Tag: 100-200

1,5-Migration of rhodium via C-H bond activation in catalytic decyanative silylation of nitriles was written by Tobisu, Mamoru;Hasegawa, Junya;Kita, Yusuke;Kinuta, Hirotaka;Chatani, Naoto. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2012.Quality Control of (3,4,5-Trifluorophenyl)methanol This article mentions the following:

Unprecedented aryl-to-aryl 1,5-rhodium migration is involved in decyanative silylation of aryl cyanides bearing a tethered arene. The 1,5-migration proceeds through remote C-H bond activation. 1,5-Migration also occurs in other rhodium-catalyzed reactions, including borylation and oxidative Mizoroki-Heck reactions. In the experiment, the researchers used many compounds, for example, (3,4,5-Trifluorophenyl)methanol (cas: 220227-37-2Quality Control of (3,4,5-Trifluorophenyl)methanol).

(3,4,5-Trifluorophenyl)methanol (cas: 220227-37-2) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Quality Control of (3,4,5-Trifluorophenyl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Bioconversion of acetophenones by marine fungi isolated from marine algae Bostrychia radicans and Sargassum sp. was written by Mouad, Ana Maria;Martins, Mariana Provedel;Romminger, Stelamar;Seleghim, Mirna Helena Regali;Leandrini de Oliveira, Ana Ligia;Debonsi, Hosana Maria;Yokoya, Nair Sumie;Fujii, Mutue Toyota;Passarini, Michel Rodrigo Zambrano;Bonugli-Santos, Rafaella Costa;Sette, Lara Duraes;Porto, Andre Luiz Meleiro. And the article was included in Current Topics in Biotechnology in 2012.HPLC of Formula: 171032-87-4 This article mentions the following:

The bioconversion of acetophenone derivatives 1-6 was investigated using whole cells of marine fungi Botryosphaeria sp. Br-09, Eutypella sp. Br-023, Hydropisphaera sp. Br-27 and Xylaria sp. Br-61 isolated from the red alga Bostrychia radicans and Arthopyrenia sp. SGPY-41, Penicillium sp. SMA2-8, Pestalotiopsis sp. SMA2-C isolated from brown alga Sargassum sp. Asym. reduction produced the enantiopure (R)- or (S)-alcs. 7-12 with high enantiomeric excess (>99 % ee). This study describes the first investigation with marine-derived fungi recovered from algae for biocatalytic reduction The fungus Botryosphaeria sp. Br-09 showed excellent reductions for ortho-acetophenone derivatives 1-6. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4HPLC of Formula: 171032-87-4).

(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.HPLC of Formula: 171032-87-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Methane recovery from marine gas hydrates: A bench scale study in presence of low dosage benign additives was written by Bhattacharjee, Gaurav;Choudhary, Nilesh;Barmecha, Vivek;Kushwaha, Omkar S.;Pande, Nawal K.;Chugh, Parivesh;Roy, Sudip;Kumar, Rajnish. And the article was included in Applied Energy in 2019.Quality Control of rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate This article mentions the following:

De-pressurization is one approach which has been found to be economically feasible for methane recovery from marine hydrates. Hydrate dissociation being an endothermic process suggests that de-pressurization alone would not be sufficient and some addnl. stimulation would be required for sustained production from one such reservoir. Thermal stimulation may overcome the challenge posed by the endothermic dissociation process; however, economically it may not be ideal. A possible way out is to use thermal stimulation, but at relatively low temperatures as compared to conventional practice. This would be economical and can be accomplished in the presence of small doses of additives mixed in with the water stream used for thermal stimulation. In the present study, a number of benign additives were identified which when used in low concentrations enhance the kinetics of methane hydrate dissociation compared to pure water. Additives were first shortlisted from a wide potential pool using quantum mech. calculations These additives were later tested for their efficacy in stirred tank reactor to quickly identify the best additives for the job and few selected additives were then studied in a larger bench scale setup (fixed bed configuration) where they were injected in the form of an additive-water stream to dissociate already formed hydrates. Factors such as toxicity of the additive, fluidity of additive-water stream, foam formation on mixing of additive with water, etc. were also taken into account. An energy and efficiency anal. revealed that reported additives enhance the energy ratio and thermal efficiency of the process as compared to pure water stimulation. In the experiment, the researchers used many compounds, for example, rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6Quality Control of rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate).

rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6) 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. 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.Quality Control of rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Derivatives of 1,2,3,4-tetrahydroxybenzene. III. The synthesis of dill apiole and the extension of the Dakin reaction was written by Baker, Wilson;Jukes, E. H. T.;Subrahmanyam, C. A.. And the article was included in Journal of the Chemical Society in 1934.Formula: C7H6O3 This article mentions the following:

1,2,3,4-(HO)₂C₆H₂(OMe)₂ (I) is obtained in 5 g. yield by oxidizing 9.8 g. gallacetophenone 3,4-di-Me ether in 10% NaOH with 75 cc. 3% H₂O₂. I and allyl bromide in Me₂CO-K₂CO₃ give an allyl ether, rearranged on heating to the 5-allyl derivative of I, b₁₄ 160-73° (impure), which reacted with CH₂I₂ in Me₂CO-K₂CO₃ to give dill apiole (1,2-methylenedioxy-3,4-dimethoxy – 5 – allylbenzene), b₁₆ 172-3°. 1,2,3,4-Tetramethoxy-5-allylbenzene, b₁₂ 145°, m. 26°. 1,2,3-C₆H₃(OH)₃, (CH₂Br₂ and K₂CO₃, refluxed for 30 hrs., give pyrogallol methylene ether, m. 65°. 7-Methoxy-8-acetyl-2-methylchromone, m. 161-2°, in quant. yield from the 7-HO derivative; this could not be hydrolyzed to the mono-Me ether or 2,4-diacetylresorcinol. 2,4-(HO)₂C₆H₃COCH₂Ph is oxidized by 3% H₂O₂ in N NaOH in an inert atm., giving 95% of PhCH₂CO₂H and 1,2,4-C₆H₃(OMe)₃; 2,4-(HO)₂C₆H₃COCH₂C₆H₄OMe-p (ononetin) gives 60% of p-MeOC₆H₄CH₂CO₂H; homopiperonylresacetophenone gives 90% of β-piperonylpropionic acid; 2,4-HO(MeO)C₆H₃COCH₂Ph gives 50% of PhCH₂CO₂H. Thus the Dakin reaction appears to be general. In the experiment, the researchers used many compounds, for example, Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2Formula: C7H6O3).

Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Formula: C7H6O3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Biotransformation of Citrus sinensis peel oil and commercial limonene by various fungi and Musa paradisiaca stem enzyme extract was written by Singh, Gurdip;Kapoor, I. P. S.;Kaur, Jaspreet;Singh, O. P.;Vernwal, S. K.;Yadav, R. S. S.;Rao, G. P.;Sharma, S. R.;Leclercq, P. A.;Klinkby, Naja. And the article was included in Journal of Medicinal and Aromatic Plant Sciences in 2002.SDS of cas: 2451-01-6 This article mentions the following:

The essential oil extracted from peel of Citrus sinensis and com. limonene were subjected to biotransformation by various fungi such as Epicocum nigrum, Colletotrichum falcatum, Fusarium moniliforme, F. oxysporum, Trichothecium roseum, Curvularia pallescens and an enzyme extract from Musa paradisiaca stem and their chem. composition has been investigated by HPLC and GC-MS anal. Most of the hydrocarbons of C. sinensis oil were found to be partially oxidized/hydroxylated to alcs. by E. nigrum, Musa paradisiaca enzyme acts as ligases/peroxidases and oxidizes terpene hydrocarbons to oxygenated monoterpenes and higher carboxylic acids and an unknown component I. The chem. composition of com. limonene (E-merck) and biotransformed limonene has also been investigated by HPLC and GC-MS techniques. In the experiment, the researchers used many compounds, for example, rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6SDS of cas: 2451-01-6).

rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 2451-01-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

One-pot synthesis of chiral alcohols from alkynes by CF₃SO₃H/ruthenium tandem catalysis was written by Liu, Huan;Liu, Sensheng;Zhou, Haifeng;Liu, Qixing;Wang, Chunqin. And the article was included in RSC Advances in 2018.Computed Properties of C8H9FO This article mentions the following:

A practical one-pot synthesis of chiral alcs. from readily available alkynes via tandem catalysis by the combination of CF₃SO₃H and a fluorinated chiral diamine Ru(II) complex in aqueous CF₃CH₂OH was described. Very interestingly, the combination of fluorinated catalysts and solvent exhibited a pos. fluorine effect on the reactivity and enantioselectivity. A range of chiral alcs. with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Computed Properties of C8H9FO).

(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) 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.Computed Properties of C8H9FO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Transition-metal-catalyst-free synthesis of anthranilic acid derivatives by transfer hydrogenative coupling of 2-nitroaryl methanols with alcohols/amines was written by Zhang, Shudi;Tan, Zhenda;Xiong, Biao;Jiang, Huan Feng;Zhang, Min. And the article was included in Organic & Biomolecular Chemistry in 2018.Formula: C8H9NO3 This article mentions the following:

A series of anthranilic acid derivatives I [R¹ = H, 6-Me, 4,5-(OMe)₂, etc.; R² = NH₂, i-OPr, NH(CH₂)₂Ph, etc.] was synthesized by transfer hydrogenative coupling of 2-nitroaryl methanols with alcs./amines. The synthesis proceeded with the merits of no need for a transition metal catalyst, operational simplicity, broad substrate scope, good functional tolerance and high step efficiency, which offers a useful alternative to access anthranilic acid derivatives I and II. In the experiment, the researchers used many compounds, for example, (3-Methyl-2-nitrophenyl)methanol (cas: 80866-76-8Formula: C8H9NO3).

(3-Methyl-2-nitrophenyl)methanol (cas: 80866-76-8) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Formula: C8H9NO3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Modulating the Asymmetry of the Active Layer in Pursuit of Nanofiltration Selectivity via Differentiating Interfacial Reactions of Piperazine was written by Gao, Yawei;Zhao, Yangying;Wang, Xiao-mao;Tang, Chuyang;Huang, Xia. And the article was included in Environmental Science & Technology in 2022.Category: alcohols-buliding-blocks This article mentions the following:

Nanofiltration (NF), highly prospective for drinking water treatment, faces a challenge in simultaneously removing emerging contaminants while maintaining mineral salts, particularly divalent cations. To overcome this challenge, NF membranes possessing small pores concomitant with highly neg. charged surfaces were synthesized via a two-step fabrication strategy. The key is to generate a polyamide active layer having a loose and carboxyl group-abundant segment on top and a dense barrier segment underneath. This was achieved by restrained interfacial polymerization between trimesoyl chloride and partly protonated piperazine to form a highly depth-heterogeneous polyamide network, followed by second amidation in an organic environment to remove untethered polyamide fragments and associate malonyl chlorides with reserved amine groups to introduce more neg. charges. Most importantly, on first-principle engineering the spatial architecture of the polyamide layer, amplifying asym. charge distribution was paired with the thinning of the vertical structure. The optimized membrane exhibits high salt/organic rejection selectivity and water permeance superior to most NF membranes reported previously. The rejections of eight emerging contaminants were in the range of 66.0-94.4%, much higher than the MgCl₂ rejection of 41.1%. This new fabrication strategy, suitable for various diacyl chlorides, along with the new membranes so produced, offers a novel option for NF in potable water systems. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Category: alcohols-buliding-blocks).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) 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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Identification and functional characterization of a γ-terpinene synthase in Nigella sativa L (black cumin) was written by Elyasi, Rizan;Majdi, Mohammad;Krause, Sandra T.;Kucukay, Nagihan;Azizi, Abdolbaset;Degenhardt, Jorg. And the article was included in Phytochemistry (Elsevier) in 2022.Electric Literature of C10H14O This article mentions the following:

Nigella sativa (Black cumin) has many applications in food and pharmaceutical industries. Thymoquinone has been considered as a main effective compound in N. sativa seeds and attracted researchers’ attention mainly due to its medicinal potential. In this study, the essential oil components of leaves, flowers and seed developmental stages including half black seeds, soft black seeds and hard black seeds were analyzed in N. sativa. Whereas no terpenes were detected in flowers and leaves, seeds showed an essential oil composition that increased in its thymoquinone content during seed maturation. To study the proposed first step of thymoquinone biosynthesis, the formation of γ-terpinene from geranyl diphosphate (GDP), we identified and functionally characterized a γ-terpinene synthase (NsTPS1) in N. sativa. This monoterpene synthase was identified in RNA sequence data derived from seeds. After heterologous expression in Escherichia coli, partially purified NsTPS1 converted GDP to γ-terpinene. NsTPS1 is the first functionally characterized terpene synthase from N. sativa and displays a higher similarity to other terpene synthases from Ranunculaceae than known γ-terpinene synthases from more distant plant species. Characterization of NsTPS1 elucidates the first dedicated step in the biosynthesis of thymoquinone in N. sativa and paves the way towards metabolic engineering for high-level thymoquinone production A full-length N. sativa monoterpene synthase (NsTPS1) was identified and deposited in Genbank with the accession number OM856342. In the experiment, the researchers used many compounds, for example, 5-Isopropyl-2-methylphenol (cas: 499-75-2Electric Literature of C10H14O).

5-Isopropyl-2-methylphenol (cas: 499-75-2) 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.Electric Literature of C10H14O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The Friedel-Crafts reaction. VI. Further evidence for γ-substitution in resorcinol and orcinol derivatives was written by Desal, R. D.;Vakil, V. M.. And the article was included in Proceedings – Indian Academy of Sciences, Section A in 1940.Formula: C9H10O3 This article mentions the following:

AcCl (20 cc.) was added gradually to a solution of 12 g. anhydrous orcinol and 26 g. anhydrous AlCl₃ in 150 cc. PhNO₂ and the mixture allowed to stand for 24 h., then heated on the water bath for 2 h., yielding 8 g. γ-orcacetophenone (I), needles, m. 142-4°; oxime, needles, m. 211-12°; p-nitrophenylhydrazone, red microcrystalline plates, m. 245° (in 3 out of 7 experiments a mixture of β-and γ-orcacetophenones was formed instead of only the γ-variety; these were separated by crystallization from C₆H₆). Clemmensen reduction of I yielded 2-ethyl-5-methylresorcinol, needles, m. 135°. A mixture of 14 g. anhydrous AlCl₃, 12 g. orcinol and 17 g. BzCl in 75 cc. PhNO₂, after standing overnight, was heated on the water bath for 1 h., yielding after trituration with NaHCO₃ solution and crystallization of the residue from C₆H₆, pale yellow needles of 2,4-dihydroxy-5-methylbenzophenone, m. 138°. Treatment of either β- or γ-orcacetophenone in PhNO₂ solution with Ac₂O in the presence of anhydrous AlCl₃ gave lustrous needles of 2,4-diacetyl-5-methylresorcinol, m. 95°, giving a purple-red color with FeCl₃; p-nitrophenylhydrazone, red microcrystalline needles, m. 242°. A mixture of 20 g. resacetophenone, 24 g. BzCl and 18 g. of AlCl₃ in 200 cc. PhNO₂ was heated on the water bath for 2 h.; after treatment of the product with NaHCO₃, solution in 5% NaOH, acidification of the solution and exhaustive extraction of the dry solid with petr. ether, the residue was crystallized from C₆H₆ and from alc., yielding 0.8 g. of pale yellow lustrous needles of 2-benzoyl-4-acetylresorcinol (II), m. 165°, gives a red color with FeCl₃ solution; p-nitrophenylhydrazone, red microcrystalline powder, m. above 300°; the petr. ether solution yielded lustrous plates (from alc.) of 4-O-benzoyl-resacetophenone (III), m. 110° mono-Br derivative, lustrous needles from alc., m. 176°. II could not be brominated at room temperature either in CHCl₃ or glacial AcOH; it could not be condensed with Ac₂O in presence of anhydrous AlCl₃. III (2 g.) heated with 4 g. anhydrous AlCl₃ at 140° for 1.5 h. underwent the Fries transformation to give II. BzCl (1.7 g.) was gradually added to 2 g. Me 2,4-dihydroxy-5-acetylbenzoate and 1.6 g. anhydrous AlCl₃ in 50 cc. PhNO₂ and the mixture heated for 6 h. at 130-40° and allowed to stand overnight, yielding 42% of Me 2,4-dihydroxy-3-benzoyl-5-acetylbenzoate (IV), needles, m. 204°; its alc. solution gives a red color with FeCl₃. Saponification of IV with KOH gave the acid (V), needles, m. 217°, whose alc. solution gave a red color with FeCl₃. V heated at 220-25° for 1 h. gave pale yellow needles (from alc.) of 2-benzoyl-4-acetylresorcinol, m. 165°. A mixture of 10 g. anhydrous AlCl₃, 7 g. 4-benzoylresorcinol, 4 g. Ac₂O and 75 cc. PhNO₂ was heated 6 h. on the water bath; the product after solution in 5% NaOH solution and precipitation with acid was exhaustively extracted with petr. ether, yielding, (1) upon concentration of the petr. ether solution, 30% of 2-acetyl-4-benzoyl-resorcinol, needles, m. 107-8°, whose alc. solution gave a wine-red color with FeCl₃ (p-nitrophenylhydrazone, red microcrystalline powder, m. 227-9°), and (2) after crystallization of the residue from dilute alc., 5% of 2,6-diacetyl-4-benzoyl-resorcinol, m. 151°, whose alc. solution gave a cherry-red color with FeCl₃ (p-nitrophenylhydrazone, reddish microcrystalline powder, m. 288-90° (decomposition)). 2-Acetylresorcinol (1 g.), 1 g. AlCl₃ and 1.2 g. BzCl in 30 cc. PhNO₂ after standing at ordinary temperature was heated 1 h. on the water bath. After treatment with NaHCO₃ solution, the residue was extracted with petr. ether; the petr. ether solution upon concentration gave 2-acetyl-4-benzoylresorcinol (VI), needles, m. 108°. Friedel-Crafts condensation of VI with Ac₂O yielded 2,6-diacetyl-4-benzoylresorcinol, m. 151°. In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0Formula: C9H10O3).

2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Formula: C9H10O3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts