Tag: M.W=50-100

Xu, Shibo published the artcileNickel-Catalyzed Regio- and Stereospecific C-H Coupling of Benzamides with Aziridines, Application of 2-Aminobutan-1-ol, the publication is Organic Letters (2021), 23(14), 5471-5475, database is CAplus and MEDLINE.

A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines was disclosed. The current strategy provided direct access to benzolactams by the C-H alkylation-intramol. amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines was controlled by the substituents. The reaction with chiral aziridines proceeded with inversion of configuration, thus suggesting an SN²-type nucleophilic ring-opening pathway.

Organic Letters published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C11H24O3, Application of 2-Aminobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Brady, Stephen F. published the artcileSome novel, acid-labile amine protecting groups, SDS of cas: 20117-47-9, the publication is Journal of Organic Chemistry (1977), 42(1), 143-6, database is CAplus and MEDLINE.

RO2C-Phe-OH [I; R = cyclopropylmethyl (CP), 1-methylcyclobutyl (MCB), cyclobutyl, 1-methylcyclohexyl, 1-cyclopropylethyl] and R1O2C-Phe-Ala-OMe (R1 = CP, MCB) were prepared After 48 hr in 50% HOAc, >99% of MCBO2C-Phe-OH (II) remained unchanged, whereas under the same conditions 10-15% of BOC was cleaved from BOC-Phe-OH. However, the complete removal of MCBO2C was achieved by treating II with CF3CO2H at 25° for 30 min. ROH were treated with COCl2 to give RO2CCl which were treated with phenylalanine or with H-Phe-OMe and saponified to give I.

Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, SDS of cas: 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gential, Geoffroy P. P. published the artcileSynthesis and evaluation of fluorescent Pam₃Cys peptide conjugates, HPLC of Formula: 57044-25-4, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(15), 3641-3645, database is CAplus and MEDLINE.

Chirally pure R- and S-epimers of TLR2 ligand Pam₃CysSK₄ were prepared and sep. conjugated to an OVA model epitope, in which lysine was replaced by azidonorleucine. The azide function in the conjugate permitted labeling with different fluorophores by use of strain-promoted 3+2 cycloaddition The R-epimer of the labeled conjugates induced TLR2-dependent DC maturation, while S-epimer proved to be inactive. Combining the lipophilicity of Pam₃CysSK₄ ligand with fluorophores influenced the solubility of the resulting conjugates in an unpredictable way and only the conjugates labeled with Cy-5 were suitable for confocal fluorescence microscopy experiments It was shown that both epimers of the Cy-5 labeled lipopeptides were internalized equally well, indicating TLR2-independent cellular uptake. The presented results demonstrate the usefulness of strain-promoted azide-alkyne cycloaddition in the labeling of highly lipophilic lipopeptides without disturbing the in vitro activity of these conjugates with respect to activation of TLR-2.

Bioorganic & Medicinal Chemistry Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, HPLC of Formula: 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liu, Jia published the artcileAphadilactones A-D, four diterpenoid dimers with DGAT inhibitory and antimalarial activities from a Meliaceae plant, Name: (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2014), 79(2), 599-607, database is CAplus and MEDLINE.

Aphadilactones A-D isolated from Aphanamixis grandifolia (Meliaceae) are 4 diastereoisomers with an unprecedented carbon skeleton. Their challenging structures and absolute configurations were determined by a combination of spectroscopic data, chem. degradation, fragment synthesis, exptl. CD spectra, and ECD calculations The aphadilactones A-D and their oxidative products were tested for DGAT inhibitory activities in vitro. Aphadilactone C with the 5S,11S,5’S,11’S configuration had potent and selective inhibition against diacylglycerol O-acyltransferase-1 (DGAT-1; IC₅₀ = 0.46 μM; selectivity index >217). Thus, aphadilactone C is the strongest natural DGAT-1 inhibitor discovered to date. The aphadilactones A-D also had significant antimalarial activities against Plasmodium falciparum with in vitro IC₅₀ values of 190, 1350, 170, and 120 nM, resp.

Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Name: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Creary, Xavier published the artcileγ-Trimethylsilylcyclobutyl Carbocation Stabilization, COA of Formula: C5H10O, the publication is Journal of Organic Chemistry (2015), 80(3), 1781-1788, database is CAplus and MEDLINE.

Isomeric 3-trimethylsilyl-1-arylcyclobutyl carbocations, where the cross-ring 3-trimethylsilyl group has the potential to interact with the cationic center, were generated under solvolytic conditions. When the cationic center can interact with the rear lobe of the carbon-silicon bond, rate enhancements become progressively larger as the substituent on the aryl group becomes more electron-withdrawing. When the potential interaction with the trimethylsilyl group is via a front lobe interaction, there is minimal rate enhancement over the range of substituents. Computational studies also were carried out on these cations. Calculated trimethylsilyl stabilization energies progressively increase with electron-withdrawing character of the aryl groups when the trimethylsilyl interaction is via the rear lobe. But there are minimal changes in stabilization energies when the potential trimethylsilyl interaction is via the front lobe of the carbon-silicon bond. These computational studies, along with the solvolytic studies, point to a significant rear lobe 3-trimethylsilyl stabilization of arylcyclobutyl cations. They also argue against any front lobe stabilization of the isomeric arylcyclobutyl cations.

Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, COA of Formula: C5H10O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Willwacher, Jens published the artcileTotal Synthesis, Stereochemical Revision, and Biological Reassessment of Mandelalide A: Chemical Mimicry of Intrafamily Relationships, Product Details of C3H6O2, the publication is Chemistry – A European Journal (2015), 21(29), 10416-10430, database is CAplus and MEDLINE.

Mandelalide A and three congeners had recently been isolated as the supposedly highly cytotoxic principles of an ascidian collected off the South African coastline. Since these compounds are hardly available from the natural source, a concise synthesis route was developed, targeting one structure as the purported representation of mandelalide A. The sequence involves an iridium-catalyzed two-directional Krische allylation and a cobalt-catalyzed carbonylative epoxide opening as entry points for the preparation of the major building blocks. The final stages feature the first implementation of terminal acetylene metathesis into natural product total synthesis, which is remarkable in that this class of substrates had been beyond the reach of alkyne metathesis for decades. Synthetic mandelalide A, however, proved not to be identical with the natural product. In an attempt to clarify this issue, NMR spectra were simulated for 20 conceivable diastereomers by using DFT followed by DP4 anal.; however, this did not provide a reliable assignment either. The puzzle was ultimately solved by the preparation of three diastereomers, of which one compound proved identical with mandelalide A in all anal. and spectroscopic regards. As the entire northern sector about the THF ring in that compound shows the opposite configuration of what had originally been assigned, it is highly likely that the stereostructures of the sister compounds mandelalides B-D must be corrected analogously; we propose that these natural products are accurately represented by addnl. structures. In an attempt to prove this reassignment, an entry into mandelalides C and D was sought by subjecting an advanced intermediate of the synthesis of 6 to a largely unprecedented intramol. Morita-Baylis-Hillman reaction, which furnished the γ-lactone derivative 74 as a mixture of diastereomers. Whereas (24R)-74 was amenable to a hydroxyl-directed dihydroxylation by using OsO₄/TMEDA as the reagent, the sister compound (24S)-74 did not follow a directed path but simply obeyed Kishi’s rule; only this unexpected escape precluded the preparation of mandelalides C and D by this route. A combined spectroscopic and computational (DFT) study showed that the reasons for this strikingly different behavior of the two diastereomers are rooted in their conformational peculiarities. This aspect apart, our results show that the OsO₄/TMEDA complex reacts preferentially with electron deficient double bonds even if other alkenes are present that are more electron rich and less encumbered. Finally, in a brief biol. survey authentic mandelalide A was found to exhibit appreciable cytotoxicity only against one out of three tested human cancer cell lines and all synthetic congeners were hardly active. No significant fungicidal properties were observed The proposed new structure was (1R,3R,4E,6Z,9R,10R,12R,13R,15R,18E,21S,23R)-23-[(6-deoxy-2-O-methyl-α-L-mannopyranosyl)oxy]-13-hydroxy-15-(hydroxymethyl)-3,10-dimethyl-16,25,26-trioxatricyclo[19.3.1.1^9,12]hexacosa-4,6,18-trien-17-one for mandelalide A.

Chemistry – A European Journal published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C15H20O6, Product Details of C3H6O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kurogome, Yuji published the artcileSynthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation, Quality Control of 57044-25-4, the publication is Synthesis (2016), 48(5), 765-771, database is CAplus.

Stereoselective synthesis of decytospolide A and B (I and II, resp.) and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2-naphthoates was optimized to give products with a 2,6-cis-tetrahydropyran ring with high diastereoselectivity and yield.

Synthesis published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Withall, David M. published the artcileStereochemistry and Mechanism of Undecylprodigiosin Oxidative Carbocyclization to Streptorubin B by the Rieske Oxygenase RedG, Application In Synthesis of 57044-25-4, the publication is Journal of the American Chemical Society (2015), 137(24), 7889-7897, database is CAplus and MEDLINE.

The prodiginines are a group of specialized metabolites that share a 4-methoxypyrrolyldipyrromethene core structure. Streptorubin B is a structurally remarkable member of the prodiginine group produced by Streptomyces coelicolor A3(2) and other actinobacteria. It is biosynthesized from undecylprodigiosin by an oxidative carbocyclization catalyzed by the Rieske oxygenase-like enzyme RedG. Undecylprodigiosin derives from the RedH-catalyzed condensation of 2-undecylpyrrole and 4-methoxy-2, 2′-bipyrrole-5-carboxaldehyde (MBC). To probe the mechanism of the RedG-catalyzed reaction, we synthesized 2-(5-pentoxypentyl)-pyrrole, an analog of 2-undecylpyrrole with an oxygen atom next to the site of C-C bond formation, and fed it, along with synthetic MBC, to Streptomyces albus expressing redH and redG. This resulted in the production of the 6′-oxa analog of undecylprodigiosin. In addition, a small amount of a derivative of this analog lacking the n-pentyl group was produced, consistent with a RedG catalytic mechanism involving hydrogen abstraction from the alkyl chain of undecylprodigiosin prior to pyrrole functionalization. To investigate the stereochem. of the RedG-catalyzed oxidative carbocyclization, [7′-²H](7’R)-2-undecylpyrrole and [7′-²H](7’S)-2-undecylpyrrole were synthesized and fed sep., along with MBC, to S. albus expressing redH and redG. Anal. of the extent of deuterium incorporation into the streptorubin B produced in these experiments showed that the pro-R hydrogen atom is abstracted from C-7′ of undecylprodigiosin and that the reaction proceeds with inversion of configuration at C-7′. This contrasts sharply with oxidative heterocyclization reactions catalyzed by other nonheme iron-dependent oxygenase-like enzymes, such as isopenicillin N synthase and clavaminate synthase, which proceed with retention of configuration at the carbon center undergoing functionalization.

Journal of the American Chemical Society published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C13H26N2, Application In Synthesis of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ghosh, Kousik published the artcileA triple alkoxo bridged dinuclear cobalt(III) complex mimicking phosphatase and showing ability to degrade organic dye contaminants by photocatalysis, COA of Formula: C4H11NO, the publication is Journal of Organometallic Chemistry (2019), 52-64, database is CAplus.

A dinuclear Co(III) complex, [(N₃)L¹Co^IIIL²Co^IIIL¹] (1), was synthesized and characterized {H₂L¹ = 2-((1-hydroxybutan-2-ylimino)methyl)-4-bromophenol and HL² = 2-amino-1-butanol}. Single crystal x-ray diffraction anal. confirmed its structure. Extended supra-mol. architectures were generated in the complex through weak noncovalent interactions. The energetic features of significant supramol. interactions were studied using DFT calculation and further corroborated with NCI plot index computational tool. The complex was found to mimic the role of phosphatase enzyme efficiently by transforming 4-nitrophenylphosphate to 4-nitrophenolate at room temperature The reaction follows Michaelis-Menten enzymic reaction kinetics with turnover numbers of ∼1.4 s^-1 in aqueous DMF (98% DMF, volume/volume) medium. The complex also acts as an efficient photocatalyst for degradation of organic pollutants. Methylene blue (MB), a widely used dye in various industries, was selected as a model pollutant in aqueous media to evaluate the photocatalytic effectiveness of the complex.

Journal of Organometallic Chemistry published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, COA of Formula: C4H11NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Karpati, Levente published the artcileThe sequenced structure of amino-alcohol-based random poly(ester amide)s, Recommanded Product: 2-Aminobutan-1-ol, the publication is Journal of Thermal Analysis and Calorimetry (2019), 136(2), 737-747, database is CAplus.

Random amino-alc.-based poly(ester amide)s were synthesized using adipic acid and differently substituted amino-alcs., namely 2-amino-ethan-1-ol, 1-amino-propan-2-ol, 2-amino-butan-1-ol and 2-amino-2-methyl-propan-1-ol. The effect of substitution on the yield and fine structure was investigated using residual functional group anal., SEC and NMR. The functional group anal. and SEC proved the blocking effect of small substituents on direct polycondensation. The NMR data suggested a sequenced structure that could cause the formation of different crystalline phases in linear amino-alc.-based poly(ester amide)s. Three different crystalline phases with different thermal stability and crystallization rate were observed with DSC and WAXS. The crystalline nature of the poly(ester amide)s proves the sequenced organization along the backbone.

Journal of Thermal Analysis and Calorimetry published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, Recommanded Product: 2-Aminobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts