Tag: 100-200

In 2022,Nicolaou, K. C.; Yu, Ruocheng; Lu, Zhaoyong; Alvarez, Fernando G. published an article in Journal of the American Chemical Society. The title of the article was 《Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations》.Quality Control of 2-(Benzyloxy)acetaldehyde The author mentioned the following in the article:

The synthesis of functionalized aromatic compounds is a central theme of research for modern organic chem. Despite the increasing finesse in the functionalization of five- and six-membered aromatic rings, their seven-membered-ring sibling, tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), remains a challenging target for synthetic derivatization. This challenge primarily emanates from the unique structural and chem. properties of tropolonoid compounds, which often lead to unexpected and undesired reaction outcomes under conditions developed for the functionalizations of other aromatic moieties. Herein, the authors describe the total synthesis of one of the most complex natural tropolonoids, gukulenin B (I). The synthetic route features a series of site-selective aromatic C-H bond functionalizations and C-C bond formations, whose reaction conditions are judiciously tuned to allow uncompromised performance on the tropolone nucleus. The flexibility and modularity of the synthesis are expected to facilitate further synthetic and biol. studies of the gukulenin family of cytotoxins. In addition, the methods and tactics developed herein for the functionalization of the tropolone moiety could inspire and enable chemists of multiple disciplines to take advantage of this privileged yet underexplored structural motif. In the part of experimental materials, we found many familiar compounds, such as 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Quality Control of 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).Quality Control of 2-(Benzyloxy)acetaldehyde

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

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

Referemce:
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

Quality Control of 2-(Benzyloxy)acetaldehydeIn 2020 ,《Ruthenium-Catalyzed Intermolecular Coupling of Vinylic 1,2-Bisboronates with Alkynes: Stereoselective Access to Boryl-Substituted Homoallylic Alcohols》 was published in Journal of the American Chemical Society. The article was written by Trost, Barry M.; Zhang, Guoting. The article contains the following contents:

The ruthenium catalytic addition of alkenes to alkynes has been demonstrated as a powerful synthetic tool to form diene motifs and widely applied in the synthesis of complex mols. However, except for the intramol. coupling, trisubstituted alkenes are unsatisfactory coupling partners with alkynes, presumably due to the increased steric hindrance. Herein, it is discovered that substituted vinyl 1,2-bisboronate derivatives can serve as the trisubstituted alkene equivalent to couple with alkynes, generating various boryl-substituted homoallylic alc. motifs with good stereoselectivity through the sequential allylboration with aldehydes. In contrast to carbon substituents on the double bond, boron substituents accelerate the alkyne coupling. In the part of experimental materials, we found many familiar compounds, such as 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Quality Control of 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).Quality Control of 2-(Benzyloxy)acetaldehyde

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

COA of Formula: C8H8O2In 2019 ,《Development of novel pyrazolones by using SiO2/ZnCl2 – green approach》 appeared in Journal of Chemical Sciences (Berlin, Germany). The author of the article were Neelima, G.; Lakshmi, K.; Sesha Maheswaramma, K.. The article conveys some information:

An efficient and green synthesis of substituted pyrazolone derivatives I [R = 2-MeO, 4-Cl, 3,4-di-MeO, etc.] was developed from 2,4-dinitrophenylhydrazine with aromatic aldehydes and Et acetoacetate in presence of silica-supported zinc chloride (SiO2/ZnCl2) as a recyclable Lewis acid catalyst. All the compounds I were tested for their antioxidant activity by using DPPH radical scavenging method. The results came from multiple reactions, including the reaction of 2-Methoxybenzaldehyde(cas: 135-02-4COA of Formula: C8H8O2)

2-Methoxybenzaldehyde(cas: 135-02-4) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma. It has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus putrescentiae.COA of Formula: C8H8O2

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

In 2022,Nicolaou, K. C.; Yu, Ruocheng; Lu, Zhaoyong; Alvarez, Fernando G. published an article in Journal of the American Chemical Society. The title of the article was 《Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations》.Quality Control of 2-(Benzyloxy)acetaldehyde The author mentioned the following in the article:

The synthesis of functionalized aromatic compounds is a central theme of research for modern organic chem. Despite the increasing finesse in the functionalization of five- and six-membered aromatic rings, their seven-membered-ring sibling, tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), remains a challenging target for synthetic derivatization. This challenge primarily emanates from the unique structural and chem. properties of tropolonoid compounds, which often lead to unexpected and undesired reaction outcomes under conditions developed for the functionalizations of other aromatic moieties. Herein, the authors describe the total synthesis of one of the most complex natural tropolonoids, gukulenin B (I). The synthetic route features a series of site-selective aromatic C-H bond functionalizations and C-C bond formations, whose reaction conditions are judiciously tuned to allow uncompromised performance on the tropolone nucleus. The flexibility and modularity of the synthesis are expected to facilitate further synthetic and biol. studies of the gukulenin family of cytotoxins. In addition, the methods and tactics developed herein for the functionalization of the tropolone moiety could inspire and enable chemists of multiple disciplines to take advantage of this privileged yet underexplored structural motif. In the part of experimental materials, we found many familiar compounds, such as 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Quality Control of 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).Quality Control of 2-(Benzyloxy)acetaldehyde

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