Tag: M.W=100-150

Hunter, Gordon A. published the artcileChemical and spectroscopic properties of the 3-hydroxythiophene [thiophen-3(2H)-one] system, Name: Thiophen-3-ol, the publication is New Journal of Chemistry (2010), 34(11), 2558-2563, database is CAplus.

3-Hydroxythiophene 1 spontaneously dimerizes to 4,5-dihydro-5-(3-hydroxythien-2-yl)thiophen-3(2H)-one 14. 3-Hydroxythiophenes 1E and 4-10E exist in solvent-dependent equilibrium with their thiophen-3(2H)-one 1K and 4-10K tautomers; the amount of hydroxy tautomer is greater than in the case of the corresponding 3-hydroxypyrroles. 3-Hydroxythiophenes are much less reactive to electrophiles than corresponding 3-hydroxypyrroles, but the 5-methylsulfanyl derivative 10 reacts at the 2-position with methoxymethylene Meldrum’s acid and undergoes Vilsmeier formylation. The enolates derived from 3-hydroxythiophenes by treatment with base can be O-alkylated and O-acylated with high regioselectivity. 2,2-Disubstituted thiophen-3(2H)-ones undergo equilibrium conjugate addition with nucleophiles, but the resulting adducts could not be isolated.

New Journal of Chemistry published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Name: Thiophen-3-ol.

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

Hunter, Gordon A. published the artcileSynthesis of 3-hydroxythiophenes and thiophen-3(2H)-ones by pyrolysis of alkylsulfanylmethylene Meldrum’s acid derivatives, Name: Thiophen-3-ol, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1995), 1209-14, database is CAplus.

3-Hydroxythiophene [thiophen-3(2H)-one] and a range of its 2-substituted, 2,2-disubstituted and 5-substituted derivatives have been made by flash vacuum pyrolysis (FVP) of an appropriate alkylsulfanylmethylene derivatives of Meldrum’s acid. These compounds are readily obtained, either by reaction of methoxymethylene Meldrum’s acid with alkylthiols in refluxing acetonitrile, or via the bis(methylsulfanyl) compound I by known procedures. The pyrolysis proceeds by a hydrogen-transfer-cyclization mechanism in which there is extensive loss of configuration of a chiral center at the reaction site. The NMR and mass spectra of the Meldrum’s acid precursors and the mass spectra of the 3-hydroxythiophenes [thiophen-3(2H)-ones] are briefly discussed.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Name: Thiophen-3-ol.

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

Hunter, Gordon A. published the artcileSimple 3-hydroxythiophenes [thiophen-3(2H)-ones], Category: alcohols-buliding-blocks, the publication is Journal of the Chemical Society, Chemical Communications (1990), 375-6, database is CAplus.

A simple and flexible synthetic route to simple 3-hydroxythiophenes [thiophen-3(2H)-ones], including the parent compound I, was reported. Thus, pyrolysis of Meldrum’s and derivative II at 625° gave 92% hydroxythiophene III.

Journal of the Chemical Society, Chemical Communications published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Category: alcohols-buliding-blocks.

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

Kyasa, ShivaKumar published the artcileSynthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals, Safety of Triethylsilanol, the publication is Journal of Organic Chemistry (2015), 80(24), 12100-12114, database is CAplus and MEDLINE.

Although transfer of electrophilic alkoxyl (“RO+”) from organic peroxides to organometallics offers a complement to traditional methods for etherification, application has been limited by constraints associated with peroxide reactivity and stability. We now demonstrate that readily prepared tetrahydropyranyl monoperoxyacetals react with sp³ and sp² organolithium and organomagnesium reagents to furnish moderate to high yields of ethers. The method is successfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed O,O-acetals, and S,S,O-orthoesters. In contrast to reactions of dialkyl and alkyl/silyl peroxides, the displacements of monoperoxyacetals provide no evidence for alkoxy radical intermediates. At the same time, the high yields observed for transfer of primary, secondary, or tertiary alkoxides, the latter involving attack on neopentyl oxygen, are inconsistent with an S_N2 mechanism. Theor. studies suggest a mechanism involving Lewis acid promoted insertion of organometallics into the O-O bond.

Journal of Organic Chemistry published new progress about 597-52-4. 597-52-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is Triethylsilanol, and the molecular formula is C6H16OSi, Safety of Triethylsilanol.

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

Serusi, Lorenzo published the artcileThe First Highly Enantioselective Synthesis of 3-Sulfinyl-Substituted Isoindolinones Having Adjacent Carbon and Sulfur Stereocenters, Application In Synthesis of 4410-99-5, the publication is Journal of Organic Chemistry (2021), 86(15), 10630-10639, database is CAplus and MEDLINE.

A highly stereoselective access to 3-sulfinyl-substituted isoindolinones was achieved by a tandem organocatalytic addition/cyclization reaction of 2-carbobenzyloxy-N-tosylbenzylidenimine with thiols and succeeding diastereoselective oxidation with MCPBA. First, enantioenriched isoindolinone N,S-acetals was obtained through a dynamic kinetic asym. transformation induced by a bifunctional chiral thiourea organocatalyst. In turn, the newly created carbon stereocenter enabled a high diastereocontrol in the subsequent sulfoxidation Based on DFT calculations, a theor. rationale for the stereoselectivity of the oxidation reaction was also provided.

Journal of Organic Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C13H13N, Application In Synthesis of 4410-99-5.

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

Priebbenow, Daniel L. published the artcileDiscovery of Potent and Fast-Acting Antimalarial Bis-1,2,4-triazines, Safety of 3,3,3-Trifluoropropan-1-ol, the publication is Journal of Medicinal Chemistry (2021), 64(7), 4150-4162, database is CAplus and MEDLINE.

Novel 3,3′-disubstituted-5,5′-bi(1,2,4-triazine) compounds with potent in vitro activity against Plasmodium falciparum parasites were recently discovered. To improve the pharmacokinetic properties of the triazine derivatives, a new structure-activity relationship (SAR) investigation was initiated with a focus on enhancing the metabolic stability of lead compounds These efforts led to the identification of second-generation highly potent antimalarial bis-triazines, exemplified by triazine 23(I), which exhibited significantly improved in vitro metabolic stability (8 and 42μL/min/mg protein in human and mouse liver microsomes). The disubstituted triazine dimer 23 was also observed to suppress parasitemia in the Peters 4-day test with a mean ED₅₀ value of 1.85 mg/kg/day and exhibited a fast-killing profile, revealing a new class of orally available antimalarial compounds of considerable interest.

Journal of Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Safety of 3,3,3-Trifluoropropan-1-ol.

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

Pramanik, Milan published the artcilet-BuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols, SDS of cas: 4410-99-5, the publication is Organic & Biomolecular Chemistry (2022), 20(13), 2671-2680, database is CAplus and MEDLINE.

Selective addition of aliphatic thiols or alcs. R¹XH (X = O, R¹ = Me, Et, F₃CCH₂, n-decyl, etc.; X = S, R¹ = i-Bu, PhCH₂, n-dodecyl, 2-furylmethyl, etc.) to N-aryl propiolamides HCCC(O)NHR² (R² = Ph, 2-MeC₆H₄, 3,4-Cl₂C₆H₃, etc.) using lithium tert-butoxide in ethanol as a promoter is described. Mechanistically, it was shown that the reaction proceeds through the generation of a thiyl radical intermediate, and the amide group in N-phenylpropiolamide helps in the activation of the alkyne, which led to thioacetalization via the formation of a (Z)-selective anti-Markovnikov vinyl sulfide. The (Z)-selectivity during the formation of vinyl sulfides was controlled by an intramol. sulfur···oxygen interaction.

Organic & Biomolecular Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, SDS of cas: 4410-99-5.

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

Pramanik, Milan published the artcileSulfur···oxygen interaction-controlled (Z)-selective anti-Markovnikov vinyl sulfides, Category: alcohols-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(46), 5698-5701, database is CAplus and MEDLINE.

The sulfur oxygen (S···O) interaction was used herein to obtain (Z)-selective anti-Markovnikov vinyl sulfides from the addition of thiyl radicals to N-aryl propynamides. DFT calculations predicted that S···O interaction originated from the delocalization of the lone-pair of the carbonyl oxygen to the adjacent σ^* orbital of the S atom of C-S.

Chemical Communications (Cambridge, United Kingdom) published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Category: alcohols-buliding-blocks.

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

Mizukado, Junji published the artcileInsertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to OH bond, Application In Synthesis of 2240-88-2, the publication is Journal of Fluorine Chemistry (2005), 126(3), 365-369, database is CAplus.

ROCHF₂-type fluorinated ethers were synthesized by the reaction of hexafluoropropene oxide (HFPO) with alc. or phenol. In this reaction, although the insertion reaction of difluorocarbene to O-H bond and the nucleophilic attack of alc. or phenol to HFPO were competition, the insertion reaction proceeded predominantly to give fluorinated ether in the case of low nucleophilic alc. or phenol. In addition, high reaction pressure is advantageous to the selectivity of the fluorinated ethers in the reaction of HFPO with (CF₃)₂CHOH or C₆F₅OH.

Journal of Fluorine Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Application In Synthesis of 2240-88-2.

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

Mizukado, Junji published the artcileReactions of aliphatic fluoro-alcohols with CHClF₂ at atmospheric pressure, HPLC of Formula: 2240-88-2, the publication is Journal of Fluorine Chemistry (2006), 127(3), 400-404, database is CAplus.

The reactions of aliphatic fluoro-alcs. with chlorodifluoromethane (CHClF₂) at atm. pressure were examined In the reaction of CF₃CF₂CH₂OH, the difluoromethylated ether was obtained in moderate yield by using ethers such as 1,4-dioxane, diglyme, and THF, or their mixtures with water as a reaction solvent. While acetal and orthoformate were also produced, the selectivity of the difluoromethylated ether could be improved by adding water to the reaction. The effect of water could be explained by the reaction mechanism.

Journal of Fluorine Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, HPLC of Formula: 2240-88-2.

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