Category: alcohols-buliding-blocks

Pyran derivatives. 107. Preparation and reactions of 2-acetyl-3-amino-5-hydroxy-2-cyclohexenones; benzene derivatives from pyrones was written by Eiden, Fritz;Patzelt, Gertrud. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1985.Quality Control of 2′,6′-Dihydroxy-4′-methylacetophenone This article mentions the following:

Acetylpyrene I reacted with HNR₂² [NR₂² = NMe₂, NEt₂, NMeCH₂CH₂Ph, piperidino, morpholino, perhydroazepine, 4-(2-pyridyl)-1-piperazinyl, 4-methyl-1-piperazinyl, 4-[3-(trifluoromethyl)phenyl]-1-piperazinyl, 1-piperazinyl] gave aminocyclohexenones II and III and aminophenols IV. NH₃ and 1,2-C₆H₄(NH₂)₂ gave pyridinones V (R = H, 2-H₂NC₆H₄) or VI. The amine group in II (R² = Me) (VII) was replaced by reaction with NH₃, amines, amino acids, and hydrazine derivatives VII cyclized with PhC(:NH)NH₂ or H₂NNHR¹ (R¹ = Ph, Me) to give quinazoline VIII or indazoles IX. Treating II, III, the transamination analogs of VII, VIII, or IX with KOH in EtOH gave the corresponding phenol dehydration products. In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0Quality Control of 2′,6′-Dihydroxy-4′-methylacetophenone).

2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of 2′,6′-Dihydroxy-4′-methylacetophenone

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cobalt-catalyzed alkoxycarbonylation of ethers: Direct synthesis of α-oxy esters from phenols and alcohols was written by Wang, Le-Cheng;Xu, Jian-Xing;Wu, Xiao-Feng. And the article was included in Journal of Catalysis in 2022.COA of Formula: C7H7ClO This article mentions the following:

A cobalt-catalyzed direct alkoxycarbonylation of ethers (such as THF, 1,4-dioxane, ethoxyethane, etc.) has been accomplished. This new catalytic system allows the use of ethers, important building blocks in organic synthesis, as the carbonylation substrates. A variety of phenols and alcs. ROH was transformed to the corresponding α-oxy ester derivatives ROC(O)R¹ (R¹ = oxolan-2-yl, 1,4-dioxan-2-yl, 1-ethoxyethyl, etc.; R = Ph, naphthalen-2-yl, pyridin-3-yl, adamantan-1-yl, etc.) in high yields with excellent functional group tolerance. In addition, several pharmaceutical and bioactive mol. related compounds were also suitable substrates for this carbonylation process, and the target products were obtained in good yields. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7COA of Formula: C7H7ClO).

(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.COA of Formula: C7H7ClO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Stereoisomeric Tris-BINOL-Menthol Bulky Monophosphites: Synthesis, Characterisation and Application in Rhodium-Catalysed Hydroformylation was written by Felgueiras, Alexandre P.;Rodrigues, Fabio M. S.;Carrilho, Rui M. B.;Cruz, Pedro F.;Rodrigues, Vitor H.;Kegl, Tamas;Kollar, Laszlo;Pereira, Mariette M.. And the article was included in Molecules in 2022.Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

Four stereoisomeric monoether derivatives, based on axially chiral (R)- or (S)-BINOL bearing a chiral (+)- or (-)-neomenthyloxy group were synthesized and fully characterised by NMR spectroscopy and X-ray crystallog. The resp. tris-monophosphites were thereof prepared and fully characterised. The coordination ability of the new bulky phosphites with Rh(CO)₂(acac), was attested by ³¹P NMR, which presented a doublet in the range of δ = 120 ppm, with a 1J(103Rh-31P) coupling constant of 290 Hz. The new tris-binaphthyl phosphite ligands were further characterised by DFT computational methods, which allowed to calculate an electronic (CEP) parameter of 2083.2 cm-1 and an extremely large cone angle of 345°, decreasing to 265° upon coordination with a metal atom. Furthermore, the monophosphites were applied as ligands in rhodium-catalyzed hydroformylation of styrene, leading to complete conversions in 4 h, 100% chemoselectivity for aldehydes and up to 98% iso-regioselectivity. The Rh(I)/phosphite catalytic system was also highly active and selective in the hydroformylation of disubstituted olefins, including (E)-prop-1-en-1-ylbenzene and prop-1-en-2-ylbenzene. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Retrospective analysis in 46 women with vulvovaginal atrophy treated with ospemifene for 12 weeks: improvement in overactive bladder symptoms was written by Schiavi, Michele Carlo;Zullo, Marzio Angelo;Faiano, Pierangelo;D’Oria, Ottavia;Prata, Giovanni;Colagiovanni, Vanessa;Giannini, Andrea;Di Tucci, Chiara;Perniola, Giorgia;Di Donato, Violante;Monti, Marco;Muzii, Ludovico;Benedetti Panici, Pierluigi. And the article was included in Gynecological Endocrinology in 2017.HPLC of Formula: 128607-22-7 This article mentions the following:

Aims: The aim of this study was to assess the effectiveness and safety of ospemifene in the improvement of overactive bladder (OAB) symptoms in postmenopausal women affected by vulvovaginal atrophy (VVA). Methods: Forty-six postmenopausal patients affected by VVA with OAB syndrome were enrolled for the study. All patients received Ospemifene 60 mg for 12 wk. Clin. examination, 3-day voiding diary, urodynamic testing, ultrasound measurement of endometrial and bladder wall thickness (BWT) and the Vaginal Health Index (VHI) were performed at baseline and 12 wk. Patients completed the OAB-Q SF and UDI-6. Results: After 12-wk, the number of patients with detrusor overactivity decreased from 39% to 13% (p = 0.04). The reduction in the mean number in 24 h of voids (9.57 ± 2.12 vs. 6.63 ± 1.22, p < 0.0001), urgent micturition episodes/24 h (5.63 ± 1.46 vs. 1.44 ± 1.31, p < 0.0001), nocturia episodes (3.17 ± 0.85 vs. 1.11 ± 1.18, p < 0.0001), urinary incontinence episodes/24 h (0.85 ± 0.96 vs. 0.33 ± 0.64, p = 0.003) was observed The UDI-6, OAB-Q symptoms, OAB-Q (HRQL) scores were 8.95 ± 0.91 vs. 5.56 ± 1.40, 62.60 ± 14.70 vs. 20.08 ± 10.83 and 18.71 ± 7.41 vs. 79.45 ± 14.47 (p < 0.001) before and after 12 wk. Conclusion: Ospemifene is an effective potential therapy for postmenopausal women with VVA improving OAB symptoms and quality of life. In the experiment, the researchers used many compounds, for example, (Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7HPLC of Formula: 128607-22-7).

(Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.HPLC of Formula: 128607-22-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes was written by Dogan, Ozdemir;Isci, Muhammet;Aygun, Muhittin. And the article was included in Tetrahedron: Asymmetry in 2013.Safety of (R)-2-Aminobutan-1-ol This article mentions the following:

A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray anal. In the experiment, the researchers used many compounds, for example, (R)-2-Aminobutan-1-ol (cas: 5856-63-3Safety of (R)-2-Aminobutan-1-ol).

(R)-2-Aminobutan-1-ol (cas: 5856-63-3) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Safety of (R)-2-Aminobutan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Evaluation of Fe and Ru Pincer-Type Complexes as Catalysts for the Racemization of Secondary Benzylic Alcohols was written by Bornschein, Christoph;Gustafson, Karl P. J.;Verho, Oscar;Beller, Matthias;Baeckvall, Jan-E.. And the article was included in Chemistry – A European Journal in 2016.Recommanded Product: 120121-01-9 This article mentions the following:

Fe and Ru pincer-type catalysts are used for the racemization of benzylic alcs. Racemization with the Fe catalyst was achieved within 30 min. under mild reaction conditions, with a catalyst loading as low as 2 mol %. This reaction constitutes the first example of an iron-catalyzed racemization of an alc. The efficiency for racemization of the Fe catalyst and its Ru analog was evaluated for a wide range of sec-benzylic alcs. The com. available Ru complex proved to be highly robust and even tolerated the presence of water in the reaction mixture In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Recommanded Product: 120121-01-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Inhibition of human sulfotransferase 2A1-catalyzed sulfonation of lithocholic acid, glycolithocholic acid, and taurolithocholic acid by selective estrogen receptor modulators and various analogs and metabolites was written by Bansal, Sumit;Lau, Aik Jiang. And the article was included in Journal of Pharmacology and Experimental Therapeutics in 2019.Reference of 128607-22-7 This article mentions the following:

The present study was done to characterize the sulfonation of LCA, GLCA, and TLCA and to investigate whether triphenylethylene (clomifene, tamoxifen, toremifene, ospemifene, droloxifene), benzothiophene (raloxifene, arzoxifene), tetrahydronaphthalene (lasofoxifene, nafoxidine), indole (bazedoxifene), and benzopyran (acolbifene) classes of selective estrogen receptor modulator (SERM) inhibit LCA, GLCA, and TLCA sulfonation. Human recombinant SULT2A1, but not SULT2B1b or SULT1E1, catalyzed LCA, GLCA, and TLCA sulfonation, whereas each of these enzymes catalyzed DHEA sulfonation. LCA, GLCA, and TLCA sulfonation is catalyzed by human liver cytosol, and SULT2A1 followed the substrate inhibition model with comparable apparent Km values (=1 muM). The potency and extent of inhibition of LCA sulfonation were attenuated or increased by structural modifications to toremifene, bazedoxifene, and lasofoxifene. The inhibitory effect of raloxifene, bazedoxifene, and acolbifene on LCA sulfonation was also observed in HepG2 human hepatocellular carcinoma cells. Overall, among the SERMs investigated, bazedoxifene and raloxifene were the most effective inhibitors of LCA, GLCA, and TLCA sulfonation. These findings provide insight into the structural features of specific SERMs that contribute to their inhibition of SULT2A1-catalyzed LCA sulfonation. Inhibition of LCA, GLCA, and TLCA detoxification by a SERM may provide a biochem. basis for adverse effects associated with a SERM. In the experiment, the researchers used many compounds, for example, (Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7Reference of 128607-22-7).

(Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 128607-22-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Photolabile ROMP gels using ortho-nitrobenzyl functionalized crosslinkers was written by Hu, Xiaoran;Shi, Junfeng;Thomas, Samuel W. III. And the article was included in Polymer Chemistry in 2015.Application of 60463-12-9 This article mentions the following:

This paper describes a series of four ortho-nitrobenzyl substituted bis(norbornene) crosslinkers that are suitable for the preparation of photoresponsive organogels and hydrogels through ring-opening metathesis polymerization As measured by several techniques-visual inspections, rheol., and release of network-bound polymers-organogels prepared using these four crosslinkers varied in their sensitivity to UV irradiation by about two orders of magnitude. The reactivity of the gels shows qual. correlation with the stability of the intermediate benzylic radicals. Gels with larger crosslink densities required longer UV irradiation time to dissolve than gels with smaller crosslink densities. Together, these results demonstrate how rational changes to the structures of crosslinkers and gels can tune photosensitivity. Finally, we show a proof-of-concept photochem. release experiment of a phys. entrapped fluorescent polymer from a photolabile ROMP hydrogel. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Application of 60463-12-9).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application of 60463-12-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Induction of the Prenylated Stilbenoids Arachidin-1 and Arachidin-3 and Their Semi-Preparative Separation and Purification from Hairy Root Cultures of Peanut (Arachis hypogaea L.) was written by Sharma, Amit Raj;Gajurel, Gaurav;Ahmed, Izzeldin;Roedel, Krystian;Medina-Bolivar, Fabricio. And the article was included in Molecules in 2022.Recommanded Product: (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol This article mentions the following:

Prenylated stilbenoids such as arachidin-1 and arachidin-3 are stilbene derivatives that exhibit multiple pharmacol. activities. We report an elicitation strategy using different combinations of cyclodextrin, hydrogen peroxide, Me jasmonate and magnesium chloride to increase arachidin-1 and arachidin-3 production in peanut hairy root cultures. The treatment of hairy root cultures with cyclodextrin with hydrogen peroxide selectively enhanced arachidin-1 yield (132.6 ± 20.4 mg/L), which was 1.8-fold higher than arachidin-3. Similarly, cyclodextrin combined with Me jasmonate selectively enhanced arachidin-3 yield (178.2 ± 6.8 mg/L), which was 5.5-fold higher than arachidin-1. Re-elicitation of the hairy root cultures further increased the levels of arachidin-1 and arachidin-3 by 24% and 42%, resp. The Et acetate extract of the culture medium was consecutively fractionated by normal- and reversed-phase column chromatog., followed by semi-preparative HPLC purification on a C18 column to yield arachidin-1 with a recovery rate of 32% and arachidin-3 with a recovery rate of 39%, both at higher than 95% purity. This study provided a sustainable strategy to produce high-purity arachidin-1 and arachidin-3 using hairy root cultures of peanuts combined with column chromatog. and semi-preparative HPLC. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6Recommanded Product: (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Recommanded Product: (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures was written by Li, Shenhuan;Li, Jie;Xia, Tianlai;Zhao, Wanxiang. And the article was included in Chinese Journal of Chemistry in 2019.Formula: C9H9F3O This article mentions the following:

The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl acetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5Formula: C9H9F3O).

2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Formula: C9H9F3O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts