Tag: 100-200

Reduction of acetophenone derivatives by Spirulina platensis and Nostoc minutum was written by Utsukihara, Takamitsu;Koshimura, Masahiro;Abe, Chika;Matsumiya, Takuya;Horiuchi, C. Akira. And the article was included in BioChemistry: An Indian Journal in 2014.Category: alcohols-buliding-blocks This article mentions the following:

The reduction of acetophenone derivatives using Spirulina platensis and Nostoc minutum was investigated. It was found that acetophenone derivatives were reduced with good enantioselectivity. The reduction followed Prelog’s rule, giving the (S)-alcs. in all cases. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Category: alcohols-buliding-blocks).

(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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Engineering an alcohol dehydrogenase with enhanced activity and stereoselectivity toward diaryl ketones: reduction of steric hindrance and change of the stereocontrol element was written by Wu, Kai;Yang, Zhijun;Meng, Xiangguo;Chen, Rong;Huang, Jiankun;Shao, Lei. And the article was included in Catalysis Science & Technology in 2020.SDS of cas: 120121-01-9 This article mentions the following:

Steric hindrance in the binding pocket of an alc. dehydrogenase (ADH) has a great impact on its activity and stereoselectivity simultaneously. Due to the subtle structural difference between two bulky Ph substituents, the asym. synthesis of diaryl alcs. by bioreduction of diaryl ketones is often hindered by the low activity and stereoselectivity of ADHs. To engineer an ADH with practical properties and to investigate the mol. mechanism behind the asym. biocatalysis of diaryl ketones, we engineered an ADH from Lactobacillus kefiri (LkADH) to asym. catalyze the reduction of 4-chlorodiphenylketones (CPPK), which are not catalyzed by the wild type (WT) enzyme. Mutants seq1-seq5 with gradually increased activity and stereoselectivity were obtained through iterative “shrinking mutagenesis.” The final mutant seq5 (Y190P/I144V/L199V/E145C/M206F) demonstrated the highest activity and excellent stereoselectivity of >99% ee. Mol. simulation analyses revealed that mutations may enhance the activity by eliminating steric hindrance, inducing a more open binding loop and constructing more noncovalent interactions. The pro-R pose of CPPK with a halogen bond formed a pre-reaction conformation more easily than the pro-S pose, resulting in the high ee of (R)-CPPO in seq5. Moreover, different halogen bonds formed due to the different positions of chlorine substituents, resulting in opposite substrate binding orientation and stereoselectivity. Therefore, the stereoselectivity of seq5 was inverted toward ortho- rather than para-chlorine substituted ketones. These results indicate that the stereocontrol element of LkADH was changed to recognize diaryl ketones after steric hindrance was eliminated. This study provides novel insights into the role of steric hindrance and noncovalent bonds in the determination of the activity and stereoselectivity of enzymes, and presents an approach producing key intermediates of chiral drugs with practical potential. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9SDS of cas: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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.SDS of cas: 120121-01-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

On-DNA Hydroalkylation to Introduce Diverse Bicyclo[1.1.1]pentanes and Abundant Alkyls via Halogen Atom Transfer was written by Yen-Pon, Expedite;Li, Longbo;Levitre, Guillaume;Majhi, Jadab;McClain, Edward J.;Voight, Eric A.;Crane, Erika A.;Molander, Gary A.. And the article was included in Journal of the American Chemical Society in 2022.Formula: C9H17NO3 This article mentions the following:

A Giese addition to install highly functionalized bicyclo[1.1.1]pentanes (BCPs) using tricyclo[1.1.1.01,3]pentane (TCP) as a radical linchpin, as well as other diverse alkyl groups, on-DNA from the corresponding organohalides as non-stabilized radical precursors was reported. Telescoped procedures allow extension of the substrate pool by at least an order of magnitude to ubiquitous alcs. and carboxylic acids, allowing us to “upcycle” these abundant feedstocks to afford non-traditional libraries with different physicochem. properties for the small-mol. products (i.e., non-peptide libraries with acids). This approach is amenable to library production, as a DNA damage assessment revealed good PCR amplifiability and only 6% mutated sequences for a full-length DNA tag. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Formula: C9H17NO3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) 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.Formula: C9H17NO3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chemical profiling, antioxidant, enzyme inhibitory and in silico modeling of Rosmarinus officinalis L. and Artemisia herba alba Asso. essential oils from Algeria was written by Amina, Benabdallah;Soumeya, Betina;Salim, Bouchentouf;Mahieddine, Boumendjel;Sakina, Bechkri;Chawki, Bensouici;Francesca, Nicoli;Marzia, Vergine;Carmine, Negro;Luigi, De Bellis. And the article was included in South African Journal of Botany in 2022.Application In Synthesis of 5-Isopropyl-2-methylphenol This article mentions the following:

In the current study, the chem. composition, antioxidant, α-glucosidase, α-amylase and cholinesterase inhibitory activities of wormwood and rosemary essential oils were investigated. In order to explain the interaction of chem. constituents with the enzymes, mol. docking tools were used. GC/MS analyses revealed that the main compounds of rosemary oil were eucalyptol (37.97%), followed by camphor (11.84%). Whereas β-copaene (16.22%), limonene (14.56%), eucalyptol (14.49%) and camphor (13.74%) represent the main compounds of wormwood oil. Moreover, antioxidant abilities assessed by DPPH radical scavenging, β-carotene bleaching inhibitory and ion chelating test showed that rosemary oil was more efficient than wormwood. Furthermore, rosemary oil exhibited even better results against cholinesterase inhibitory. However, wormwood oil was more effective for antidiabetic inhibitory enzymes. The theor. verification by mol. modeling revealed that linalool, terpinen-4-ol, eugenol Me ether and Τ-cadinol have the best binding affinity with studied enzymes. In conclusion, docking verification has shown a good affinity of some chem. compounds from rosemary more than wormwood with studied enzymes explaining the assessed biol. activities. Rosemary and wormwood exhibited interesting biol. activities that explain the traditional uses of these plants that could be further explored for food and pharmaceutical industries. In the experiment, the researchers used many compounds, for example, 5-Isopropyl-2-methylphenol (cas: 499-75-2Application In Synthesis of 5-Isopropyl-2-methylphenol).

5-Isopropyl-2-methylphenol (cas: 499-75-2) 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. 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.Application In Synthesis of 5-Isopropyl-2-methylphenol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electrophotocatalytic Si-H activation governed by polarity-matching effects was written by Jiang, Yangye;Xu, Kun;Zeng, Chengchu. And the article was included in CCS Chemistry in 2022.Related Products of 2216-51-5 This article mentions the following:

Trialkylsilanes are important building blocks in organic synthesis; however, their widespread use in redox chem. is limited by their high oxidation potentials and comparably high bond dissociation energies (BDEs) of Si-H and α-Si-C-H bonds (>92 kcal mol-1). Herein, we report a new strategy for Si-H bond homolysis enabled by the synergistic combination of electrooxidation, photoinduced ligand-to-metal charge transfer (LMCT), and radical-mediated hydrogen atom transfer (HAT). Governed by the polarity-matching effect, the HAT to electrophilic MeO· or [Cl-OHCH₃]· from the more hydridic Si-H instead of a C-H bond allows the selective generation of silyl radicals. This electrophotocatalytic protocol provides rapid access to Si-functionalized benzimidazo-fused isoquinolinones with broad functional-group compatibility. Mechanistic studies have shown that n-Bu4NCl is essential to the electrooxidation of CeCl₃ to form the Ce(IV) species. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Related Products of 2216-51-5).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) 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. 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.Related Products of 2216-51-5

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gold-Catalyzed Cyclization of Ynones Involving cis-Hydrofunctionalizations: Rapid Assembly of C-, O-, or S-Functionalized Pyrroles by a Single Methodology was written by Pei, Miaomiao;Wang, Ali;Xie, Xin;Hu, Xiaoping;Liu, Yuanhong. And the article was included in Organic Letters in 2022.Synthetic Route of C10H20O This article mentions the following:

A gold-catalyzed cyclization of conjugated ynones with various nucleophiles such as indoles, alcs. and thiols was developed. The reaction provided a new and efficient protocol for the synthesis of functionalized pyrroles with wide versatility and functional group compatibility. Remarkably, indolyl, alkoxy or sulfenyl pyrroles, all could be constructed efficiently by this single methodol. In addition, cis-hydrofunctionalizations of ynones were involved in these reactions. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Synthetic Route of C10H20O).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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.Synthetic Route of C10H20O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Transformations of P-chalcogenide precursors with a hydrated metal salt was written by Shi, Weifeng;Kelting, Rebecca;Shafaei-Fallah, Maryam;Rothenberger, Alexander. And the article was included in Journal of Organometallic Chemistry in 2007.Quality Control of Sodium 2-methyl-2-propanethiolate This article mentions the following:

The preparation, characterization and x-ray structures of the three Ni(II) complexes [Ni{ArP(OH)S₂}₂(THF)₂] (1) (Ar = 4-anisyl), [Ni{PhP(OH)Se₂}₂(THF)₂] (2) and [Ni{P(OH)₂S₂}₂(THF)₄] (3) are reported. The crystal structures of 1–3 were determined In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Quality Control of Sodium 2-methyl-2-propanethiolate).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) 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. 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.Quality Control of Sodium 2-methyl-2-propanethiolate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Facile Access to Challenging ortho-Terphenyls via Merging Two Multi-Step Domino Reactions in One-Pot: A Joint Experimental/Theoretical Study was written by Grau, Benedikt W.;Boenisch, Simon;Neuhauser, Alexander;Hampel, Frank;Goerling, Andreas;Tsogoeva, Svetlana B.. And the article was included in ChemCatChem in 2019.Related Products of 2968-93-6 This article mentions the following:

A straightforward and sustainable synthesis of highly functionalized ortho-terphenyls I (R = CN, ethoxycarbonyl; R¹ = H, F, OMe, Me, etc.; Ar = Ph, furan-3-y, 4-(diphenylamino)phenyl, etc.) via joining an organocatalyzed two-step domino reaction (Knoevenagel/vinylogous Michael) with a DABCO/CuBr₂ co-catalyzed three-step domino reaction (cyclization/tautomerization/aromatization) in a one-pot process was demonstrated. Overcoming necessity to isolate intermediate products leads to a reduction of energy, costs and waste for a broad scope of reactions. DFT calculations have been performed to investigate the thermodn. of this one-pot process towards ortho-terphenyls I and to study the reaction profile of the vinylogous Michael reaction under inclusion of solvent effects. Role of London dispersion forces in this transformation has been elucidated. It is shown that reaction kinetics and thermodn. are slightly influenced by dispersion interactions. Furthermore, the addition of dispersion energy donors leads to small changes of reaction energies in some cases. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Related Products of 2968-93-6).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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.Related Products of 2968-93-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reaction of aliphatic diazo compounds with unsaturated compounds. XXIV. Reaction of diazoacetic ester with 5-decyne and 4-octyne. Effect of the nature and amount of the catalyst on orientation of the reaction was written by Komendantov, M. I.;D’yakonov, I. A.;Gokhmanova, I.;Kostikov, R. R.. And the article was included in Zhurnal Organicheskoi Khimii in 1965.SDS of cas: 1634-34-0 This article mentions the following:

5-Decyne (30 g.) and 0.05 g. CuSO₄ was treated at 90° with 12 g. EtO₂CCHN₂ over 3 hrs. and gave 12% di-Et fumarate and 39.1% Et 1,2-dibutylcyclopropene-3-carboxylate (I), b₃ 89-90°, d₂₀ 0.8965, ν²⁰_D 1.44523, n²⁰_D 1.44786, n²⁰_F 1.45424. The yield of I rose to 43% with Bz₂O₂ catalyst, but the mixture required 2-3 hrs. addnl. heating; Cu gave 35.7% yield, CuO 10%, Cu(OAc)₂, CUCl, Cu stearate and Cu(NO₃)₂ were ineffective; without the catalyst, the yield was 19.3%. For best yield (51.6%) the CuSO₄ catalyst must comprise 2.15 moles per 1000 moles of 5-decyne. I heated 8 hrs. with MeONaMeOH gave 83% 1,2-dibutyl-1(2)-cyclopropene-3-carboxylic acid, b₃ 121-2°, 0.9329, 1.45842, 1.46120, 1.46808 (oxidized with KMnO₄ it gave divalerylmethane, b₅ 97-8°). When the condensation with 5-decyne was run with 2.91 moles CuSO₄ per 1000 moles alkyne, the reaction gave up to 83.8% 2,3-dibutyl-5-ethoxyfuran (II), b₃ 104-5°, 0.9113, 1.45599, 1.45894, 1.46624, which with maleic anhydride in 0.5 hr. at 100° gave 2,5-endoxo-1,2-dibutyl-5-ethoxy-6-cyclohexene-3,4-dicarboxylic anhydride, m. 146-8°, or 1,2-dibutyl-5-ethoxybenzene-3,4-dicarboxylic anhydride, m. 107-8°, depending on the reactant ratio. II treated with O in heptane at room temperature gave after warming with H₂O 2 hrs. 56.2% Et 3-butyl-2-octen-4-on-1-oate, b_0.3 97-9°, d₂₀ 0.9746, n²⁰_D 1.4638, which with MeOH-KOH 2 hrs. gave the free acid (III), b_0.3 123-4°, 0.9936, 1.4625. II and aqueous alc. HCl 2 hrs. under N gave 70.4% 2.3-dibutyl-2,5-dihydro-5-furanone, b_0.3 96-8°, 0.9556, 1.4662, which in 30% KOH in MeOH 1 hr. gave 3-butyl-4-octanon-1-oic acid, b_0.3 121-2°, 0.9745, 1.4498 (semicarbazone m. 154-5°), also formed by hydrogenation of III over Pd-CaCO₃ in EtOH. EtO₂CCHN₂ and 4-octyne, as above with CuSO₄, gave up to 42% Et 1,2-dipropyl-1(2)-cyclopropene-3-carboxylate, b₃ 78-9°, 0.9053, n²⁰_D 1.44253, n²⁰_D 1.44513, n²⁰_F 1.45160; with Cu catalyst the yield was 51%, while without a catalyst at 135-40° the reaction gave 23.3% yield. The ester was saponified with MeONa-MeOH to the free acid, b₁ 92-3°, 0.9636, 1.45951, 1.46249, 1.46990 (oxidized with KMnO₄ it gave dibutyrylmethane). With larger amount CuSO₄ catalyst there was obtained some di-Et fumarate and 53.3% 2,3-dipropyl-5-ethoxyfuran, b₅ 86-7°, 0.92528, 1.45588, 1.45900, 1.46646. This and maleic anhydride gave 1,2-dipropyl-5-ethoxybeuzene-3,4-dicarboxylic anhydride, m. 133-4°. In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0SDS of cas: 1634-34-0).

2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. 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.SDS of cas: 1634-34-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Radical cascade synthesis of azoles via tandem hydrogen atom transfer was written by Chen, Andrew D.;Herbort, James H.;Wappes, Ethan A.;Nakafuku, Kohki M.;Mustafa, Darsheed N.;Nagib, David A.. And the article was included in Chemical Science.Application In Synthesis of 2-(Trifluoromethyl)phenethyl alcohol This article mentions the following:

A radical cascade strategy for the modular synthesis of five-membered heteroarenes (e.g. oxazoles, imidazoles) I (R¹ = Ph, 4-MeOC₆H₄, 4-F₃C₆H₄, 2-naphthyl, biphenyl-4-yl, etc.; R² = Ph, 2-pyridinyl, 4-IC₆H₄, 3-MeC₆H₄, etc.), II (R³ = 4-F₃CC₆H₄, CCl₃) from feedstock reagents (e.g. alcs., (R²CH₂CH₂OH), amines (such as., benzylamine, morpholine, pyrrolidine), nitriles R¹CN) has been developed. This double C-H oxidation is enabled by in situ generated imidate R¹C(=N)OCH₂CH₂R² and acyloxy radicals, which afford regio- and chemo-selective β C-H bis-functionalization. The broad synthetic utility of this tandem hydrogen atom transfer (HAT) approach to access azoles is included, along with experiments and computations that provide insight into the selectivity and mechanism of both HAT events. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5Application In Synthesis of 2-(Trifluoromethyl)phenethyl alcohol).

2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. 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.Application In Synthesis of 2-(Trifluoromethyl)phenethyl alcohol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts