Tag: M.W=50-100

Straker, R. N. published the artcileComputational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Nature Communications (2016), 10109, database is CAplus and MEDLINE.

Many diastereoselective (substrate stereocontrol), and enantioselective (catalyst stereocontrol) cycloisomerizations was developed. However, asym. cycloisomerizations where a chiral catalyst specifies the stereochem. outcome of the cyclization of a single enantiomer substrate-regardless of its inherent preference-were unknown. A combined theor. and exptl. approach enables the design of a highly reactive rhodium catalyst for the stereoselective cycloisomerization of ynamide-vinylcyclopropanes to [5.3.0]-azabicycles was showed. Highly diastereoselective cycloisomerizations using an achiral catalyst, and then explored phosphoramidite-complexed rhodium catalysts in the enantioselective variant, where theor. investigations uncovered an unexpected reaction pathway in which the electronic structure of the phosphoramidite dramatically influences reaction rate and enantioselectivity was established. A marked enhancement of both was observed using the optimal theory-designed ligand, which enabled double stereodifferentiating cycloisomerizations in both matched and mismatched catalyst-substrate settings.

Nature Communications 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 C20H22ClN3O3, Recommanded Product: (R)-Oxiran-2-ylmethanol.

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

Ricciardi, Maria published the artcileGlycidol, a Valuable Substrate for the Synthesis of Monoalkyl Glyceryl Ethers: A Simplified Life Cycle Approach, Related Products of alcohols-buliding-blocks, the publication is ChemSusChem (2017), 10(10), 2291-2300, database is CAplus and MEDLINE.

The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production plant, represents a very promising strategy. Here, we report the synthesis of MAGEs through the reaction of glycidol with alcs. catalyzed by a green homogeneous Lewis acids catalyst, such as Bi^III triflate, under very mild reaction conditions. To evaluate the green potential of the proposed alternative, a simplified life cycle assessment (LCA) approach was followed by comparing the environmental performance of the proposed innovative route to prepare MAGEs with that of the most investigated pathway from glycerol. A considerable reduction of all impact categories considered was observed in our exptl. conditions, suggesting that the glycidol-to-MAGEs route can be a valuable integration to the glycerol-to-MAGEs chain. Thanks to the use of primary data within the LCA model, the results achieved are a very good approximation of the real case.

ChemSusChem 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, Related Products of alcohols-buliding-blocks.

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

Adhikari, Suraj published the artcileLiquid Chromatographic Enantiomeric Separation of Chiral Aliphatic Amines Using 2-Hydroxynaphthaldehyde as a Derivatizing Agent on Polysaccharide-Derived Chiral Stationary Phases, Quality Control of 96-20-8, the publication is Chromatographia (2018), 81(9), 1337-1344, database is CAplus.

A new liquid chromatog. enantiomer separation of chiral amines as 2-hydroxynaphthaldimine derivatives on several coated and immobilized chiral stationary phases (CSPs) derived from polysaccharides is described. 2-Hydroxynaphthaldehyde was introduced as a derivatizing agent for the enantiomeric separation of chiral aliphatic amines under the normal phase conditions, and was found to both enhance detection sensitivity and provide suitable interaction sites for enantiodiscrimination. Cellulose-derived CSPs, in general, exhibited better enantiomeric separation than amylose-derived CSPs. Amongst the examined six covalently bonded and four coated-type CSPs, covalently bonded Chiralpak IC, which contains a cellulose-based chiral selector, showed the best enantioseparation The method was applied to the determination of the enantiomeric purity of com. available (R)- and (S)-leucinol. The enantiomeric impurities of the studied analytes procured from two suppliers are 0.06-1.20%. The developed anal. method was also validated in accordance with ICH guidelines and is enantioselective, sensitive and effective for the enantiomeric separation of chiral aliphatic amines as 2-hydroxynaphthaldimine derivatives under UV detection.

Chromatographia 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, Quality Control of 96-20-8.

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

Morita, Masao published the artcileTotal Syntheses of Perenniporides, Product Details of C3H6O2, the publication is Organic Letters (2015), 17(22), 5634-5637, database is CAplus and MEDLINE.

The total syntheses of perenniporide A (I) and related compounds have been achieved. Starting from 1,3,5-trifluorobenzene, difluorodienone II was obtained by oxidative dearomatization, which served as a platform for the high-pressure cycloaddition and for the introduction of the C3-methoxy group. The synthesis allowed access to the natural congeners III and IV, enabling assignment of the absolute structures of these natural products.

Organic 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, Product Details of C3H6O2.

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

Leroux, Yves published the artcileReaction of magnesium with γ- and δ-halogenated ketones; synthesis of cyclanols, COA of Formula: C5H10O, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1967), 265(25), 1472-4, database is CAplus.

The reaction of Mg with γ- and δ-halo ketones in tetrahydrofuran (THF) was investigated. Treatment of γ-chlorinated ketones with Mg in THF followed by hydrolysis gave the corresponding pinacols. Similar treatment of γ-brominated ketones at 25° gave the corresponding I (R, R1, R2 and m.p. of phenylurethane derivative given): Me, H, H, 140°; Me, Me, H, 110°; Me, Et, H, 81°; Me, H, Me, 110°; Et, H, H, 125°; Pr, H, H, 99°; Bu, H, H, 95°; pentyl, H, H, 74°. The second alc. above was 60:40 cis-trans mixture and the fourth was practically pure cis isomer. Similar treatment of a δ-bromo ketone, e.g. 1-bromo-5-hexanone, gave 65% 1-methyl-1-cyclopentanol, as well as small amounts of pinacol and non-brominated ketones. The reaction is pictured as involving a radical cleavage of C-halogen bond and a reduction of the carbonyl group to an anion radical.

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques 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

Hill, E. Alexander published the artcileRing cleavage rearrangement of cyclobutylmethylboranes, Computed Properties of 20117-47-9, the publication is Journal of Organometallic Chemistry (1982), 239(2), 279-92, database is CAplus.

Boranes prepared by hydroborating methylenecyclobutane (I) with BH₃-THF, 9-borabicyclo[3.3.1]nonane, and BH₃-Me₂S rearranged on heating at 100-160° to open chain structures. Products after oxidation were the unrearranged cyclobutylmethanol, and 4-penten-1-ol (II), 1,4-pentanediol (III) and 1,5-pentanediol (IV). II was the major product when stoichiometric alkene:BH bonds was used; III and IV were formed with excess BH₃. The rate of rearrangement using BH₃-Me₂S at 100° in triglyme was not significantly dependent upon the initial I-BH₃ ratio (3/1 or 1.15/1) or the presence of excess Me₂S. However, an equivalent amount of pyridine prevented rearrangement. Rearrangement in THF using BH₃-THF also occurred at comparable rates in the presence and absence of excess BH₃. Little or no isomerization of the B function into the cyclobutane ring was observed A concerted 4-center mechanism requiring a vacant B orbital was suggested.

Journal of Organometallic 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, Computed Properties of 20117-47-9.

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

Kapustina, N. I. published the artcileOxidation of 1-methylcyclobutanol with lead(IV) and manganese(III) compounds, Quality Control of 20117-47-9, the publication is Izvestiya Akademi Nauk, Seriya Khimicheskaya (1992), 2760-3, database is CAplus.

1-Phenyl-4-pentanone is formed as the main product of reaction between 1-methylcyclobutanol (I) and Pb(OAc)₄ in benzene. Oxidation of I with Mn(OAc)₃ in AcOH leads to a mixture of Me Pr ketone and 2,9-decanedione. Reaction of I with Pb(OAc)₄ or Mn(OAc)₃ in the presence of a metal halide yields selectively the corresponding 1-substituted (chloro, bromo, thiocyano or cyano) 4-pentanone.

Izvestiya Akademi Nauk, Seriya Khimicheskaya 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, Quality Control of 20117-47-9.

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

Rodrigalvarez, Jesus published the artcileCatalytic C(sp³)-H bond activation in tertiary alkylamines, Formula: C4H11NO, the publication is Nature Chemistry (2020), 12(1), 76-81, database is CAplus and MEDLINE.

The development of robust catalytic methods to assemble tertiary alkylamines provides a continual challenge to chem. synthesis. In this regard, transformation of a traditionally unreactive C-H bond, proximal to the nitrogen atom, into a versatile chem. entity would be a powerful strategy for introducing functional complexity to tertiary alkylamines. A practical and selective metal-catalyzed C(sp³)-H activation facilitated by the tertiary alkylamine functionality, however, remains an unsolved problem. Here, we report a Pd(II)-catalyzed protocol that appends arene feedstocks to tertiary alkylamines via C(sp³)-H functionalization. A simple ligand for Pd(II) orchestrates the C-H activation step in favor of deleterious pathways. The reaction can use both simple and complex starting materials to produce a range of multifaceted γ-aryl tertiary alkylamines and can be rendered enantioselective. The enabling features of this transformation should be attractive to practitioners of synthetic and medicinal chem. as well as in other areas that use biol. active alkylamines.

Nature 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, Formula: C4H11NO.

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

Twum, Elvis A. published the artcileInitial development of a cytotoxic amino-seco-CBI warhead for delivery by prodrug systems, COA of Formula: C3H6O2, the publication is Bioorganic & Medicinal Chemistry (2015), 23(13), 3481-3489, database is CAplus and MEDLINE.

Cyclopropabenzaindoles (CBIs) are exquisitely potent cytotoxins which bind and alkylate in the minor groove of DNA. They are not selective for cancer cells, so prodrugs are required. CBIs can be formed at physiol. pH by Winstein cyclisation of 1-chloromethyl-3-substituted-5-hydroxy-2,3-dihydrobenzo[e]indoles (5-OH-seco-CBIs). Corresponding 5-NH₂-seco-CBIs should also undergo Winstein cyclisation similarly. A key triply orthogonally protected intermediate on the route to 5-NH₂-seco-CBIs has been synthesized, via selective monotrifluoroacetylation of naphthalene-1,3-diamine, Boc protection, electrophilic iodination, selective allylation at the trifluoroacetamide and 5-exo radical ring-closure with TEMPO. This intermediate has potential for introduction of peptide prodrug masking units (deactivating the Winstein cyclisation and cytotoxicity), addition of diverse indole-amide side-chains (enhancing non-covalent binding prior to alkylation) and use of different leaving groups (replacing the usual chlorine, allowing tuning of the rate of Winstein cyclisation). This key intermediate was elaborated into a simple model 5-NH₂-seco-CBI with a dimethylaminoethoxyindole side-chain. Conversion to a bio-reactive entity and the bioactivity of this system were confirmed through DNA-melting studies (ΔT_m = 13 °C) and cytotoxicity against LNCaP human prostate cancer cells (IC₅₀ = 18 nM).

Bioorganic & Medicinal 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 C6H20Cl2N4, COA of Formula: C3H6O2.

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

Moriyama, Mizuki published the artcileDivergent asymmetric total synthesis of all four pestalotin diastereomers from (R)-glycidol, Related Products of alcohols-buliding-blocks, the publication is Molecules (2020), 25(2), 394, database is CAplus and MEDLINE.

All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asym. Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal derived from (R)-glycidol produced a syn-aldol adduct with high diastereoselectivity and enantioselectivity using a Ti(iOPr)₄/(S)-BINOL/LiCl catalyst. Diastereoselective Mukaiyama aldol reactions mediated by catalytic achiral Lewis acids directly produced not only a (1’S,6S)-pyrone precursor via the syn-aldol adduct using TiCl₄, but also (1’S,6R)-pyrone precursor via the antialdol adduct using ZrCl₄, in a stereocomplementary manner. A Hetero-Diels-Alder reaction of similarly available mono(TMSO)diene (Brassard’s diene) with (S)-2-benzyloxyhexanal produced the (1’S,6S)-pyrone precursor promoted by Eu(fod)₃ and the (1’S,6R)-pyrone precursor Et₂AlCl. Debenzylation of the (1’S,6S)-precursor and the (1’S,6R)-precursor furnished natural (-)-pestalotin (99% ee, 7 steps) and unnatural (+)-epipestalotin (99% ee, 7 steps), resp. Mitsunobu inversions of the obtained (-)-pestalotin and (+)-epipestalotin successfully produced the unnatural (+)-pestalotin (99% ee, 9 steps) and (-)-epipestalotin (99% ee, 9 steps), resp., in a divergent manner. All four of the obtained chiral pestalotin diastereomers possessed high chem. and optical purities (optical rotations, 1H-NMR, 13C-NMR, and HPLC measurements).

Molecules 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, Related Products of alcohols-buliding-blocks.

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