Tag: 100-200

Zhang, Feng-Hua; Guo, Xiaochong; Zeng, Xianrong; Wang, Zhaobin published an article in 2022. The article was titled 《Catalytic Enantioconvergent Allenylation of Aldehydes with Propargyl Halides》, and you may find the article in Angewandte Chemie, International Edition.Category: ethers-buliding-blocks The information in the text is summarized as follows:

The Cr-catalyzed enantioconvergent allenylation of aldehydes with racemic propargyl halides to rapidly access a wide range of chiral α-allenols with adjacent axial and central chiralities. This method featured excellent regio-, diastereo- and enantioselectivity control with broad substrate scope, and provides facile access to all four stereoisomers when allied with a Mitsunobu reaction. Preliminary mechanistic studies supported radical-based reaction pathways. The synthetic utility was demonstrated by the application in late-stage functionalization and the formal total synthesis of (+)-varitriol. In the experimental materials used by the author, we found 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Category: ethers-buliding-blocks)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) may be used in the following syntheses: (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate ,(S)-5-benzyloxy-4-hydroxypentan-2-one, myxothiazols.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Min, Xiang-Ting; Mei, Yong-Kang; Chen, Bing-Zhi; He, Li-Bowen; Song, Ting-Ting; Ji, Ding-Wei; Hu, Yan-Cheng; Wan, Boshun; Chen, Qing-An published an article in 2022. The article was titled 《Rhodium-Catalyzed Deuterated Tsuji-Wilkinson Decarbonylation of Aldehydes with Deuterium Oxide》, and you may find the article in Journal of the American Chemical Society.Electric Literature of C9H10O2 The information in the text is summarized as follows:

The recent surge in the applications of deuterated drug candidates has rendered an urgent need for diverse deuterium labeling techniques. Herein, an efficient Rh-catalyzed deuterated Tsuji-Wilkinson decarbonylation of naturally available aldehydes with D2O is developed. In this reaction, D2O not only acts as a deuterated reagent and solvent but also promotes Rh-catalyzed decarbonylation. In addition, decarbonylative strategies for the synthesis of terminal monodeuterated alkenes from α,β-unsaturated aldehydes are within reach. The experimental part of the paper was very detailed, including the reaction process of 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Electric Literature of C9H10O2)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) may be used in the following syntheses: (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate ,(S)-5-benzyloxy-4-hydroxypentan-2-one, myxothiazols.Electric Literature of C9H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Brzeskiewicz, Jakub; Stanska, Barbara; Dabrowski, Piotr; Loska, Rafal published an article in 2021. The article was titled 《C-H Activation and Cross-Coupling of Acyclic Aldonitrone》, and you may find the article in European Journal of Organic Chemistry.Quality Control of 1-Bromo-3-methoxybenzene The information in the text is summarized as follows:

Palladium-catalyzed activation of C(sp2)-H bond in a readily E,Z-isomerizable aldonitrone, bearing an ester group at the C terminus, enabled its cross-coupling with a variety of aryl and heteroaryl bromides to give ketonitrones, including products with functional groups not compatible with the classical nitrone synthesis via condensation with hydroxylamines. The reactions proceeded with very high (usually complete) E selectivity. The key to obtaining good yields of the cross-coupling products was the use of sterically hindered carboxylic acid as additive and non-polar solvent (toluene), in which the starting nitrone exists mainly as E isomer. Further use of the obtained ketonitrones in dipolar cycloaddition or nucleophilic addition has also been demonstrated.1-Bromo-3-methoxybenzene(cas: 2398-37-0Quality Control of 1-Bromo-3-methoxybenzene) was used in this study.

1-Bromo-3-methoxybenzene(cas: 2398-37-0) can be used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.Quality Control of 1-Bromo-3-methoxybenzene

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Moraes, Maiara C.; Lenardao, Eder J.; Barcellos, Thiago published their research in ARKIVOC (Gainesville, FL, United States) in 2021. The article was titled 《Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis》.SDS of cas: 150-19-6 The article contains the following contents:

A series of functionalized C4-substituted coumarins were synthesized by exploring the reaction of activated and non-activated phenols and β-ketoesters under solvent-free conditions in the presence of sulfamic acid as a Bronsted acid catalyst. Fifteen examples were prepared with moderate to excellent yields (50% to 90%) using 10 mol % of the catalyst. Furthermore, it was possible from the proposed methodol. to scale up the synthesis of coumarins to obtain up to 11 g of product. This work also provides a preliminary insight into the reaction mechanism using high-resolution mass spectrometry anal. The key cinnamic acid derivative intermediate was detected, implying that under the evaluated conditions, the mechanistic pathway starts with an aromatic electrophilic substitution followed by dehydration reaction and intramol. transesterification. In the part of experimental materials, we found many familiar compounds, such as m-Methoxyphenol(cas: 150-19-6SDS of cas: 150-19-6)

m-Methoxyphenol(cas: 150-19-6) may be used in synthesis of:C(4) symmetric calix[4]resorcinarene, 2-nitroso-5-methoxyphenol, 6-methoxy-2(3H)-benzoxazoloneSDS of cas: 150-19-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Karale, Uttam B.; Shinde, Akash U.; Babar, Dattatraya A.; Sangu, Komal G.; Vagolu, Siva Krishna; Eruva, Vamshi K.; Jadav, Surender S.; Misra, Sunil; Dharmarajan, Sriram; Rode, Haridas B. published their research in Archiv der Pharmazie (Weinheim, Germany) in 2021. The article was titled 《3-Aryl-substituted imidazo[1,2-a]pyridines as antituberculosis agents》.Application In Synthesis of 1-Bromo-3-methoxybenzene The article contains the following contents:

