Category: alcohols-buliding-blocks

Qudrat-i-Khuda, M. published the artcileInvestigations on Ocimum gratissimum. II. Characterization of gratissimin and gratissimic acid, Related Products of alcohols-buliding-blocks, the publication is Sci. Res. (Dacca, Pakistan) (1965), 2(1/2), 8-10, database is CAplus.

cf. CA 62, 81191g. Reduction of gratissimum C₂₀H₂O₄ (I) with Li-AlH₄ has given a diol, C₁₈H₂₀O₂, m.p. 104 °, which forms ditoluene-p-sulfonyl derivative, m.p. 184°, confirms the mol. formula and evidence the presence of 2 COOCH₃ groups in the mol. Acetic anhydride converts gratissimic acid (II) into a crystalline anhydride, m.p. 187°. Oxidation of II with KMnO₄ has afforded a high yield of benzoic acid. Results indicate that I is dimethyl ester of α-truxillic acid (III) and II is identical with this acid, which has been confirmed by comparing these compounds with III and its dimethyl ester prepared from trans-cinnamic acid.

Sci. Res. (Dacca, Pakistan) published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Related Products of alcohols-buliding-blocks.

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

Troutman, Jerry M. published the artcileTuning the Production of Variable Length, Fluorescent Polyisoprenoids Using Surfactant-Controlled Enzymatic Synthesis, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biochemistry (2015), 54(18), 2817-2827, database is CAplus and MEDLINE.

Bactoprenyl diphosphate (BPP), a two-E eight-Z configuration C₅₅ isoprenoid, serves as a critical anchor for the biosynthesis of complex glycans central to bacterial survival and pathogenesis. BPP is formed by the polymerase undecaprenyl pyrophosphate synthase (UppS), which catalyzes the elongation of a single farnesyl diphosphate (FPP) with eight Z-configuration isoprene units from eight isopentenyl diphosphates. In vitro anal. of UppS and other polyprenyl diphosphate synthases requires the addition of a surfactant such as Triton X-100 to stimulate the release of the hydrophobic product from the enzyme for effective and efficient turnover. Here using a fluorescent 2-nitrileanilinogeranyl diphosphate analog of FPP, we have found that a wide range of surfactants can stimulate release of product from UppS and that the structure of the surfactant has a major impact on the lengths of products produced by the protein. Of particular importance, shorter chain surfactants promote the release of isoprenoids with four to six Z-configuration isoprene additions, while larger chain surfactants promote the formation of natural isoprenoid lengths (8Z) and larger. We have found that the product chain lengths can be readily controlled and coarsely tuned by adjusting surfactant identity, concentration, and reaction time. We have also found that binary mixtures of just two surfactants can be used to fine-tune isoprenoid lengths. The surfactant effects discovered do not appear to be significantly altered with an alternative isoprenoid substrate. However, the surfactant effects do appear to be dependent on differences in UppS between bacterial species. This work provides new insights into surfactant effects in enzymol. and highlights how these effects can be leveraged for the chemoenzymic synthesis of otherwise difficult to obtain glycan biosynthesis probes. This work also provides key reagents for the systematic anal. of structure-activity relationships between glycan biosynthesis enzymes and isoprenoid structure.

Biochemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C15H20O6, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

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

Omran, Anahid published the artcileSynthesis of 3-(3-hydroxyphenyl)pyrrolidine dopamine D₃ receptor ligands with extended functionality for probing the secondary binding pocket, Category: alcohols-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(10), 1897-1902, database is CAplus and MEDLINE.

A series of 3-(3-hydroxyphenyl)pyrrolidine analogs which incorporate N-alkyl groups and N-butylamide-linked benzamide functionality were synthesized and their in vitro binding affinities at human dopamine receptors were evaluated. The authors’ ligand design strategy was to take the 3-(3-hydroxyphenyl)pyrrolidine scaffold and extend functionality from the orthosteric binding site to the secondary binding pocket for enhancing affinity and selectivity for the D₃ receptor. The N-alkyl analogs constitute a homologous series from N-pentyl to N-decyl to probe the length/bulk tolerance of the secondary binding pocket of the D₃ receptor. Enantiomeric 3-(3-hydroxyphenyl)pyrrolidine analogs were also prepared to test the chirality preference of the orthosteric binding site for this scaffold. Benzamide analogs were prepared to enhance affinity and/or selectivity based upon the results of the homologous series.

Bioorganic & Medicinal Chemistry Letters published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Category: alcohols-buliding-blocks.

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

Dindarloo Inaloo, Iman published the artcileNickel-Catalyzed Synthesis of N-(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride, Application of Thiophen-3-ol, the publication is ChemCatChem (2020), 12(21), 5486-5491, database is CAplus.

A simple and efficient domino reaction has been designed and employed for the one-pot synthesis of N-(hetero)aryl carbamates ArNHC(O)OR (Ar = Ph, thiophen-2-yl, pyridin-3-yl, etc.; R = Pr, cyclohexyl, allyl, etc.) through the reaction between alcs. ROH and in-situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C-O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6-trichloro-1,3,5-triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N-(hetero)aryl carbamates in good yields with high functional groups compatibility.

ChemCatChem 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, Application of Thiophen-3-ol.

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

Arriaga Alba, M. published the artcileMutagenicity of urine from mice exposed orally to nitrite and various aminated antiparasitic drugs, Application of N-Benzyl-N,N-dimethyl-2-phenoxyethanaminium 3-hydroxy-2-naphthoate, the publication is Environmental and Molecular Mutagenesis (1989), 14(1), 13-19, database is CAplus and MEDLINE.

The mutagenic activity of mouse urine was determined after oral administration of sodium nutrite and pyrantel pamoate, chloroquine, piperazine, dehydroemetine, iodochlorhydroxyquin, and bephenium hydroxynaphthoate. The simultaneous administration of piperazine or chloroquine with sodium nitrite produced urinary mutagens that appeared conjugated as glucuronides, whereas pyrantel pamoate and dehydroemetine in the presence of nitrite caused only slight mutagenic urine. No mutagenic activity was detected in the urine of mice to which halogenated derivatives of tertiary amines (iodochlorhydroxyquin) or quaternary ammonium salts (bephenium hydroxynaphthoate) were administered together with nitrite.

Environmental and Molecular Mutagenesis published new progress about 3818-50-6. 3818-50-6 belongs to alcohols-buliding-blocks, auxiliary class Anti-infection,Antiparasitic, name is N-Benzyl-N,N-dimethyl-2-phenoxyethanaminium 3-hydroxy-2-naphthoate, and the molecular formula is C28H29NO4, Application of N-Benzyl-N,N-dimethyl-2-phenoxyethanaminium 3-hydroxy-2-naphthoate.

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

Arriaga Alba, M. published the artcileMutagenicity of products generated by the reaction between several antiparasitic drugs and nitrite, HPLC of Formula: 3818-50-6, the publication is Environmental and Molecular Mutagenesis (1988), 12(1), 65-73, database is CAplus and MEDLINE.

Drugs containing secondary aliphatic amines, heterocyclic N, or secondary aliphatic amido groups (chloroquine, dihydroemetine, mebendazole, and piperazine) and pyrimidine derivatives such as pyrantel pamoate were reacted in vitro with NaNO₂ at pH 3.7 and became mutagenic for Salmonella typhimurium strain TA1535. The products derived from the nitrosation of chloroquine and dehydroemetine required metabolic activation by mammalian hepatic S9 to be mutagenic. The N-nitroso derivatives of mebendazole, piperazine, and pyrantel pamoate were mutagenic with and without S9, although more activity was noted in the presence of S9 with the nitrosated compounds formed from mebendazole and piperazine. Under identical conditions, no mutagenic products were detected from quaternary ammonium salts such as bephenium hydroxynaphthoate or drugs containing tertiary heterocyclic amino groups, such as iodochlorhydroxyquin.

Environmental and Molecular Mutagenesis published new progress about 3818-50-6. 3818-50-6 belongs to alcohols-buliding-blocks, auxiliary class Anti-infection,Antiparasitic, name is N-Benzyl-N,N-dimethyl-2-phenoxyethanaminium 3-hydroxy-2-naphthoate, and the molecular formula is C28H29NO4, HPLC of Formula: 3818-50-6.

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

Cortinas de Nava, C. published the artcileMutagenicity of antiamebic and anthelmintic drugs in the Salmonella typhimurium microsomal test system, Product Details of C28H29NO4, the publication is Mutation Research, Genetic Toxicology Testing (1983), 117(1-2), 79-91, database is CAplus and MEDLINE.

Amebicides (chloroquine (I) [54-05-7], diiodohydroxyquin  [83-73-8], iodochlorohydroxyquin  [130-26-7] and dehydroemetine  [4914-30-1]) and anthelmintics (bephenium hydroxynaphthoate  [3818-50-6], 4-hexylresorcinol  [136-77-6], mebendazole  [31431-39-7], niclosamide  [50-65-7], pyrantel pamoate  [22204-24-6] and pyrvinium pamoate  [3546-41-6]) were tested for mutagenicity in the S. typhimurium microsomal test system. Frameshift mutations were induced by dehydroemetine and niclosamide following activation by microsomal enzymes, while pyrvinium pamoate induced both frameshift and base-pair substitution mutations with or without metabolic activation. The urine of mice treated with dehydroemetine or pyrvinium pamoate showed no mutagenic activity. However, urine obtained from mice treated with niclosamide was mutagenic in strains TA98 and TA1538. The fluctuation assay showed I to be mutagenic in TA1537, a strain which detects frameshift mutations.

Mutation Research, Genetic Toxicology Testing published new progress about 3818-50-6. 3818-50-6 belongs to alcohols-buliding-blocks, auxiliary class Anti-infection,Antiparasitic, name is N-Benzyl-N,N-dimethyl-2-phenoxyethanaminium 3-hydroxy-2-naphthoate, and the molecular formula is C28H29NO4, Product Details of C28H29NO4.

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

Bolano, Tamara published the artcileAn Acyl-NHC Osmium Cooperative System: Coordination of Small Molecules and Heterolytic B-H and O-H Bond Activation, Name: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, the publication is Organometallics (2015), 34(15), 3902-3908, database is CAplus.

The hexahydride complex OsH₆(PⁱPr₃)₂ (1) activates the C-OMe bond of 1-(2-methoxy-2-oxoethyl)-3-methylimidazolium chloride (2), in addition to promoting the direct metalation of the imidazolium group, to afford a five-coordinate OsCl(acyl-NHC)(PⁱPr₃)₂ (3) compound The latter coordinates carbon monoxide, oxygen, and mol. hydrogen to give the corresponding carbonyl (4), dioxygen (5), and dihydrogen (6) derivatives Complex 3 also promotes the heterolytic bond activation of pinacolborane (HBpin), using the acyl oxygen atom as a pendant Lewis base. The hydride ligand and the Bpin substituent of the Fischer-type carbene of the resulting complex 7 activate the O-H bond of alcs. and water. As a consequence, complex 3 is a metal ligand cooperating catalyst for the generation of mol. hydrogen, by both the alcoholysis and hydrolysis of pinacolborane, via the intermediates 7 and 6.

Organometallics published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Name: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol.

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

Luk’yanov, S. M. published the artcileConversion of 1,3-benzodioxans into xanthene derivatives, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol, the publication is Zhurnal Organicheskoi Khimii (1978), 14(2), 399-401, database is CAplus.

Treatment of dioxanes I (R = Ph, Me) with Ph₃C⁺ClO^–₄ in HOAc gave 21-62.8% II, which was also prepared by reaction of o-HOC₆H₄CPh₂OH with Ph₃C⁺ClO₄^– or HClO₄. Treatment of II with BrCH₂CO₂Et and Zn gave 93% III (R¹ = CH₂CO₂Et) III (R¹ = p-H₂NC₆H₄, p-Me₂NC₆H₄, EtO) were also prepared

Zhurnal Organicheskoi Khimii published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol.

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

Pospisil, Jan published the artcileOxidation of catechol. IV. Oxidation of 4-tert-octylcatechol, HPLC of Formula: 1139-46-4, the publication is Chemicke Listy pro Vedu a Prumysl (1958), 939-47, database is CAplus.

cf. C.A. 52, 4546g. Oxidation of 4-tert-octylcatechol (I) (tert-octyl = R = Me₃CCH₂CMe₂) with O or alk. H₂O₂ gave 2-hydroxy-5-tert-octyl-1,4-benzoquinone (II), also obtained by oxidation of 4-tert-octyl-1,2-benzoquinone (III). The oxidation of I is assumed to proceed through intermediate 1,2,4-trihydroxy-5-tert-octylbenzene (IV) to II. A similar mechanism is proposed for the oxidation of catechol (V) to 2,5-dihydroxy-1,4-benzoquinone (VI). Alkylation of pyrogallol (VII) with di-isobutylene (VIII) gave 5-tert-octylpyrogallol (IX) whose oxidation with Ag₂O yielded 6-hydroxy-4-tert-octyl-1,2-benzoquinone (X). Dissolving 110 g. resublimed V in 448 g. hot VIII, treating the solution with 0.2 ml. concentrated H₂SO₄, stirring the mixture 2.5 hrs. at 105-15°, cooling, filtering off the product with suction, and washing with H₂O yielded 167.6 g. I, m. 108° (ligroine). Adding a solution of 4.5 g. I in 220 ml. Et₂O to a mixture of 100 ml. Et₂O, 5 g. anhydrous Na₂SO₄, and Ag₂O prepared from 135 g. AgNO₃, shaking 5 min., filtering, and evaporating gave 4.29 g. III, m. 121-1.5° (Et₂O). Acetylation of 2.2 g. I by heating with 6 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 20 min. on the steam-bath gave 1.8 g. 1,2-diacetoxy-4-tert-octylbenzene, m. 49.5°. The same compound was also obtained by boiling for 10 min. a mixture of 0.44 g. III, 1 g. anhydrous NaOAc, 1.0 g. Zn dust, and 12 ml. Ac₂O. To oxidize I, O was passed into a solution of 68 g. KOH in 300 ml. 75% MeOH at a rate of 0.2-0.3 l./min. at 30°. After 15 min., 10 g. I in 100 ml. 75% MeOH was added over a period of 2.5 hrs. The initial blue color turned red. The red clear solution was diluted with 300 ml. H₂O, 300 g. ice was added, and the mixture acidified with concentrated HCl. The solution turned yellow and a yellow product precipitated Evaporation of the MeOH in vacuo yielded another crop of II, m. 133.5-4.5° (decomposition) (petr. ether) (7.45 g., 70.1% total). Dissolving 4.5 g. I in 50 ml. 5% solution of KOH in 50% MeOH, treating this solution at 40° with 7 ml. 40% H₂O₂ for 30 min., stirring the mixture 1.5 hrs., decanting the red solution from resinous material, diluting it to a 10-fold volume with ice and H₂O, and acidifying with HCl gave 69.8% II. The same compound was obtained also by oxidation of 0.22 g. III in methanolic solution of KOH (containing 4.5 g. KOH in 45 ml. 75% MeOH) by passing 0.15-0.2 l./min. O through the solution 1.5 hrs. (yield 41.3%) or by treating 0.5 g. III in 2.2 ml. MeOH with 2.5 ml. 40% aqueous KOH and 1.4 ml. 40% H₂O₂ 1 hr. at 40° (yield 15.3%, 0.08 g.). Absorption of II in 0.1N aqueous KOH showed log ε 4.086 at 285 mμ, and log ε 3.216 at 495 mμ. Heating 1 g. II with 5 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 2 hrs. at 45° and diluting the mixture after 20 hrs. with 20 ml. H₂O yielded 0.95 g. 2-acetoxy-5-tert-octyl-1,4-benzoquinone (XI), m. 89.5-90° (petr. ether). Dissolving 0.2 g. XI in 5 ml. Ac₂O, adding 0.5 g. Zn dust and 0.5 g. anhydrous NaOAc, refluxing the mixture 30 min., filtering off the Zn, and diluting the filtrate with 25 ml. H₂O and 25 g. ice gave 0.22 g. triacetate (XII) of IV, m. 88.5° (petr. ether). The same compound was obtained by treating similarly 2 g. II in 25 ml. Ac₂O with 2.5 g. Zn dust and 2.5 g. NaOAc; yield 2.62 g. Hydrogenation of 0.11 g. II in 20 ml. glacial AcOH and 40 ml. Ac₂O over PtO₂ and heating the mixture with 0.2 ml. concentrated H₂SO₄ 20 min. under H gave XII. If the hydrogenation was carried out in MeOH, the colorless solution of IV formed was reoxidized in contact with air. Heating 30 g. VII with 172 g. VIII and 0.1 ml. concentrated H₂SO₄ 3 hrs. at 105-15° gave 30.7 g. (51.7%) IX, m. 104° (ligroine). Shaking 1.2 g. IX in 100 ml. Et₂O with 12 g. Ag₂O and 10 g. anhydrous Na₂SO₄ in 50 ml. Et₂O for 10 min. gave a red solution of X whose reductive acetylation by heating with 5 ml. Ac₂O, 0.5 g. NaOAc, and 0.5 g. Zn dust in 30 ml. C₆H₆ gave 1,2,3-triacetoxy-5-tert-octylbenzene, m. 71° (petr. ether). The same compound was also obtained by allowing 0.37 g. III to stand 24 hrs. at 20° with 10 ml. Ac₂O and 0.1 ml. H₂SO₄ or by heating 1 g. IX with 8 ml. Ac₂O and 0.1 ml. H₂SO₄ 10 min. on the steam bath (yield 1.25 g.). Heating 0.28 g. VI, 6 ml. Ac₂O, and 0.1 ml. H₂SO₄ 2 hrs. at 50° and diluting the mixture after 20 hrs. with ice and H₂O gave 0.27 g. 2,5-diacetoxy-1,4-benzoquinone (XIII), m. 151-2° (decomposition) (AcOH). Hydrogenation of 0.14 g. VI in 40 ml. MeOH over PtO₂ at 18° gave impure 1,2,4,5-tetrahydroxybenzene whose acetylation with 5 ml. Ac₂O and 1 drop H₂SO₄ gave tetraacetate, m. 226° (AcOH).

Chemicke Listy pro Vedu a Prumysl published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, HPLC of Formula: 1139-46-4.

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