Month: March 2022

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 Studies on proton pump inhibitors. I. Synthesis of 8-[(2-benzimidazolyl)sulfinyl]-5,6,7,8-tetrahydroquinolines and related compounds, published in 1989-06-30, which mentions a compound: 27231-36-3, mainly applied to benzimidazolylsulfinyltetrahydroquinoline preparation antisecretory antiulcer; structure activity benzimidazolylsulfinyltetrahydroquinoline, Related Products of 27231-36-3.

Many 8-[(2-benzimidazolyl)sulfinyl]-5,6,7,8-tetrahydroquinolines were synthesized and examined for their (H+ + K+) ATPase ATPase-inhibitory and antisecretory activities. These sulfinyl compounds could be considered to be rigid analogs of the 2-[(2-pyridyl)methylsulfinyl]benzimidazole class of antisecretory agents. All the compounds tested were potent inhibitors of (H+ + K+)ATPase. Most of the compounds also inhibited histamine-induced gastric acid secretion in rats. Among them, 8-[(5-fluoro-2-benzimidazolyl)sulfinyl]-3-methyl-5,6,7,8-tetrahydroquinoline (I) was found to have the most potent activity. The structure-activity relationships are discussed.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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.Gerten, Anthony L.; Stanley, Levi M. researched the compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole( cas:503538-69-0 ).COA of Formula: C38H24F4O4P2.They published the article 《Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters》 about this compound( cas:503538-69-0 ) in Organic Chemistry Frontiers. Keywords: indole azomethine ylide copper difluorphos catalyst dearomative cycloaddition; pyrroloindoline enantioselective diastereoselective preparation. We’ll tell you more about this compound (cas:503538-69-0).

Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles were reported. The dearomative cycloaddition reactions occurred in the presence of a catalyst generated in situ from Cu(OTf)2 and (R)-Difluorphos to form exo’-pyrroloindoline cycloadducts and established four contiguous stereogenic centers, two of which were fully substituted. The exo’-pyrroloindoline products were formed in moderate-to-good yields (39-85%) with high diastereoselectivities (up to 98 : 1 : 1 dr) and enantioselectivities (up to 96% ee).

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

SDS of cas: 503538-69-0. 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: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Rhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives.

Enantioselective Rh-promoted activation and 1,4-positional swap of unactivated tetraorganosilanes, e.g., 1-ethyl-3-methyl-3-(2-(trimethylsilyl)phenyl)cyclobutanol (I) to give (1S,3S)-1-ethyl-3-methyl-3((trimethylsilyl)methyl)indanol (II). E.g., reaction of silylphenyl tert-cyclobutanol I with 2.5 mol% [Rh(cod)OH]2/6.0 mol% (R)-Difluorphos ligand at 100° in mesitylene gave 82% yield of trans-indanol II (97% ee).

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Quality Control of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole. 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)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Enantioselective synthesis of fully benzenoid single and double carbohelicenes via gold-catalyzed intramolecular hydroarylation. Author is Satoh, Masakazu; Shibata, Yu; Tanaka, Ken.

The enantioselective synthesis of fully benzenoid single and double carbo[6]helicenes was achieved via the gold-catalyzed intramol. hydroarylation. The single crystal of the racemic double carbo[6]helicene consists of unique layer structures like timbers with halving joints in the woodworking. Furthermore, the double carbo[6]helicenes exhibited relatively large circularly polarized luminescence (CPL) activities among chiral small organic mols.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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 Characterization of volatile compounds in three commercial Chinese vinegars by SPME-GC-MS and GC-O, published in 2019-09-30, which mentions a compound: 3194-15-8, mainly applied to vinegar volatile compound SPME GCMS GCO, Electric Literature of C7H8O2.