3-Aryl-substituted imidazo[1,2-a]pyridines I [R1 = H, 6-Me, 7-Me, 8-Me; R2 = 4-tolyl, 2-naphthyl, 2-(4-methylanilino)-4-(trifluoromethyl)phenyl, etc.] were reported as potent antituberculosis agents. A small library of 3-aryl-substituted imidazo[1,2-a]pyridines I were synthesized using direct arylation followed by nitro reduction and finally Pd-catalyzed C-N coupling reactions. The compounds I thus obtained were evaluated against Mycobacterium tuberculosis H37Rv. Compound I [R1 = H, R2 = 3-cyanophenyl] was identified as an antituberculosis lead with a min. inhibitory concentration of 2.3μg/mL against M. tuberculosis H37Rv. This compound I [R1 = H, R2 = 3-cyanophenyl] showed a selectivity index of 35. The docking of compound I [R1 = H, R2 = 3-cyanophenyl] in the active site of the M. tuberculosis cytochrome bc1 complex cytochrome b subunit (Mtb QcrB) revealed key π-π interactions of I [R1 = H, R2 = 3-cyanophenyl] with the Tyr389 and Trp312 residues of Mtb QcrB. After reading the article, we found that the author used 1-Bromo-3-methoxybenzene(cas: 2398-37-0Application In Synthesis of 1-Bromo-3-methoxybenzene)

1-Bromo-3-methoxybenzene(cas: 2398-37-0) is a compound useful in organic synthesis and other chemical processes. It is an intermediate used for pharmaceuticals, perfumes and agrochemicals.Application In Synthesis of 1-Bromo-3-methoxybenzene

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The author of 《One step phenol synthesis from benzene catalysed by nickel(II) complexes》 were Muthuramalingam, Sethuraman; Anandababu, Karunanithi; Velusamy, Marappan; Mayilmurugan, Ramasamy. And the article was published in Catalysis Science & Technology in 2019. SDS of cas: 150-19-6 The author mentioned the following in the article:

Nickel(II)complexes of N4-ligands have been synthesized and characterized as efficient catalysts for the hydroxylation of benzene using H2O2. All the complexes exhibited Ni2+ → Ni3+ oxidation potentials of around 0.966-1.051 V vs. Ag/Ag+ in acetonitrile. One of the complexes has been structurally characterized and adopted an octahedral coordination geometry around the nickel(II) center. The complexes catalyzed direct benzene hydroxylation using H2O2 as an oxygen source and afforded phenol up to 41% with a turnover number (TON) of 820. This is unprecedentedly the highest catalytic efficiency achieved to date for benzene hydroxylation using 0.05 mol% catalyst loading and five equivalent of H2O2. The benzene hydroxylation reaction possibly proceeds via the key intermediate bis(μ-oxo)dinickel(III) species, which was characterized by HR-MS, vibrational and electronic spectral methods, for almost all complexes. The formation constant of the key intermediate was calculated to be 5.61-9.41 × 10-2 s-1 by following the appearance of an oxo-to-Ni(III) LMCT band at around 406-413 nm. The intermediates are found to be very short-lived (t1/2, 73-123 s). The geometry of one of the catalytically active intermediates was optimized by DFT and its spectral properties were calculated by TD-DFT calculations, which are comparable to exptl. spectral data. The kinetic isotope effect (KIE) values (0.98-1.05) support the involvement of nickel-bound oxygen species as an intermediate. The isotope-labeling experiments using H218O2 showed 92.46% incorporation of 18O, revealing that H2O2 is the key oxygen supplier to form phenol. The catalytic efficiencies of complexes are strongly influenced by the geometrical configuration of intermediates, and stereoelectronic and steric properties, which are fine-tuned by the ligand architecture. In addition to this study using m-Methoxyphenol, there are many other studies that have used m-Methoxyphenol(cas: 150-19-6SDS of cas: 150-19-6) was used in this study.

m-Methoxyphenol(cas: 150-19-6) may be used as an analytical standard for the determination of the analyte in wine, coffee beans, wood samples, and mainstream smoke by gas chromatography (GC) based techniques.SDS of cas: 150-19-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《(Di-tert-butylphosphinylethyl)cyclopentadienylnickel Chelates with Alkyl, Alkenyl, Aryl, and Alkynyl Ligands: Hints to Cumulenylidene Resonance Forms》 was published in European Journal of Inorganic Chemistry in 2018. These research results belong to Kohser, Stefanie; Butenschoen, Holger. COA of Formula: C12H10O2 The article mentions the following:

Cyclopentadienylalkylphosphine chelate complexes were studied in depth for many transition metals, but to a much lesser extent for Ni. From earlier studies of cyclopentadienylalkylphosphine Ni chelates, a number of new alkyl, aryl, alkenyl, and alkynyl complexes, including some bearing functional groups, were prepared and fully characterized. These include for the 1st time di- and trimetallic complexes as well as compounds with a ferrocene unit as part of the extended π system. A number of quaternized 2-pyridylethynyl complexes are presented, for which cyclovoltammograms, NMR spectroscopic data, and DFT calculations provide hints to a significant contribution of cumulenylidene resonance forms. In the part of experimental materials, we found many familiar compounds, such as 1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6COA of Formula: C12H10O2)

1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6) belongs to ethers.COA of Formula: C12H10O2Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Formula: C9H12O2On March 28, 1979, Kende, Andrew S.; Curran, Dennis P. published an article in Journal of the American Chemical Society. The article was 《Regiochemical control in dihydrophenanthrene synthesis. A photochemical total synthesis of juncusol》. The article mentions the following:

Three approaches are described toward the total synthesis of juncusol (I), a cytotoxic constituent of the needlerush Juncus roemerianus. Wittig condensation of the phosphonium salt derived from 2-methyl-3-methoxybenzyl bromide with 3-methoxy-4-methyl-5-cyanobenzaldehyde gave a mixture of cyanostilbenes, (E)- and (Z)-2,3-Me(MeO)C6H3CH:CHC6H2(CN)(OMe)Me-3,5,4. Reduction of this mixture gave the diarylethane, which failed to undergo oxidative aryl-aryl cyclization. Photocyclization of the stilbenes gave a 7:1 mixture of phenanthrenes in which the unwanted 7-cyano regioisomer predominated. The Ziegler modification of the Ullmann coupling was used to prepare the sym. dialdehyde II, which underwent successive Wittig reaction with Ph3P:CH2 and hydride reduction to give the key intermediate III. Photocyclization of III gave a dihydrophenanthrene alc. which underwent successive oxidation to an aldehyde, Wittig condensation with Ph3P:CH2, and demethylation to give I. The overall yield of I from 2-methyl-3-methoxybenzaldehyde is 18% over 10 steps; the route provides the first total synthesis of this natural product. The experimental part of the paper was very detailed, including the reaction process of (3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1Formula: C9H12O2)

(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1) belongs to ethers. Ethers lack the hydroxyl groups of alcohols. Formula: C9H12O2 Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Quality Control of 3-Methoxyphenylboronic acidIn 2021 ,《Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides and Primary Sulfonamides》 was published in Journal of the American Chemical Society. The article was written by Lo, Pui Kin Tony; Willis, Michael C.. The article contains the following contents:

A redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO) was developed to afford sulfonimidamides I [R = 2-MeC6H4, 4-FC6H4, 2-furyl, etc.; R1 = (CH2)2CN, pyrrolidin-1-yl, piperidin-1-yl, etc.] and primary sulfonamides II [R2 = 2-thienyl, 4-FC6H4, 4-MeOC6H4, etc.]. The reactions used a catalyst generated from the combination of com., air-stable NiCl2·(glyme) and a com. available bipyridine ligand. These transformations were all achieved using one-pot procedures. For larger-scale reactions, the catalyst loading could be reduced to 1 mol %. In addition to this study using 3-Methoxyphenylboronic acid, there are many other studies that have used 3-Methoxyphenylboronic acid(cas: 10365-98-7Quality Control of 3-Methoxyphenylboronic acid) was used in this study.

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.Quality Control of 3-Methoxyphenylboronic acid

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2022,Zhao, Yanliang; Wang, Honglei; Wu, Naiwei; Yang, Junxia; Sun, Jikai; Zhai, Dong; Deng, Weiqiao published an article in International Journal of Quantum Chemistry. The title of the article was 《The mechanism of sugar produced from simple glycolaldehyde derivative at ambient conditions》.Recommanded Product: 2-(Benzyloxy)acetaldehyde The author mentioned the following in the article:

A benchmark of sugar produced from simple glycolaldehyde derivative has been achieved at ambient conditions (Science, 2004, 305, 1752), which is the most important step to produce life in nature. However, the mechanism has never been clearly understood. Here, we report a reaction mechanism which includes a two-step synthesis of sugars by selective aldol reactions based on the d. functional theory (DFT) calculations Results show that the prochirality of attacking orientation of the enamine intermediate and steric effect in proton transfer is the main cause for stereochem. preference. This work provides the theor. insight of sugar produced in glycolaldehyde procedure and may assist the improvement of catalyst design for this procedure. After reading the article, we found that the author used 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Recommanded Product: 2-(Benzyloxy)acetaldehyde)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Recommanded Product: 2-(Benzyloxy)acetaldehyde

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem