysiatoxin oscillatoxin; NMR proton aplysiatoxin oscillatoxin; CD aplysiatoxin oscillatoxin; crystal structure aplysiatoxin.They researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Synthetic Route of C4H6O3. 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.

CD and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallog. anal. of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asym. carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochem. at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).

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

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, 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, which mentions a compound: 58081-05-3, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3, Recommanded Product: 58081-05-3.

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

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines, Author is Patil, Dilip V.; Si, Tengda; Kim, Hun Young; Oh, Kyungsoo, which mentions a compound: 4045-24-3, SMILESS is COC1CCNCC1, Molecular C6H13NO, Electric Literature of C6H13NO.

The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddn. reaction of N-nitrosoamines to alkenes, e.g., 1H-Indene was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines, e.g., 1,4-dioxa-8-azaspiro[4.5]decane to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives e.g., I were obtained in a one-pot tandem N-nitrosation and photoaddn. sequence.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. 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, the main research direction is hydroxybutanolide preparation appetite depressant; butanolide hydroxymethyl hydroxy appetite stimulant; hunger modulator hydroxybutanolide.COA of Formula: C4H6O3.

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

Safety of (R)-4-Hydroxydihydrofuran-2(3H)-one. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Total syntheses of oscillatoxin D and 30-methyloscillatoxin D. Author is Toshima, Hiroaki; Goto, Takashi; Ichihara, Akitami.

The first total syntheses of oscillatoxin D and 30-methyloscillatoxin D have been accomplished. The construction of the spiroether has been achieved by intramol. Michael-type addition as a key step based on a possible biomimetic pathway.

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

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

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.

If you want to learn more about this compound((R)-4-Hydroxydihydrofuran-2(3H)-one)Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(58081-05-3).

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