Tag: M.W:100-200

Name: (R)-4-Hydroxydihydrofuran-2(3H)-one. 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 Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I: Application of Asymmetric Crotylsilane Bond Constructions.

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

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.Hou, Jinsong; Yang, Gaosheng; Chai, Zhuo researched the compound: 4-Methoxypiperidine( cas:4045-24-3 ).Reference of 4-Methoxypiperidine.They published the article 《Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines》 about this compound( cas:4045-24-3 ) in Journal of Organic Chemistry. Keywords: cyclic amidine preparation diastereoselective; cyanoalkene amine tandem addition cyclization reaction lanthanide catalyst. We’ll tell you more about this compound (cas:4045-24-3).

A tandem insertion of aliphatic nitriles and unactivated alkenes RCH(CN)CH2C(R1)=C(R2)R3 (R = Ph, 2-thienyl, 3-pyridinyl, etc.; R1 = H, Me; R2 = H, Me, Ph, 2-naphthyl, etc.; R3 = H, Me) to the N-H bond of secondary aliphatic amines such as dibenzylamine, pyrrolidine, thiomorpholine, etc. catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines I (R4 = benzyl(methyl)aminyl, tetrahydroisoquinolin-2-yl, thiomorpholin-4-yl, etc.) under mild reaction conditions.

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one(SMILESS: O=C1OC[C@H](O)C1,cas:58081-05-3) is researched.Reference of 4-Methoxypiperidine. The article 《Absolute stereochemistries of the aplysiatoxins and oscillatoxin A》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:58081-05-3).

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

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 Photoredox B-H functionalization to selective B-N(sp3) coupling of nido-carborane with primary and secondary amines, the main research direction is crystal structure mol carborane amino nitrogen containing preparation heterocyclic; photoredox catalyst selective coupling nido carborane primary secondary amine.Quality Control of 4-Methoxypiperidine.

Access to nido-carborane site-selective B-N(sp3) coupling by photoredox catalyzed B-H activation has been achieved for the first time, which leads to the synthesis of a series of nitrogen-containing nido-carboranes with moderate to good yields. This protocol is applicable to primary and secondary amines containing alkyl, or heteroaryl groups as well as sulfonamides. Furthermore, the open to air and metal-free conditions with excellent site-selectivity represent a significant improvement for B-H functionalization of nido-carboranes with organic functionalities.

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

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: 58081-05-3, is researched, Molecular C4H6O3, 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.Recommanded Product: 58081-05-3.

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

Shaw, Megan H.; Shurtleff, Valerie W.; Terrett, Jack A.; Cuthbertson, James D.; MacMillan, David W. C. published an article about the compound: 4-Chloro-2-fluoropyridine( cas:34941-92-9,SMILESS:ClC1=CC(=NC=C1)F ).Quality Control of 4-Chloro-2-fluoropyridine. 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.

The use of sp3 C-H bonds-which are ubiquitous in organic mols.-as latent nucleophile equivalent for transition metal-catalyzed cross-coupling reactions has the potential to substantially streamline synthetic efforts in organic chem. while bypassing substrate activation steps. Through the combination of photoredox-mediated hydrogen atom transfer (HAT) and nickel catalysis, we have developed a highly selective and general C-H arylation protocol that activates a wide array of C-H bonds as native functional handles for cross-coupling. This mild approach takes advantage of a tunable HAT catalyst that exhibits predictable reactivity patterns based on enthalpic and bond polarity considerations to selectively functionalize α-amino and α-oxy sp3 C-H bonds in both cyclic and acyclic systems.

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

Product Details of 58081-05-3. 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 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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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Computed Properties of C5H3ClFN. 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 Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates. Author is Nuhant, Philippe; Allais, Christophe; Chen, Ming Z.; Coe, Jotham W.; Dermenci, Alpay; Fadeyi, Olugbeminiyi O.; Flick, Andrew C.; Mousseau, James J..

A versatile synthesis of 7-azaindoles e. g., I, from substituted 2-fluoropyridines is described. C3-metalation and 1,4-addition to nitroolefins provide substituted 2-fluoro-3-(2-nitroethyl)pyridines. A facile oxidative Nef reaction/reductive amination/intramol. SNAr sequence furnishes 7-azaindolines. Finally, optional regioselective electrophilic C5-substitution (e.g., bromination or nitration) and subsequent in situ oxidation delivers highly functionalized 7-azaindoles in high overall efficiency.

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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: 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, the main research direction is nicotinic acid piperazinyl trifluoromethyl preparation antibacterial; fluoroacetate condensation ethyl trifluoroacetate; pyridone preparation chlorination.Recommanded Product: 52208-50-1.

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.

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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: 4045-24-3, is researched, SMILESS is COC1CCNCC1, Molecular C6H13NOJournal, Article, Angewandte Chemie, International Edition called Amine-Responsive Disassembly of AuI-CuI Double Salts for Oxidative Carbonylation, Author is Cao, Yanwei; Yang, Jian-Gong; Deng, Yi; Wang, Shengchun; Liu, Qi; Shen, Chaoren; Lu, Wei; Che, Chi-Ming; Chen, Yong; He, Lin, the main research direction is amine gold copper salt oxidative carbonylation synergistic catalyst; carbamates; double salts; oxidative carbonylation; synergistic catalysis; urea.Electric Literature of C6H13NO.

A sensitive amine-responsive disassembly of self-assembled AuI-CuI double salts was observed and its use for the synergistic catalysis was enlightened. Study of the disassembly of [Au(NHC)2][CuI2] revealed the contribution of Cu-assisted ligand exchange of N-heterocyclic carbene (NHC) by amine in [Au(NHC)2]+ and the capacity of [CuI2]- on the oxidative step. By integrating the implicative information coded in the responsive behavior and inherent catalytic functions of d10 metal complexes, a catalyst for the oxidative carbonylation of amines was developed. The advantages of this method were clearly reflected on mild reaction conditions and the significantly expanded scope (51 examples); both primary and steric secondary amines can be employed as substrates. The cooperative reactivity from Au and Cu centers, as an indispensable prerequisite for the excellent catalytic performance, was validated in the synthesis of (un)sym. ureas and carbamates.

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