Tag: M.W=50-100

Ding, Shi published the artcileExploration of the structure-activity relationship and druggability of novel oxazolidinone-based compounds as Gram-negative antibacterial agents, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Archiv der Pharmazie (Weinheim, Germany) (2019), 352(11), 1900129, database is CAplus and MEDLINE.

To gain further knowledge of the structure-activity relationship and druggability of novel oxazolidinone-based UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) inhibitors as Gram-neg. antibacterial agents, compounds containing the hydrophobic tails with different lengths and terminal substitutions were synthesized and their antibacterial activities against standard and clin. isolated Gram-neg. strains were evaluated. We summarized their structure-activity relationships and found that oxazolidinone-based compounds exhibited a narrower antibacterial spectrum compared with threonine-based compounds Furthermore, we parallelly compared the metabolic stabilities of the compounds with the classic threonine scaffold and the novel oxazolidinone scaffold in liver microsomes. The results indicated that the druggability of the oxazolidinone scaffold may be inferior to the classic threonine scaffold in the design of LpxC inhibitors.

Archiv der Pharmazie (Weinheim, Germany) 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, Recommanded Product: (R)-Oxiran-2-ylmethanol.

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

White, James D. published the artcileStudies of the Synthesis of Providencin: Construction and Assembly of Two Major Subunits, Application of (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2014), 79(2), 700-710, database is CAplus and MEDLINE.

The “northern” sector of the cembranoid diterpene providencin (I) containing a tetrasubstituted cyclobutane was synthesized from the bis(acetonide) of D-glucose using dicyclopentadienylzirconium(0)-mediated oxygen abstraction from a furanose. Oxidative scission of the vinyl substituent of this cyclobutane gave an aldehyde, which was reacted with an alkynylstannane to provide an allenol (II). Cyclization of the derived allenone with silver nitrate led to a cyclobutylfuran (III) comprising the northern subunit of providencin. The “southern” sector of the cembranoid skeleton containing a trisubstituted iodoalkene attached to an α-phenylselenyl-γ-lactone was synthesized from (R)-glycidol. Negishi carbometalation-iodination established the (E)-iodoalkene, and addition of the lithio dianion of phenylselenoacetic acid to a tosylate generated the substituted lactone (IV). The two sectors were joined via stannylation of the furan of the northern component followed by Stille cross-coupling of the furylstannane with the iodoalkene of the southern subunit. Linkage of the two segments was also made at C12-C13 of providencin using intermol. aldol condensation of the enolate from the selenyl lactone of the southern portion with an acetaldehyde appendage on the cyclobutane of the northern sector. Closure of the providencin macrocycle from these conjoined subunits was unsuccessful.

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 C15H15OP, Application of (R)-Oxiran-2-ylmethanol.

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

Bhunia, Susmita published the artcileCatalytic olefin epoxidation over cobalt(II)-containing mesoporous silica by molecular oxygen in dimethylformamide medium, Application In Synthesis of 57044-25-4, the publication is Catalysis Science & Technology (2014), 4(6), 1820-1828, database is CAplus.

A cobalt(II) Schiff base complex has been immobilized onto the surface of Si-MCM-41 to prepare a new catalyst. The amine group-containing organic moiety 3-aminopropyl-triethoxysilane had first been anchored on the surface of Si-MCM-41 via a silicon alkoxide route. Upon condensation with salicylaldehyde, the amine group affords a bidentate Schiff-base moiety in the mesoporous matrix, which is subsequently used for anchoring of cobalt(II) centers. The prepared catalyst has been characterized by UV-vis, IR, EPR spectroscopic and small angle X-ray diffraction (XRD) analyses, and N₂ sorption studies. The catalytic activity was tested in epoxidation reactions of olefinic compounds, including styrene and allyl alc., with mol. oxygen at atm. pressure in DMF medium in the absence of addnl. sacrificial reductant. The reactions seemed to proceed through a radical formation mechanism. The immobilized catalyst showed good activity and epoxide selectivity in the alkene epoxidation Notably, the catalyst can be recovered and reused without any loss of activity.

Catalysis Science & Technology 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, Application In Synthesis of 57044-25-4.

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

Davies, Jacob published the artcileNi-Catalyzed carboxylation of aziridines en route to β-amino acids, Product Details of C4H11NO, the publication is Journal of the American Chemical Society (2021), 143(13), 4949-4954, database is CAplus and MEDLINE.

A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO₂ at atm. pressure is disclosed. The protocol is characterized by its mild conditions, exptl. ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.

Journal of the American Chemical Society 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, Product Details of C4H11NO.

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

Ko, Young Ok published the artcileRh(II)/Mg(O^tBu)₂-Catalyzed Tandem One-Pot Synthesis of 1,4-Oxazepines and 1,4-Oxazines from N-Sulfonyl-1,2,3-triazoles and Glycidols, Related Products of alcohols-buliding-blocks, the publication is Organic Letters (2016), 18(24), 6432-6435, database is CAplus and MEDLINE.

A novel, one-pot route for the synthesis of nonaromatic ring-fused 1,4-oxazepines and 1,4-oxazines has been developed. The reaction features a sequential rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with glycidols, followed by a regioselective Lewis acid Mg(O^tBu)₂-catalyzed intramol. ring-opening reaction. It has been found that the regioselectivity in the epoxide ring-opening was largely determined by the substituents on the glycidols. Thus, substituted glycidols I (R² ≠ H) afforded seven-membered oxazepine derivatives selectively, e.g. II, while unsubstituted glycidols I (R² = H) afforded six-membered oxazine derivatives, e.g. III. Plausible reaction pathways are elucidated and supported by experiments with several glycidols bearing different substituents around the epoxide functionality.

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, Related Products of alcohols-buliding-blocks.

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

Tolmacheva, Irina A. published the artcileSynthesis and evaluation of antiviral activities of triterpenic conjugates with 2-aminobutan-1-ol as potent microbicidal agents, Recommanded Product: 2-Aminobutan-1-ol, the publication is Medicinal Chemistry Research (2019), 28(10), 1648-1660, database is CAplus.

The effect of the synthetic modifications of the triterpenic A ring on the level of antiviral activity of triterpenic C3, C28 amides with a residue of racemic, (S), or (R)-enantiomeric 2-aminobutan-1-ol against herpes simplex viruses type I (HSV-I) and type II (HSV-II), as well as against human immunodeficiency virus type I (HIV-1) was investigated. The 2,3-secolupane racemic amide 5a was selected as a potent microbicidal agent with the highest virus inhibitory (against HSV-I and HSV-II) and virucidal (against HSV-1 and HIV-1) actions, the antiviral activity of which was provided by the (S)-enantiomeric conjugate 5b.

Medicinal Chemistry Research 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 C19H21N3O, Recommanded Product: 2-Aminobutan-1-ol.

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

Deng, Danfeng published the artcileNNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation, Formula: C4H11NO, the publication is Organometallics (2018), 37(14), 2386-2394, database is CAplus.

The bidentate 6-picolinoyl 2,2′-bipyridine (bpy) ruthenium complex (6-HOC₅H₃NCO-bpy)Ru(CO)₂Cl₂ (2) transforms to a tridentate product I (3, L¹ = L² = Cl; n = 0), which further reacted with MeONa in the presence of PPh₃ to convert to two complexes, (4, 5; shown as I, 4, L¹ = L² = PPh₃, n = 1; 5, L¹ = Cl, L² = PPh₃, n = 0), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcs. with amino alcs. were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

Organometallics 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

Moe, Luke A. published the artcileRemarkable Aliphatic Hydroxylation by the Diiron Enzyme Toluene 4-Monooxygenase in Reactions with Radical or Cation Diagnostic Probes Norcarane, 1,1-Dimethylcyclopropane, and 1,1-Diethylcyclopropane, Application of 1-Methylcyclobutan-1-ol, the publication is Biochemistry (2004), 43(50), 15688-15701, database is CAplus and MEDLINE.

Toluene 4-monooxygenase (T4MO) catalyzes the hydroxylation of toluene to yield 96% p-cresol. This diiron enzyme complex was used to oxidize norcarane (bicyclo[4.1.0]heptane), 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane, substrate analogs that can undergo diagnostic reactions upon the production of transient radical or cationic intermediates. Norcarane closely matches the shape and volume of the natural substrate toluene. Reaction of isoforms of the hydroxylase component of T4MO (T4moH) with different regiospecificities for toluene hydroxylation (k_cat ≈ 1.9-2.3 s^-1 and coupling efficiency ≈ 81-96%) revealed similar catalytic parameters for norcarane oxidation (k_cat ≈ 0.3-0.5 s^-1 and coupling efficiency ≈ 72%). The products included variable amounts of the un-rearranged isomeric norcaranols and cyclohex-2-enyl methanol, a product attributed to rearrangement of a radical oxidation intermediate. A ring-expansion product derived from the norcaranyl C-2 cation, cyclohept-3-enol, was not produced by either the natural enzyme or any of the T4moH isoforms tested. Comparative studies of 1,1-dimethylcyclopropane and 1,1-diethylcyclopropane, diagnostic substrates with differences in size and with ∼50-fold slower k_cat values, gave products consistent with both radical rearrangement and cation ring expansion. Examination of the isotopic enrichment of the incorporated O-atoms for all products revealed high-fidelity incorporation of an O-atom from O₂ in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products was predominantly obtained by reaction with H₂O. The results show a divergence of radical and cation pathways for T4moH-mediated hydroxylation that can be dissected by diagnostic substrate probe rearrangements and by changes in the source of oxygen used for substrate oxygenation.

Biochemistry 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, Application of 1-Methylcyclobutan-1-ol.

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

Ruzicka, Frank published the artcileMethane monooxygenase catalyzed oxygenation of 1,1-dimethylcyclopropane. Evidence for radical and carbocationic intermediates, COA of Formula: C5H10O, the publication is Biochemistry (1990), 29(7), 1696-700, database is CAplus and MEDLINE.

Methane monooxygenase of Methylosinus trichosporium catalyzes the oxygenation of 1,1-dimethylcyclopropane in the presence of O₂ and NADH to (1-methylcyclopropyl)methanol(81%), 3-methyl-3-buten-1-ol (6%), and 1-methylbutanol (13%). Oxygenation by ¹⁸O₂ using the purified enzyme proceeds with incorporation of ¹⁸O into the products. Inasmuch as methane monooxygenase catalyzes the insertion of O from O₂ into a C-H bond of alkanes, (1-methylcyclopropyl)methanol appears to be a conventional oxygenation product. 3-Methyl-3-buten-1-ol is a rearrangement product that can be rationalized on the basis that enzymic oxygenation of 1,1-dimethylcyclopropane proceeds via the (1-methylcyclopropyl)carbinyl radical, which is expected to undergo rearrangement with ring opening to the homoallylic 3-methyl-3-buten-1-yl radical in competition with conventional with ring opening to the homoallylic 3-methyl-3-butenyl-1-yl radical in competition with conventional oxygenation. Oxygenation of the latter radical gives 3-methyl-3-buten-1-ol. 1-Methylcyclobutanol is a ring-expansion product, whose formation is best explained on the basis that the 1-methylcyclobutyl tertiary carbocation is an oxygenation intermediate. This cation would result from rearrangements of carbocations derived by 1-electron oxidation of either radical intermediate. The fact that both 3-methyl-3-buten-1-ol and 1-methylcyclobutanol are produced suggests that the oxygenation mechanism involves both radical and carbocationic intermediates. Radicals and carbocations can both be intermediates if they are connected by an electron-transfer step. A reasonable reaction sequence is one in which the cofactor (μ-oxo)diiron reacts with O₂ and 2-electrons to generate a H atom-abstracting species and an oxidizing agent. The H-abstracting species might be the enzymic radical or another species generated by the Fe complex and O₂. Oxygenation then could proceed by abstraction for a H atom from the substrate to form a radical, followed by electron transfer from the radical to the oxidizing species to form a carbocation. The carbocation would be quenched by O associated with the oxygenation cofactor to generate the product.

Biochemistry 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

Burgers, Peter C. published the artcileMetastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Product Details of C5H10O, the publication is Organic Mass Spectrometry (1982), 17(3), 123-6, database is CAplus.

A simple, accurate, and reproducible method for measuring the appearance energy of a metastable peak is reported. The method involves comparison of the metastable-peak intensity with that of a standard metastable peak, over a small range of ionizing electron energies above their onsets. Six fragmentation processes whose reaction energetics are well established, e.g., AcOMe→ MeC⁺O + OMe•, provided suitable metastable peaks for calibration. Results for fragmentations having large kinetic shifts, e.g., PhBr → [Ph]⁺ + Br•, and for primary and secondary ion decompositions are reported.

Organic Mass Spectrometry 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, Product Details of C5H10O.

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