Tag: M.W=50-100

Sanceau, Jean-Yves published the artcileTotal Synthesis of the Antidiabetic (Type 2) Lipid Mediator Protectin DX/PDX, Name: (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2019), 84(2), 495-505, database is CAplus and MEDLINE.

The first total synthesis of a lipid mediator derived from natural ω-3-fatty acid docosahexaenoic acid (DHA), 10S,17S-diHDHA (also referred to as protectin DX/PDX), was achieved in a convergent route (29 steps). The two chiral hydroxyl groups at C-10 and C-17 were derived from readily available (S)-1,2,4-butanetriol and (R)-glycidol, resp. The two stereodefined E-double bonds were generated by a Takai olefination, and the skipped diene side chain was introduced with a stereocontrolled Wittig olefination. Importantly, the sensitive conjugated E,Z,E-triene intermediate was generated by a Boland reduction of the central triple bond of a E,E-dienyne. Overall, this synthetic strategy should allow the preparation of a larger quantity of PDX, which is inaccessible via previously reported biosynthetic approaches.

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

Dickman, John published the artcileMass spectrometry in structural and stereochemical problems. CLXIX. Determination of the structures of the ions produced in the single and double McLafferty rearrangements by ion cyclotron resonance spectroscopy, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1969), 91(8), 2069-84, database is CAplus.

Two possible structural isomers of the C3H6O•+ ion produced by electron impact induced fragmentations are the keto ion Me2CO+• and the enol ion MeC(:CH2)O+H•. The electron impact induced double Mc-Lafferty rearrangement can also produce a C3H6O•+ ion which could conceivably exist in either the enol or sym. oxonium ion structure. Ion cyclotron resonance and pulsed double resonance spectroscopy are used to study the ion-mol. reactions of the keto species, generated from acetone; the enol species, generated from 2-hexanone (via a McLafferty rearrangement) and from 1-methylcyclobutanol; and the double McLafferty species, generated from 5-nonanone. Seven ion-mol. reactions are found which distinguish between the keto and enol ions, thus substantiating the proposed differences in structure. In all cases studied, the enol ion, from 2-hexanone and the enol ion from 1-methylcyclobutanol behave identically indicating their structures to be equivalent The same ion-mol. reactions which distinguish between the keto and enol isomers can be utilized to distinguish between the keto and double McLafferty species. The enol and double McLafferty species react identically in all systems studied thus suggesting identical structures and raising serious doubts about the earlier proposed existence of a sym. double McLafferty oxonium ion. Deuterium labeling is employed to distinguish between isomeric ions of identical mass.

Journal of the American Chemical Society 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, Category: alcohols-buliding-blocks.

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

Shu, Chao published the artcilePhotoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals, Quality Control of 20117-47-9, the publication is Organic Letters (2020), 22(18), 7213-7218, database is CAplus and MEDLINE.

A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are conveniently prepared by radical-mediated ring-opening of cyclic alcs. and hemiacetals, resp. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue-light can initiate a radical chain mechanism.

Organic Letters 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 C8H6ClNO, Quality Control of 20117-47-9.

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

Tomic, L. published the artcileTris(dipivaloyemethanato)holmium induced NMR shifts, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is Croatica Chemica Acta (1971), 267-9, database is CAplus.

The NMR of 1-methylcyclobutanol and 1-octanol were studied by means of complexes of Ho and Pr with 2,2,6,6-tetramethyl-3,5-heptanedione (DPM). The complex Ho(DPM)3 is a more powerful NMR shift reagent than Eu(DPM)3 and Pr(DPM)3, but introduces considerably stronger line broadening, spin-spin splittings being observable only for the most distant protons from the coordination site.

Croatica Chemica Acta 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 C17H18N2O6, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Siewert, Riko published the artcileNon-covalent interactions in molecular systems: thermodynamic evaluation of the hydrogen bond strength in aminoalcohols, Recommanded Product: 2-Aminobutan-1-ol, the publication is Physical Chemistry Chemical Physics (2021), 23(44), 25226-25238, database is CAplus and MEDLINE.

In mols. with two functional groups that form hydrogen bonds, the structure-property relationship can depend significantly on the strength of intra-mol. hydrogen bonding. This bonding can cause a substantial conformational change that is accompanied by a frequency shift in the IR spectrum, which provides the basis for exptl. studies. Despite its great importance in biol. systems, the available literature data for the strength of this bonding are scarce and not in agreement. In this work, we present the results of four thermodn. methods for the determination of the strength of intramol. hydrogen bonds. Comprehensive thermochem. anal. of 1-amino-2-alcs. and 2-amino-1-alcs. was performed with Fourier-transform IR spectroscopy, high-level G4 quantum-chem. calculations, the homomorph scheme with enthalpies of vaporization and a group contribution method. With the combination of these four thermodn. methods, the strength of intramol. hydrogen bonding in 1,2-aminoalcs. and 2,1-aminoalcs. was evaluated quant. The results were correlated with NBO parameters to find an explanation for the different strengths of intramol. hydrogen bonds in total charge transfer and second order stabilization energies.

Physical Chemistry Chemical Physics 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 C7H14N4, Recommanded Product: 2-Aminobutan-1-ol.

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

Tsarev, Vasily N. published the artcileP-chiral monodentate diamidophosphites – New and efficient ligands for palladium-catalysed asymmetric allylic substitution, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is European Journal of Organic Chemistry (2004), 2214-2222, database is CAplus.

Monodentate hexahydropyrrolodiazaphosphole ligands I [R = MeO, Me₂CHO, Me₃CO, (F₃C)₂CHO, 1-Me-1-cyclobutoxy, 1-adamantyloxy, (-)-menthyloxy, PhO, Et₂N, 1-piperidinyl] are prepared and used as ligands for enantioselective allylic substitution and amination reactions of 1,3-diphenylallyl acetate with sodium 4-methylbenzenesulfinate, benzylamine, and di-Me malonate to give substitution products in up to 97% ee. Reaction of alcs. or amines with I (R = Cl) [prepared in one step from (2R)-2-(phenylaminomethyl)pyrrolidine and PCl₃] yields I [R = MeO, Me₂CHO, Me₃CO, (F₃C)₂CHO, 1-Me-1-cyclobutoxy, 1-adamantyloxy, (-)-menthyloxy, PhO, Et₂N, 1-piperidinyl]. I are isolated as mixtures of epimers at phosphorus favoring the (R^P)-configuration. Dinaphthodioxaphosphepines derived from (R)-BINOL are also prepared as nonracemic ligands for comparison. Dimeric rhodium complexes and a monomeric rhodium complexes are prepared from I and [Rh(CO)₂Cl]₂ and characterized by ³¹P NMR. (allyl)palladium complexes derived from I and allylpalladium chloride dimer are prepared as catalysts for allylic substitution and amination reactions; the complexes can also be generated in situ using either allylpalladium chloride dimer or tris(dibenzylideneacetone)dipalladium as precursors, but in some cases the use of in situ generated catalysts gives products with decreased enantioselectivities. The most effective catalysts are those containing phosphine ligands with moderate π-acidity; less π-acidic ligands give decreased enantioselectivities. The enantioselectivity of allylic amination reactions using I and their derived palladium complexes increases as the cone angle of the phosphine increases. Allylic alkylation of (allyl)(methyl)carbonate with a carborane-containing phenylacetic acid ester gives an (allyl)(carboranyl)phenylacetate ester in up to 73% ee, the first direct asym. reaction for a carborane derivative

European 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 C2H2N4O2, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Ubale, Akash S. published the artcileTransition-Metal-Free Alkylative Aromatization of Tetralones using Alcohols/Amino Alcohols Toward the Synthesis of Bioactive Naphthol and Benzo[e/g]indole Derivatives, Name: 2-Aminobutan-1-ol, the publication is Journal of Organic Chemistry (2022), 87(12), 8104-8117, database is CAplus and MEDLINE.

Herein, the synthesis of bioactive naphthols I (R¹ = H, 6-Br, 6-MeO, 7-MeO; R² = Ph, 3-MeC₆H₄, 2-thienyl, etc.) and II or benzindoles III (R³ = Me, Et, PhCH₂, etc.) and IV by alkylative aromatization of the corresponding 1- and 2-tetralones with alcs. R²CH₂OH or amino alcs. H₂NCHR³CH₂OH in the presence of NaOH using aerobic oxidative cross-coupling protocol is reported. This is a general and transition-metal-free method, which uses an inexpensive base, does not require inert conditions, and furnishes water and hydrogen peroxide as byproducts. Moreover, this method is compatible with a wide substrate scope and showed exclusive regioselectivity.

Journal of Organic 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 C10H15NO, Name: 2-Aminobutan-1-ol.

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

Holmes, J. L. published the artcileHeats of formation of ionic and neutral enols of acetaldehyde and acetone, SDS of cas: 20117-47-9, the publication is Journal of the American Chemical Society (1982), 104(9), 2648-9, database is CAplus.

CH₂:C(OH)R (I, R = H, Me) are formed, together with C₂H₄, in the pyrolysis of II (R = H, Me) at 950°/10^-3 torr in a tubular quartz reactor leading to an ionization chamber; the pyrolysis of II (R = Me) at >950° gave CH₄ and CH₂:CO at the expense of enol. The ionization energies, accurately determined by the impact of a monoenergetic electron beam and the ionization efficiency curve threshold, were 9.15 ± 0.05 and 8.48 ± 0.05 eV. The low cross-section for ionization of I is due to the small Franck-Condon factors for the adiabatic transition which are related to the difference in the preferred conformation of the OH group in I and its radical cation. The formation heat of I and its radical cations are calculated; the enol radical cations are more stable than the keto or aldehyde radical cations in contrast to the neutral species. The formation heat increment for the -OCH: fragment was also estimated

Journal of the American Chemical Society 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

Shiau, Timothy P. published the artcileSulfonyl-polyol N,N-dichloroamines with rapid, broad-spectrum antimicrobial activity, Name: (R)-Oxiran-2-ylmethanol, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(20), 5650-5653, database is CAplus and MEDLINE.

The discovery and development of antimicrobial agents that do not give rise to resistance remains an ongoing challenge. Our efforts in this regard continue to reveal new potential therapeutic agents with differing physicochem. properties while retaining the effective N,N-dichloroamine pharmacophore as the key antimicrobial warhead. In this Letter, disclosed are agents containing polyol units as a water solubilizing group. These sulfonyl-polyol agents show broad spectrum bactericidal and virucidal activity. These compounds show 1h MBC’s of 16-512 μg/mL against Escherichia coli and 4-256 μg/mL against Staphylococcus aureus at neutral pH, and 1-h IC₅₀‘s of 4.5-32 μM against Adenovirus 5 and 0.7-3.0 μM against Herpes simplex virus 1. The lead compounds were tested in a tissue culture irritancy assay and showed only minimal irritation at the highest concentrations tested.

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 C14H18BNO2, Name: (R)-Oxiran-2-ylmethanol.

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

Zhang, Yongjie published the artcilePyrazolo[1,5-a]pyrimidine based Trk inhibitors: Design, synthesis, biological activity evaluation, HPLC of Formula: 96-20-8, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 127712, database is CAplus and MEDLINE.

Tropomyosin receptor kinases (Trks), a transmembrane receptor tyrosine kinases, have attracted more and more attention as antitumor drug targets. Here we reported the structure-based synthesis and biol. evaluation of novel pyrazolo[1,5-a]pyrimidine derivatives, i.e., I, as Trk inhibitors, which exhibited potent Trk inhibitory activities. Particularly, some of the compounds (8a, 8f, 9a, 9b and 9f) (IC₅₀ < 5 nM) showed significant inhibitory potency against Trk.

Bioorganic & Medicinal Chemistry 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 C8H6ClF3, HPLC of Formula: 96-20-8.

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