Heterocyclic Building Blocks-Pyrrolines

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; Irino, Nobuto; Furusho, Norihiro; Hayashi, Jun; Shoyama, Yukihiro researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Name: (R)-4-Hydroxydihydrofuran-2(3H)-one.They published the article 《Pharmacologically active compounds in the Anoectochilus and Goodyera species》 about this compound( cas:58081-05-3 ) in Journal of Natural Medicines. Keywords: Anoectochilus hepatoprotectant lipid lowering Goodyera hepatotoxicity obesity. We’ll tell you more about this compound (cas:58081-05-3).

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

Computed Properties 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 Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I: Application of Asymmetric Crotylsilane Bond Constructions. Author is Masse, Craig E.; Yang, Michael; Solomon, Jason; Panek, James S..

A highly convergent asym. synthesis of the ansamycin antibiotics (+)-mycotrienin I (I) [R = 2-(S)-cyclohexylcarbonylaminopropionyl] and (+)-mycotrienol I (R = H) has been achieved through the synthesis and coupling of the C9-C16 subunit II and the aromatic subunit III, resp. This article describes the complete details of that work as it illustrates the utility of our developing chiral (E)-crotylsilane bond construction methodol. in total synthesis. All four stereogenic centers were introduced using chiral allylsilane bond construction methodol. In the synthesis of subunit II, the C12 and C13 stereocenters were installed using an asym. crotylsilylation reaction to α-keto dibenzyl acetal MeCOCH(OCH2Ph)2. The C11 stereocenter was subsequently installed via a chelate-controlled addition of allyltrimethylsilane to establish the anti-1,3-diol system. The C14-C15 trisubstituted double bond was then installed via a reductive opening of α,β-unsaturated lactone (IV). Aromatic subunit III was chosen on the basis of its synthon equivalency to the amidobenzoquinone system of I. Subunit III was constructed in a concise six-step sequence which incorporates the C3 stereogenic center of the C1-C5 side chain. The C3 stereogenic center was established using a Weinreb amidation of 2,5-dimethoxy-3-phenylsulfonylmethylaniline with (+)-3R-methoxybutanolide, whose absolute stereochem. was derived using the crotylsilane methodol. The union of subunit II with aromatic subunit III was accomplished using a sulfone-based coupling strategy. Coupling product (V) was transformed through a sequence of steps to triene. Divergence from this advanced intermediate allows access to both natural products. The successful completion of the synthesis included the incorporation of the (E,E,E)-triene unit with simultaneous macrocyclization through a palladium (0)-catalyzed (Stille-type) coupling macrocyclization.

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

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 C4H6O3Conference, Asymmetric Catalysis on Industrial Scale called Production of chiral C3 and C4 units via microbial resolution of 2,3-dichloro-1-propanol, 3-chloro-1,2-propanediol and related halohydrins, Author is Kasai, Naoya; Suzuki, Toshio, the main research direction is microbial resolution fermentation chiral.Product Details of 58081-05-3.

The study and development of microbial methods for the industrial-scale production of C3 and C4 chiral synthetic units such as 2,3-dichloro-1-propanol (DCP), epichlorohydrin (EP), 3-chloro-1,2-propanediol (CPD), glycidol (GLD), 4-chloro-3-hydroxy-butyrate (CHB), 3-hydroxy-γ-butyrolactone (HL) is described. The following points are emphasized: overall strategy; screening, isolation, and cultivation of bacteria; control of fermentation reactions; and transfer from lab- to production-scale.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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: 34941-92-9, is researched, SMILESS is ClC1=CC(=NC=C1)F, Molecular C5H3ClFNJournal, Article, Angewandte Chemie, International Edition called C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols, Author is Maligres, Peter E.; Li, Jing; Krska, Shane W.; Schreier, John D.; Raheem, Izzat T., the main research direction is palladium catalyst alkoxylation aryl heteroaryl halide alc; aromatic ether preparation.HPLC of Formula: 34941-92-9.

The authors describe a Pd/Josiphos catatyst system for alkoxylation of activated aryl and heteroaryl halides with primary, secondary, and select tertiary alcs. E.g., in presence of [Pd2(dba)3] and ligand CyPF-tBu (I), C-O cross-coupling of 4-chloro-2-methylquinoline and PhCH2CH2OH gave 99% aromatic ether 4-(2-phenylethoxy)-2-methylquinoline.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao published an article about the compound: 4-Chloro-2-fluoropyridine( cas:34941-92-9,SMILESS:ClC1=CC(=NC=C1)F ).HPLC of Formula: 34941-92-9. 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:34941-92-9) through the article.

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.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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

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

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, Article, Research Support, Non-U.S. Gov’t, Brain Research Bulletin called Structural and stereoisomeric specificity of serum-borne sugar acids related to feeding control by rats, Author is Sakata, Toshiie, the main research direction is sugar acid appetite hypothalamus structure.Quality Control of (R)-4-Hydroxydihydrofuran-2(3H)-one.

Specificity of chem. structures and stereoisomers among serum-borne short-chain organic acids in rats were assessed for their effects on feeding behavior and humoral factors by infusion into the rat 3rd cerebroventricle. Infusion of glyceric acid (1.0 μmol), 3,4-dihydroxybutanoic acid γ-lactone (3,4-DB), or 3,4,5-trihydroxypentanoic acid γ-lactone (2.50 μmol) immediately before the dark phase decreased food intake for, at most, 24 h. These acids did not affect drinking or ambulation. Initial feeding, not necessarily accompanied by periprandial drinking, was induced after infusion of 2,4-dihydroxy-butanoic acid γ-lactone, 2,4,5-trihydroxypentanoic acid γ-lactone (2,4,5-TP), or exogenous 2,4,5,6-tetrahydroxyhexanoic acid γ-lactone (2.50 μmol) in the light phase. Of these acids, 3,4-DB most potently suppressed and 2,4,5-TP most potently enhanced feeding. Of these, the 2S,4S-isomer and the 3S-isomer were the most potent of 2,4,5-TP and 3,4-DB, resp. Only the 2S,4S-isomer of 2,4,5-TP induced hypoglycemia with hyperinsulinemia, whereas opposite effects were produced by the 3S-isomer of 3,4-DB. The positions of the hydroxyl groups on 4-butanolide and the S- and S,S-stereoisomers are important in modulating food intake through the hypothalamus.

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

Formula: C4H6O3. 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: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Intensified crystallization in complex media: Heuristics for crystallization of platform chemicals.

This paper presents heuristics for the integration of fermentation with the appropriate crystallization based in-situ product recovery (ISPR) technique. Here techniques, such as co-crystallization (CC), evaporative crystallization (EC), template induced crystallization (TIC), cooling crystallization (ClC) and electrochem. induced crystallization (EIC), that were recently developed or applied to fermentations were evaluated. For this purpose, the operating windows of fermentation and crystallization of the top-twelve platform chems. as identified by the US Department of Energy were extracted from literature and processed. The results show that in principle all mols. can be crystallized and confirm that different classes of platform chems. require different crystallization techniques. Finally, the results show that intensified crystallization, by means of utilizing external fields (EIC) or tunable solid state properties (CC), seems to be a very feasible ISPR technique.

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