Category: alcohols-buliding-blocks

Su, Xinluona published the artcileDiffusion of phenolic compounds within high-silica MFI-type zeolite in the mesitylene solution, Category: alcohols-buliding-blocks, the publication is Microporous and Mesoporous Materials (2021), 111044, database is CAplus.

The intracrystalline diffusivity of phenolic compounds (phenol, p-propylphenol and m-cresol) and toluene within silicalite-1 and MFI-type zeolite with Si/Al = 303 (H-MFI) in the liquid phase (solvent: mesitylene) in the temperature range from 313 to 353 K were measured by using the constant volumetric method. The amounts of phenol, p-propylphenol, and toluene adsorbed onto silicalite-1 at 313, 323 and 353 K were approx. the same, whereas less m-cresol was adsorbed because of its larger kinetic diameter Unlike adsorbed toluene, adsorbed of phenol displayed stronger interactions in H-MFI than in silicalite-1, indicating that hydrogen bonding between the OH group of phenol and Bronsted acid sites in H-MFI enhanced the adsorption of phenol. Whereas the intracrystalline diffusivity of phenol, p-propylphenol, and toluene within silicalite-1 are approx. the same, m-cresol exhibited lower intracrystalline diffusivity, indicating that the intracrystalline diffusivity was governed by geometrical limitation. The intracrystalline diffusivity of phenol was lower within H-MFI with acid sites than within silicalite-1. The residence time of phenol on the acid sites became longer than that of toluene, which led to a difference in the intracrystalline diffusivity between phenol and toluene within H-MFI.

Microporous and Mesoporous Materials published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C20H17FO4S, Category: alcohols-buliding-blocks.

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

Munakala, Anandarao published the artcileSteric and Electronic Control Intramolecular [2 + 2]-Cycloaddition of Cyclohexadienone-Containing 1,7-Enynes, Category: alcohols-buliding-blocks, the publication is Organic Letters (2022), 24(3), 892-896, database is CAplus and MEDLINE.

Herein, authors have developed silver-catalyzed an electronic and steric control intramol. formal [2 + 2]-cycloaddition of alkyne-tethered cyclohexadienones. Substrates with electron-rich alkynes and less hindered quaternary carbon center afford tricyclic fused-cyclobutenes through 1,7-enyne cyclization. In contrast, the formation of dihydrofurans was observed from electron-deficient alkynes via proton abstraction/C-O bond cleavage. The synthetic potential of this method was also broadened with a gram-scale reaction and various transformations on cyclobutene.

Organic Letters published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Category: alcohols-buliding-blocks.

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

Mushtaq, Sajid published the artcileEfficient and Site-Specific ¹²⁵I-Radioiodination of Bioactive Molecules Using Oxidative Condensation Reaction, Formula: C8H19NO2, the publication is ACS Omega (2018), 3(6), 6903-6911, database is CAplus and MEDLINE.

In this report, the novel and site-specific radioiodination of biomols. by using aryl diamine and alkyl aldehyde condensation reaction in the presence of a Cu²⁺ catalyst under ambient conditions was reported. ¹²⁵I-labeled alkyl aldehyde was synthesized using a tin precursor with a high radiochem. yield (72 ± 6%, n = 5) and radiochem. purity (>99%). The utility of the radioiodinated precursor was demonstrated through aryl diamine-installed c[RGDfK(C)] peptide and human serum albumin (HSA). Radioiodinated c[RGDfK(C)] peptide and HSA protein were synthesized with high radiochem. yields and purity. ¹²⁵I-HSA protein showed excellent in vivo stability and negligible thyroid uptake as compared with directly radioiodinated HSA by using the tyrosine group. Excellent reaction kinetics and the in vitro and in vivo stabilities of ¹²⁵I-labeled alkyl aldehyde have suggested the usefulness of the strategy for the radioiodination of bioactive mols.

ACS Omega 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, Formula: C8H19NO2.

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

Smolobochkin, Andrey V. published the artcileSynthesis and evaluation of water-soluble 2-aryl-1-sulfonylpyrrolidine derivatives as bacterial biofilm formation inhibitors, SDS of cas: 6346-09-4, the publication is Chemistry & Biodiversity (2019), 16(1), n/a, database is CAplus and MEDLINE.

The approach to the novel 1-[(2-aminoethyl)sulfonyl]-2-arylpyrrolidines via unique intramol. cyclization/aza-Michael reactions of N-(4,4-diethoxybutyl)ethenesulfonamide have been developed, which benefits from high yields of target compounds, mild reaction conditions, usage of inexpensive and low-toxic reagents, and allows for wide variability in both amine and aryl moieties. Biotesting with whole-cell luminescent bacterial biosensors responding to DNA damage showed that all tested compounds are not genotoxic. Tested compounds differently affect the formation of biofilms by Vibrio aquamarinus DSM 26054. Some of the tested compounds were found to suppress the bacterial biofilms growth and thus are promising candidates for further studies.

Chemistry & Biodiversity 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 C10H11NO4, SDS of cas: 6346-09-4.

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

Lunsford, Carl D. published the artcilePreparation of 4-amino-1-butanols and some derivatives of pharmacological interest, Synthetic Route of 4543-95-7, the publication is Journal of Organic Chemistry (1957), 1225-8, database is CAplus.

The 4-alkylamino (I) and 4-dialkylamino-1-butanols (II) were prepared by LiAlH₄ reduction of the product from equimolar amounts of butyrolactone (III) and a primary or secondary amine. Use of 2 moles amine resulted in N,N’-symmetrically substituted putrescines. The 3-aminopropanols were prepared similarly by the substitution of propiolactone (IV) for III. The 3,4,5-trimethoxybenzoates, the diphenylacetates, and the benzhydryl ethers of some of the II and of N-3-hydroxypropylpiperidine (V) and their quaternary salts were prepared and their pharmacol. activity examined III (68.8 g.) and 104 g. NHBu₂ heated 4 hrs. at 150°, the mixture in Et₂O added dropwise to 25.1 g. LiAlH₄ in 300 ml. Et₂O, refluxed 1 hr., the excess hydride decomposed with H₂O, the mixture filtered, the filtrate concentrated, and the residue fractionated gave 97.4 g. II (di-Bu derivative), b₄₀ 172-5°. When the starting amine refluxed below 150°, the reaction with III was carried out at reflux until the pot temperature reached 150° where it was kept 4 hrs.; when the starting amine was NHMe₂ or NHEt₂ the reaction was run in a sealed tube at 150°. The following results were obtained in preparing I and II, RR’N(CH₂)₄OH (RR’N, b.p./mm., % yield, n²⁵_D, and d. given): BuNH, 80-0.5°/0.2, 44, 1.4503, 0.8900; PhCH₂NH, 137-40°/0.8, 56, 1.5288, -; Me₂N, 98°/22, 56, 1.4390, 0.8798; Et₂N, 83-5°/0.8, 80, 1.4460, 0.8653; Pr₂N, 114°/4.3, 77, 1.4472, 0.8723; Bu₂N, 135°/0.3, 62, 1.4502, 0.8616; (CH₂)₅N, 75°/0.2, 71, 1.4733, 0.9471. III (172 g.) and 180 g. NHMe₂ heated 4 hrs. at 200° in 2 sealed tubes, the mixture heated to 125° in vacuo, and reduced with 125 g. LiAlH₄ gave 86 g. N,N,N’,N’-tetramethylputrescine, b₂₈ 78-80°, n²⁵_D 1.4261, d₂₇ 0.7864; dipicrate, m. 203-5°. There was also a higher-boiling fraction which proved to be II (di-Me derivative). Similarly, 17.2 g. III, 34 g. piperidine, and 11.4 g. LiAlH₄ gave 25 g. 1,4-piperidinobutane, b_0.3 117-18°; HCl salt, m. above 300°. IV (28.4 g.) added dropwise to 34 g. piperidine at 5-10° and towards the end of the addition the temperature allowed to rise to 20°, the sirup dissolved in 100 ml. tetrahydrofuran and reduced as above with 11.4 g. LiAlH₄, and the product fractionally distilled gave 31 g. V, b₂₅ 117-22°, n²⁵_D 1.4750, d²⁹₂₅ 0.9585; 3,4,5-trimethoxybenzoate hydrochloride, 51% yield, m. 169-71°; diphenylacetate nitrate, 90% yield, m. 115-16°(H₂O); diphenylacetate-MeI, m. 144.5-46° (alc.); diphenylacetate-MeBr, m. 165-6° (iso-PrOH). The 3,4,5-trimethoxybenzoic acid and diphenylacetic acid esters of I and II were prepared from the acid chloride with I or II. 3,4,5-Trimethoxybenzoyl chloride (23 g.) in 50 ml. CHCl₃ refluxed 2 hrs. with 11.7 g. II (di-Me derivative), the residue partitioned between dilute HCl and Et₂O, the acid extract made alk. and extracted with Et₂O, dried, and separated gave 26 g. II 3,4,5-trimethoxybenzoate-HCl, m. 122-4°. The quaternary salts of both the esters and the ethers were prepared by addition of MeI or MeBr to the base in Et₂O. When crystallization did not occur spontaneously the Et₂O was decanted and the oil crystallized from a suitable solvent. The following RCO₂(CH₂)NR”R’₂X were thus formed (R, R’, R”, X, m.p., and % yield given): 3,4,5-(MeO)₃C₆H₂, Me, H, Cl, 122-4°, 75; 3,4,5-(MeO)₃C₆H₂, Et, H, Cl, 140-1°, 97; 3,4,5-(MeO)₃C₆H₂, Et, Me, I, 142.5-44°, 78; 3,4,5-(MeO)₃C₆H₂, Pr, H, Cl, 118-19°, 35; 3,4,5-(MeO)₃C₆H₂, Pr, Me, I, 115-17°, 37; 3,4,5-(MeO)₃C₆H₂, [R’₂ = (CH₂)₅], H, Cl, 156.5-57°, 83; 3,4,5-(MeO)₃C₆H₂, [R’₂ = = (CH₂)₅], Me, I, 171-3°, 35; Ph₂CH, [R’₂ = (CH₂)₅], H, Cl, 148-50°, 53; Ph₂CH, [R’₂ = (CH₂)₅], Me, I, 69-72°, 34; Ph₂CH, [R’₂ = (CH₂)₅], Me, Br, 144-6°, 61. Benzhydryl bromide (49.3 g.) and 69.2 g. 4-dipropylamino-1-butanol in 200 ml. PhMe refluxed 15 hrs., concentrated in vacuo, partitioned between 5% NaOH and Et₂O, the extract then extracted with 5% HCl, this made alk. with 20% NaOH, and extracted with Et₂O gave 39 g. unchanged II (alkyl = Pr) and 26 g. N-(4-benzhydryloxybutyl)-N,N-dipropylamine, b_1.5 175-7°. The following PhRCHO(CH₂)₄NR’R’ were similarly prepared (R, R’R’N, salt, b.p./mm., or m.p., and % yield given): Ph, Et₂N, -, 202-5°/1.4, 68; Ph, Et₂N, HBr, 109-11.5°, -; Ph, Et₂N, MeBr, 120-1°, 81; Ph, Bu₂N, -, 192-4°/1.5, 38; Ph, (CH₂)₅N, -, 217-20°/2.0, 46; Ph, (CH₂)₅N, HCl, 135.5-37°, -; Ph, (CH₂)₅N, MeI, 126-6.5°, 73; p-ClC₆H₄, Et₂N, citrate, 123-4°, 62.

Journal of Organic Chemistry published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Synthetic Route of 4543-95-7.

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

Kavala, Veerababurao published the artcileSyntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol, COA of Formula: C19H14O2, the publication is Tetrahedron (2008), 64(18), 3960-3965, database is CAplus.

Regioselective C-C bond formation of 9-phenyl-9H-xanthen-9-ol 1 with various enolizable ketones I-X in an acidic (HBr) medium, obtained by the reaction of 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) with ketone is observed Except for ketone, 4-methyl-pentan-2-one VII in all other cases examined the attack to xanthenyl carbocation is from the thermodynamically stable enolizable side of the unsym. ketones. In the case of 3-methyl-butan-2-one VIII the equilibrium is in favor of the more stable enolizable ketone, which has large steric factor, hence no reaction was observed during its addition to alc. 1.

Tetrahedron 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, COA of Formula: C19H14O2.

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

Kavala, Veerababurao published the artcileSelf-Assembled Superstructure of Xanthene Derivatives, Quality Control of 596-38-3, the publication is Journal of Chemical Crystallography (2007), 37(8), 527-535, database is CAplus.

Various multi carbon homologations of 9-phenyl-9H-xanthen-9-ol were obtained through a C-C bond formation by reacting it with various enolizable ketones in the presence of 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). All the ten derivatives along with the starting xanthen-9-ol have been characterized by single crystal X-ray diffraction. They all form self-assembled superstructure in the solid state. The self-assembling patterns in these supramol. architectures were explained based on steric and electronic nature of the pendant arm.

Journal of Chemical Crystallography 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, Quality Control of 596-38-3.

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

Fawcett, Alexander published the artcileStrain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines, Computed Properties of 608534-44-7, the publication is Journal of the American Chemical Society (2019), 141(11), 4573-4578, database is CAplus and MEDLINE.

Azetidines are important motifs in medicinal chem., but there are a limited number of methods for their synthesis. Herein, the authors present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodol. is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodol. was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib.

Journal of the American Chemical Society published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Computed Properties of 608534-44-7.

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

Park, Jaeyong published the artcileTotal chemocatalytic cascade conversion of lignocellulosic biomass into biochemicals, Recommanded Product: 4-Propylphenol, the publication is Applied Catalysis, B: Environmental (2022), 121280, database is CAplus.

Because of its complexity, selective conversion of lignocellulosic biomass into platform chems. presents significant challenges. Herein, we converted birch wood into high-yield lignin-derived phenolic monomers and dimers and holocellulose-derived polyols and monocarboxylic acids via a two-step cascade reaction using 0.1 wt% Pd on N-doped carbon (Pd_0.1/CN_x) and passivated alumina-coated Ni on activated carbon (Ni₂ @Al₂O₃/AC) catalysts. The catalytic fractionation of birch sawdust using Pd_0.1/CN_x produced 11.1 wt% monomers, 5.6% dimers, and 63.4 wt% pulp-rich solid (PRS) based on feed weight The subsequent conversion of PRS over passivated Ni₂ @Al₂O₃/AC produced 21.6 wt% C₂-C₆ polyols and 7.9 wt% monocarboxylic acids. After the whole biomass conversion reaction, the Pd_0.1/CN_x and Ni₂ @Al₂O₃/AC catalysts were separated using their different magnetic responses and reused three times without activity loss. The structure-performance relationships of the Pd_0.1/CN_x catalysts synthesized using different methods and effect of passivation on the performance of the Ni₂ @Al₂O₃/AC catalyst were analyzed.

Applied Catalysis, B: Environmental published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Recommanded Product: 4-Propylphenol.

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