Headspace solid-phase microextraction (HS-SPME) coupled with gas chromatog.-mass spectrometry (GC-MS) and gas chromatog.-olfactometry (GC-O) were carried out to qual. and quant. characterize the volatiles and aroma-active compounds in three com. Chinese vinegars, including Zhengrong Rice Vinegar (ZRV), Zhenjiang Aromatic Vinegar (ZAV), and Longmen Smoked Vinegar (LSV). With the aid of DVB/CAR/PDMS fiber, a total of 75 volatile compounds were identified. Among them, 42 aromas were confirmed by their corresponding authentic chems. After comparison of the identified volatiles between the three vinegars, the ZAV sample was found to contain more alcs. and acids, the ZRV sample had more esters and phenols, while the LSV sample was shown to have more identified compounds in the ketones, aldehydes, and pyrazines. In regard to the quantitation, the volatiles that were found in high concentrations included acetic acid (at 14.64, 31.95 and 194 mg/L), furfural (at 5.49, 43.81 and 33.01 mg/L) and tetra-Me pyrazine (at 10.39, 13.51 and 19.41 mg/L) in ZRV, ZAV and LSV, resp. Moreover, thirty volatiles were identified by GC-O as aroma-active compounds that made contributions to the resp. flavor profiles of the com. Chinese vinegar. Eighteen of them were recognized as contributors for all the three com. Chinese vinegars under this study.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 1,4,7,10,13-Pentaoxa-16-azacyclooctadecane(SMILESS: O1CCOCCOCCOCCOCCNCC1,cas:33941-15-0) is researched.Formula: C11H9N. The article 《Selective Phase Transfer Reagents (OxP-crowns) for Chromogenic Detection of Nitrates Especially Ammonium Nitrate》 in relation to this compound, is published in Chemistry – A European Journal. Let’s take a look at the latest research on this compound (cas:33941-15-0).

Nitrogen and phosphorus-containing ions such as ammonium, nitrates and phosphates are anthropogenic pollutants while ammonium nitrate may be diverted for nefarious purposes in improvised explosive devices. Crown ether-oxoporphyrinogen conjugates (OxP-crowns) are used to selectively detect nitrates, especially their ion pairs with K+ and NH4+, based on ion pair complexation of OxP-crowns under phase transfer conditions. The presence of phosphate and carbonate lead to deprotonation of OxP-crowns. OxP-1N18C6 is capable of extracting ion pairs with nitrate from aqueous phase leading to a selective chromogenic response. Deprotonation of the OxP moiety leads to [OxP-]-1N18C6[K+] and is promoted by crown ether selective cation binding coupled with hydration of basic oxoanions, which are constrained to remain in the aqueous phase. This work illustrates the utility of mol. design to exploit partitioning and ion hydration effects establishing the selectivity of the chromogenic response.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Quality Control of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Copper(I)-catalyzed dearomative (3 + 2) cycloaddition of 3-nitroindoles with propargylic nucleophiles: a straightforward access to cyclopenta[b]indolines. Author is Ling, Johanne; Mara, David; Roure, Baptiste; Laugeois, Maxime; Vitale, Maxime R..

The copper(I)-catalyzed dearomatization of 3-nitroindoles with propargylic nucleophiles is described. In mild reaction conditions, this original dearomative (3 + 2) cycloaddition process gives access to a wide variety of cyclopenta[b]indolines in good to excellent yields, with high functional group tolerance. Furthermore, an enantioselective version of this reaction is reachable by employing chiral phosphorous ligands. A mechanism proposal is given, based on kinetic studies.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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, Journal of the American Chemical Society called Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex, Author is Du, Yao; Xu, Li-Wen; Shimizu, Yohei; Oisaki, Kounosuke; Kanai, Motomu; Shibasaki, Masakatsu, which mentions a compound: 503538-69-0, SMILESS is FC1(F)OC2=CC=C(P(C3=CC=CC=C3)C4=CC=CC=C4)C(C5=C6OC(F)(F)OC6=CC=C5P(C7=CC=CC=C7)C8=CC=CC=C8)=C2O1, Molecular C38H24F4O4P2, Category: benzoxazole.

A highly diastereoselective reductive Mannich coupling of ketimines and α,β-unsaturated esters was developed using CuOAc-PPh3 or CuOAc-MePPh2 complex as a catalyst (5 mol %) and pinacolborane as a reducing reagent. The reaction was easily conducted at room temperature, and the substrate generality was broad. This platform methodol. was extended to the first catalytic asym. reductive Mannich reaction of ketimines using CuOAc-DIFLUORPHOS as the catalyst (10 mol %). Switching the reducing reagent from pinacolborane to (EtO)3SiH was key to inducing the high enantioselectivity (82-93% ee). High diastereoselectivity was also maintained (3:1∼30:1). Thus, products containing contiguous tetra- and trisubstituted carbons were catalytically synthesized with high stereoselectivities. Products were converted to α,β,β-trisubstituted (β2,3,3) amino acid derivatives without any racemization and epimerization through simple treatment under acidic conditions. This method is the first entry of the catalytic asym. synthesis of β2,3,3-amino acid derivatives, which constitute important chiral building blocks of biol. significant mols.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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 Furan compounds. V. Preparation and configuration of furyl ketoximes, published in 1958, which mentions a compound: 3194-15-8, mainly applied to , Name: 1-(Furan-2-yl)propan-1-one.

cf. C.A. 45, 5676i. Several pairs of syn- and anti-furyl ketoximes were prepared, characterized, and their configuration established chem. and by UV absorption spectra determinations NaOH (100 g.) in 110 mL. H2O stirred with cooling with 86.9 g. HONH2.HCl in 220 mL. H2O and the mixture stirred 3 h. at 25-30° with 110 g. 2-furyl Me ketone, 2-RC4H3O (I) (R = Ac), the solution treated with 200 mL. saturated NH4Cl solution and the product washed with H2O yielded 80% anti-2-furyl Me ketoxime, anti-2-RC4H3O (II) (R = MeC:NOH) (IIa), m. 104°; HCl salt, m. 85-90°. IIa (10 g.) in 250 mL. Et2O at 0° saturated with dry HCl until the initial precipitate redissolved and the solution kept overnight, evaporated in vacuo and the residue washed with 2N Na2CO3, filtered and the precipitate recrystallized (H2O) gave 6.5 g. syn-IIa, m. 74°; HCl salt, m. 128-9°. Syn-IIa (1 g.) in 10 mL. 2N H2SO4 at 80° kept overnight at room temperature, neutralized with 2N Na2CO3, and the product crystallized (alc.) gave 0.6 g. anti-IIa. Furan (102 g.) and 390.4 g. (EtCO)2O at 40° treated in 5 min. with 15 mL. 85% H3PO4 and the mixture stirred 1 h. at 60-5°, the cooled mixture neutralized with 600 mL. 50% KOH and extracted repeatedly with Et2O, the extract dried (Na2SO4) and evaporated yielded 72% I (R = EtCO) (Ia), b11 74-5°. NaOH (50 g.) in 150 mL. H2O stirred with cooling with 43.5 g. HONH2.HCl in 150 mL. H2O and the mixture treated dropwise with 62.1 g. Ia at 25-30°, the mixture stirred 3 h. and the solution treated with 120 mL. saturated NH4Cl solution, the solidified product filtered off and taken up in 180 mL. alc., the filtered solution chilled, and diluted with 400 mL. H2O gave 35 g. pure anti-II (R = EtC:NOH) (IIb), m. 73°. Working up the mother liquor yielded 23 g. impure anti-IIb, m. 48-50°. Conversion of anti-IIb through the HCl salt in Et2O and crystallization of the crude product (dilute alc.) yielded 83% authentic syn-IIb, m. 77-8°. HONH2.HCl (46 g.), 56.2 g. anhydrous NaOAc, and 94.6 g. I (R = Bz) refluxed 1 h. in 550 mL. absolute alc. and the solution filtered hot, the residue washed with 140 mL. absolute alc. and the filtrate and washings kept 2 days, filtered, and the product recrystallized (EtOAc) yielded 23% anti-II (R = PhC:NOH) (IIc), m. 161°. Concentration of the mother liquor and treatment of the isomeric mixture (72 g., m. 132-5°) with HCl in Et2O yielded 96% syn-IIc, m. 149° (dilute alc.). Ac2O (510 g.) and 205.3 g. α-methylfuran treated as above with 25 g. 85% H3PO4 yielded 38% 5-methyl-2-furyl Me ketone (III), b12 78-80°. III (115 g.) in 650 mL. alc. and 77.6 g. HONH2.HCl in 240 mL. H2O containing 95.4 g. anhydrous NaOAc kept 16 h. and evaporated in vacuo with passage of 400-50 mL. alc., the concentrate diluted with 1 l. H2O and the solution chilled, 1 h. filtered, and the crystalline product (117 g.) recrystallized (400 mL. C6H6 and 100 mL. C6H6) gave 66 g. pure anti-5-methyl-2-furyl Me ketoxime (anti-IV), m. 83°. Concentration of the 2 mother liquors and treatment with HCl in Et2O yielded 88% syn-IV, m. 109°. HONH2.HCl (69.5 g.) in 120 mL. H2O and 100 g. NaOH in 120 mL. H2O added to a hot solution of 111 g. 2-benzofuryl Ph ketone (V) (cf. Stoermer, et al., C.A. 18, 2160) in 2 l. MeOH and the mixture boiled 20 min., concentrated and the residue treated with 750 mL. H2O and 250 mL. saturated NH4Cl solution, the precipitate taken up in a min. of alc., and the filtered solution diluted with H2O gave 111 g. isomeric mixture of anti- and syn-2-benzofuryl Ph ketoxime (anti-VI and syn-VI) (VII). VII (53.4 g.) shaken with 267 mL. Ac2O and the solution kept 1 day, filtered from 10.6 g. anti-VI acetate (VIa), m. 146°, and the filtrate diluted with 2 volumes ice H2O, neutralized with solid Na2CO3, and the solid product (50 g.) recrystallized (alc. and EtOAc) gave 18.9 g. VIa. VIa (20 g.) heated in 200 mL. 2N NaOH and the cooled solution diluted with 200 mL. H2O, stirred with 85 mL. saturated NH4Cl solution and filtered, the precipitate washed with H2O and dried in vacuo, taken up in a min. of warm PhMe and the filtered solution treated with petr. ether, the crude oxime (11.7 g., m. 140-53°) taken up in hot alc., and the solution diluted with H2O gave 10 g. anti-VI, m. 156°. Rearrangement of VII or pure anti-VI with HCl in Et2O gave syn-VI, m. 145° (dilute MeOH). anti-2-Benzofuryl Me ketoxime (anti-VIII), m. 154-5° (cf. C.A. 44, 2973d), rearranged yielded 84% syn-VIII, m. 161°. The oximes shaken with 10 volumes Ac2O and the solutions kept 3 h., poured into ice H2O, and neutralized with Na2CO3 gave the acetates. The oximes (0.01 mol) in 10 mL. C5H5N acetylated with equivalent amounts of BzCl or p-MeC6H4SO2Cl at -5 to -10°, kept 1 h. at 0° and poured into ice H2O, filtered, and the precipitate washed with H2O and dried over H2SO4 and KOH gave the benzoates and tolylsulfonates [oxime, and m.p. (solvent of crystallization) of acetate, benzoate, and tolylsulfonate given]: syn-IIa, 75° (H2O), 84° (petr. ether), 88° (C6H6-petr. ether); anti-IIb, 94° (petr. ether), 93° (petr. ether), 68°; anti-IIc, 109-10° (petr. ether), 144° (EtOAc), 84° (Me2CO-H2O); syn-IIc, 68° (petr. ether), 99-100° (alc.), 118°; anti-IV, 66° (petr. ether), 86° (petr. ether), 72° (decomposition) (C6H6-petr. ether); syn-IV, 94° (petr. ether), 95° (petr. ether), 112°; anti-VIII, 95-6° (petr. ether), 135-6° (alc.), 100-2°; syn-VIII, 77° (petr. ether), 90° (petr. ether), 140° (Me2COH2O); anti-VI, 146°, 152° (alc.), 116-18° (C6H6-petr. ether); syn-VI, 81° (alc.), 120° (alc.), 112° (C6H6-petr. ether). Anti-VI (10.2 g.) in 20 mL. C5H5N treated gradually at -5 to -10° with 9 g. r-MeC6H4SO2Cl and the mixture kept 1 h. at 0°, poured into 150 mL. ice H2O and the oily product triturated with Me2CO, the trituration diluted with H2O and filtered, and the precipitate washed with 2N HCl and H2O gave 15.25 g. anti-VI p-toluenesulfonate, m. 116-18° (Me2CO-ice H2O and C6H6-petr. ether). The preparation of the pairs of ketoximes permitted for the 1st time a systematic comparative spectroscopic examination UV absorption spectra for furfural oxime (IX), IIa, IIb, and IV showed a single maximum at 270 mμ, IIc had 2 maximum, and the spectra of VI and VIII were complicated. The syn- and anti-isomers showed a small difference in wave length but a larger difference in intensity. Based on the established configuration of IX, the chem. assigned configurations were spectroscopically confirmed. The preferential formation of anti-isomers in alk. media and of isomeric mixtures in neutral or acid media and the mechanism of the rearrangement in ethereal HCl were discussed.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Formula: C7H8O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-(Furan-2-yl)propan-1-one, is researched, Molecular C7H8O2, CAS is 3194-15-8, about New Components with Potential Antioxidant and Organoleptic Properties, Detected for the First Time in Liquid Smoke Flavoring Preparations. Author is Guillen, Maria D.; Ibargoitia, Maria L..

A com. aqueous smoke preparation was exhaustively extracted, using dichloromethane as solvent, until the carrier had totally lost its smoky odor. Qual. and quant. characterizations of the extract were performed by means of gas chromatog./mass spectrometry and gas chromatog. with flame ionization detector, resp. Carbonyl derivatives including aldehydes and ketones as well as acids and esters are almost absent; however, the high proportion of phenol, guaiacol, and syringol derivatives is noticeable. The presence of di-tert-butylhydroxytoluene, several hopanes, and a number of lignin dimers must be pointed out; these latter components had apparently not been detected before either in smoke flavorings or in wood smoke. The mass spectral data of the compounds considered as lignin dimers and of the unidentified components are given. The presence of lignin dimers is very interesting from the point of view of health and food technol. for their therapeutic, organoleptic, and antioxidant properties.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem