Tag: 100-200

On September 17, 2001, Stavenger, Robert A.; Schreiber, Stuart L. published an article.SDS of cas: 929-37-3 The title of the article was Asymmetric catalysis in diversity-oriented organic synthesis: Enantioselective synthesis of 4320 encoded and spatially segregated dihydropyrancarboxamides. And the article contained the following:

Dihydropyrancarboxylates were prepared on solid-phase by stereoselective and enantioselective hetero Diels-Alder cycloaddition of β,γ-unsaturated-α-keto esters to resin-bound vinyl ethers in the presence of nonracemic copper bis(oxazoline) catalysts as intermediates in the preparation of an encoded combinatorial library of dihydropyrancarboxamides. Hydroxy-substituted vinyl ethers were prepared; the vinyl ethers were attached by treatment of silyl-substituted polystyrene resin macrobeads with triflic acid followed by addition of the hydroxy-substituted vinyl ethers to the resin-bound silyl triflate; the resin-bound vinyl ethers were treated with chloroarom. diazoketones in the presence of dirhodium tetraacetate to give tagged resin-bound vinyl ethers which could be later identified by LC-MS. Treatment of resin-bound vinyl ethers such as I with the heterodienes (E)-RCH:CHCOCO2CH2CH:CH2 (R = Me2CH, Ph, 2-fluorenyl, 4-MeO2CC6H4, 5-benzo-1,3-dioxolanyl, 3-thienyl, 3-benzofuranyl, 1-acetyl-3-indolyl, 4-oxo-3-benzopyranyl, 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydropyrazolyl) in the presence of the bis(oxazoline) II (or its enantiomer) and copper (II) triflate followed by cleavage of the resin with HF•pyridine gives nonracemic dihydropyrancarboxylates such as III (or their enantiomers) in >5:1 diastereoselectivities and >30:1 enantioselectivities. The resin-bound dihydropyrancarboxylates could be tagged with a second chloroarom. diazoketone, deallylated with tetrakis(triphenylphosphine)palladium and thiosalicylic acid in THF, coupled with primary and secondary amines with the benzotriazolyloxyphosphonium salt PyBOP and diisopropylethylamine, and cleaved from the resin with HF•pyridine to give an encoded combinatorial library of natural product-like nonracemic dihydropyrancarboxamides (no data). E.g., treatment of the silyl-substituted polystyrene resin with triflic acid followed by the addition of sulfonamide-substituted vinyl ether I with lutidine gave a resin-bound vinyl ether; the vinyl ether resin was added to unsaturated ketoester (E)-Me2CHCH:CHCOCO2CH2CH:CH2 and mol. sieves under argon; addition of THF and a solution of II and copper triflate in THF and stirring gave a resin-bound nonracemic dihydropyrancarboxylate which was cleaved from the resin with HF•pyridine to give III in >95% purity and in >16:1 diastereo- and enantioselectivities. Cleavage of a subset of the dihydropyrancarboxamide-containing beads and anal. by LC-MS indicated that 104 of the 108 sample compounds were isolated in >75% purity. The use of asym. synthesis of natural product-like libraries on encoded beads allows for the use of stereochem. as a diversity element in the preparation of combinatorial libraries; the prepared libraries are produced in a form amenable to robot-controlled biol. testing. The experimental process involved the reaction of 2-(2-(Vinyloxy)ethoxy)ethanol(cas: 929-37-3).SDS of cas: 929-37-3

The Article related to dihydropyrancarboxylate stereoselective enantioselective preparation intermediate combinatorial library, dihydropyrancarboxamide stereoselective enantioselective preparation combinatorial library, copper bisoxazoline catalyst enantioselective cycloaddition unsaturated ketoester vinyl ether and other aspects.SDS of cas: 929-37-3

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Brown, Ryan K.; Hooper, Thomas N.; Rekhroukh, Feriel; White, Andrew J. P.; Costa, Paulo J.; Crimmin, Mark R. published an article in 2021, the title of the article was Alumination of aryl methyl ethers: switching between sp2 and sp3 C-O bond functionalisation with Pd-catalysis.Name: 1,2-Dimethoxybenzene And the article contains the following content:

The reaction of aluminum(I) β-diketiminate [(ArN:CMeCHCMe:NAr)Al] (Ar = 2,6-iPr2C6H3) with aryl Me ethers proceeded with alumination of the sp3 C-O bond. The selectivity of this reaction could be switched by inclusion of a catalyst. In the presence of [Pd(PCy3)2], chemoselective sp2 C-O bond functionalization was observed Kinetic isotope experiments and DFT calculations support a catalytic pathway involving the ligand-assisted oxidative addition of the sp2 C-O bond to a Pd-Al intermetallic complex. The experimental process involved the reaction of 1,2-Dimethoxybenzene(cas: 91-16-7).Name: 1,2-Dimethoxybenzene

The Article related to aluminum subvalent diketiminate oxidative addition phenol benzyl ether, carbon oxygen bond chemoselective activation phenyl benzyl ether, organoaluminum diketiminate preparation oxidative addition aryl benzyl alkyl ether, crystal mol structure aluminum alkoxide diketiminate aryl complex and other aspects.Name: 1,2-Dimethoxybenzene

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Ether – Wikipedia,
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On April 28, 2021, Nilova, Aleksandra; Sibbald, Paul A.; Valente, Edward J.; Gonzalez-Montiel, Gisela A.; Richardson, H. Camille; Brown, Kevin S.; Cheong, Paul Ha-Yeon; Stuart, David R. published an article.Synthetic Route of 321-28-8 The title of the article was Regioselective Synthesis of 1,2,3,4-Tetrasubstituted Arenes by Vicinal Functionalization of Arynes Derived from Aryl(Mes)iodonium Salts. And the article contained the following:

Herein, the synthesis of 1,2,3,4-tetrasubstituted benzenoid rings, motifs found in pharmaceutical, agrochem., and natural products, is described. In the past, the regioselective syntheses of such compounds have been a significant challenge. This work reports a method using substituted arynes derived from aryl(Mes)iodonium salts to access a range of densely functionalized 1,2,3,4-tetrasubstituted benzenoid rings. Significantly, it was found that halide substituents are compatible under these conditions, enabling post-synthetic elaboration via palladium-catalyzed coupling. This concise strategy is predicated on two regioselective events: 1) ortho-deprotonation of aryl(Mes)iodonium salts to generate a substituted aryne intermediate, and 2) regioselective trapping of said arynes, thereby improving previously reported reaction conditions to generate arynes at room temperature and in shorter reaction times. D. functional theory (DFT) computations and linear free energy relationship (LFER) anal. suggest the regioselectivity of deprotonation is influenced by both proximal and distal ring substituents on the aryne precursor. A competition experiment further reveals the role of arene substituents on relative reactivity of aryl(Mes)iodoniums as aryne precursors. The experimental process involved the reaction of 1-Fluoro-2-methoxybenzene(cas: 321-28-8).Synthetic Route of 321-28-8

The Article related to tetrasubstituted arene preparation regioselective transition state structure dft, aryl mesyl iodonium tosylate aryne arylation, substituent effect linear free energy relationship regioselectivity aryne formation, arylation, aryne, deprotonation, diaryliodonium salt, hypervalent iodine and other aspects.Synthetic Route of 321-28-8

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Ether – Wikipedia,
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On May 11, 2020, Gevorgyan, Ashot; Hopmann, Kathrin H.; Bayer, Annette published an article.Reference of 1,2-Dimethoxybenzene The title of the article was Formal C-H Carboxylation of Unactivated Arenes. And the article contained the following:

A formal C-H carboxylation of unactivated arenes e.g., I using CO2 in green solvents is described. The present strategy combines a sterically controlled Ir-catalyzed C-H borylation followed by a Cu-catalyzed carboxylation of the in situ generated organoboronates. The reaction is highly regioselective for the C-H carboxylation of unactivated arenes e.g., I (1,3-disubstituted and 1,2,3-trisubstituted benzenes, 1,2- or 1,4-sym. substituted benzenes, fluorinated benzenes and different heterocycles). The developed methodol. was applied to the late-stage C-H carboxylation of com. drugs and ligands. The experimental process involved the reaction of 1,2-Dimethoxybenzene(cas: 91-16-7).Reference of 1,2-Dimethoxybenzene

The Article related to carboxyl unactivated arene preparation green chem regioselective, unactivated arene carbon dioxide carboxylation copper catalyst, carbon dioxide aryl boronate carboxylation copper catalyst, c−h activation, carbon dioxide, carboxylation, green solvent, late-stage functionalization and other aspects.Reference of 1,2-Dimethoxybenzene

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

On May 11, 2020, Gevorgyan, Ashot; Hopmann, Kathrin H.; Bayer, Annette published an article.Category: ethers-buliding-blocks The title of the article was Formal C-H Carboxylation of Unactivated Arenes. And the article contained the following:

A formal C-H carboxylation of unactivated arenes e.g., I using CO2 in green solvents is described. The present strategy combines a sterically controlled Ir-catalyzed C-H borylation followed by a Cu-catalyzed carboxylation of the in situ generated organoboronates. The reaction is highly regioselective for the C-H carboxylation of unactivated arenes e.g., I (1,3-disubstituted and 1,2,3-trisubstituted benzenes, 1,2- or 1,4-sym. substituted benzenes, fluorinated benzenes and different heterocycles). The developed methodol. was applied to the late-stage C-H carboxylation of com. drugs and ligands. The experimental process involved the reaction of 1,4-Dimethoxybenzene(cas: 150-78-7).Category: ethers-buliding-blocks

The Article related to carboxyl unactivated arene preparation green chem regioselective, unactivated arene carbon dioxide carboxylation copper catalyst, carbon dioxide aryl boronate carboxylation copper catalyst, c−h activation, carbon dioxide, carboxylation, green solvent, late-stage functionalization and other aspects.Category: ethers-buliding-blocks

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

On December 31, 2021, Wang, Weijin; Li, Xinyao; Yang, Xiaoxue; Ai, Lingsheng; Gong, Zhiwen; Jiao, Ning; Song, Song published an article.Application In Synthesis of 2-Methoxynaphthalene The title of the article was Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics. And the article contained the following:

Herein, TEMPO (2,2,6,6-tetramethylpiperidine nitroxide) and its derivatives are disclosed as active catalysts for electrophilic halogenation of olefins e.., prop-1-en-1-ylbenzene, alkynes R1CCR2 (R1 = octyl, Ph; R2 = H, Me, n-Bu, Ph), and aromatics R3H (R3 = 3-(carboxymethyl)-4-methoxybenzen-1-yl, 2-[ethoxy(oxo)methane]-1H-indol-3-yl, 5-phenylthiophen-2-yl, etc.). These catalysts are stable, readily available, and reactive enough to activate haleniums including Br+, I+ and even Cl+ reagents. This catalytic system is applicable to various halogenations including haloarylation of olefins or dibromination of alkynes, which were rarely realized in previous Lewis base catalysis or Lewis acid catalysis. The high catalytic ability is attributed to a synergistic activation model of electrophilic halogenating reagents, where the carbonyl group and the halogen atom are both activated by present TEMPO catalysis. The experimental process involved the reaction of 2-Methoxynaphthalene(cas: 93-04-9).Application In Synthesis of 2-Methoxynaphthalene

The Article related to dibromoolefin preparation, olefin halogenation tetramethylpiperidine nitroxide catalyst, dibromoalkyne preparation, alkyne halogenation tetramethylpiperidine nitroxide catalyst, haloarene preparation regioselective, aromatic halogenation tetramethylpiperidine nitroxide catalyst and other aspects.Application In Synthesis of 2-Methoxynaphthalene

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

On November 11, 2010, Kanzawa, Keizo; Kawaguchi, Kenichi; Matsumoto, Shunichiro; Nomura, Takaho; Susumu, Takashi; Seo, Tatsushi published a patent.Category: ethers-buliding-blocks The title of the patent was Preparation of azolecarboxamide compounds or their salts as antagonists of neurotrophic factor receptors (TrkA). And the patent contained the following:

N-Ph, N-pyridyl, or N-pyrazolylthiazole-4-carboxamides and oxazole-4-carboxamides the title compounds [I; X = S, O; R1 = Q, Q1, 3-methoxymethylmorpholin-4-yl, NR1cR1d; R1a = H, HO, lower alkoxy, cycloalkyloxy; R1b = H, lower alkoxy; R1c = H, lower alkyl; R1d = lower alkyl optionally substituted by lower alkoxy; R2 = H, lower alkyl optionally substituted by F or lower alkoxy, 3-tetrahydrofuryl, 4-tetrahydropyranyl; A = R2, Q3, Q4; R3 = CO2Me, Q5, CH2R3B; R00 = lower alkyl; R3B = OH, lower alkoxy, Q6, Q7, Q8, Q10, hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl; R0 = H, lower alkyl; m = 1,2; Ra = H, F, Ph, lower alkoxy-lower alkyl; R4 = lower alkyl optionally substituted by lower alkoxy] or salts thereof are prepared These compounds possess potent inhibitory activity against neurotrophic factor receptors (TrkA) and provide therapeutic and/or preventive agents for various lower urinary tract diseases accompanied by lower urinary tract pains such as interstitial cystitis and chronic prostatitis, urinary frequency accompanied by various lower urinary tract diseases including overactive bladder, feeling of micturition urgency, urinary incontinence, and various diseases accompanied by pain based on the TrkA-inhibitory activity. Thus, 67 mg (8aR)-octahydropyrrolo[1,2-a]pyrazine and 216 mg Cs2CO3 were added to a mixture of 200 mg N-[4-(chloromethyl)-2-[(2-methoxyethyl)carbamoyl]phenyl]-2-((3S)-3-methoxypyrrolidin-1-yl)-1,3-thiazole-4-carboxamide and 2 mL DMF and the resulting mixture was stirred at room temperature for 18 h to give, after workup and silica gel chromatog. and salt formation with fumaric acid, N-[4-[((8aR)-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-2-[(2-methoxyethyl)carbamoyl]phenyl]-2-((3S)-3-methoxypyrrolidin-1-yl)-1,3-thiazole-4-carboxamide (II) difumarate. II difumarate and N-phenylthiazole-4-carboxamide derivative (III) in vitro inhibited the NGF-induced increase in cellular calcium ion in HEK293 cells stably expressing human trkA receptor with IC50 of 19 and 16 nM, resp. The experimental process involved the reaction of (S)-1-Methoxypropan-2-amine hydrochloride(cas: 1162054-86-5).Category: ethers-buliding-blocks

The Article related to azolecarboxamide preparation antagonist neurotrophic factor receptor trka, thiazolecarboxamide oxazolecarboxamide preparation antagonist neurotrophic factor receptor trka, pain urinary tract disease treatment prevention thiazolecarboxamide oxazolecarboxamide preparation and other aspects.Category: ethers-buliding-blocks

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

Wu, Zhuo; Jiang, Hang; Zhang, Yanghui published an article in 2021, the title of the article was Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated via C(sp3)-H activation.Reference of 2-Methoxynaphthalene And the article contains the following content:

Pd-catalyzed cascade cross-electrophile coupling and C-H alkylation reaction of 2-iodo-alkoxylarenes with alkyl chlorides were reported. Methoxy and benzyloxy groups, which were ubiquitous functional groups and common protecting groups, were utilized as crucial mediators via primary or secondary C(sp3)-H activation. The reaction provided an innovative and convenient access for the synthesis of alkylated phenol derivatives, which were widely found in bioactive compounds and organic functional materials. The experimental process involved the reaction of 2-Methoxynaphthalene(cas: 93-04-9).Reference of 2-Methoxynaphthalene

The Article related to methoxy alkylarene preparation regioselective, haloalkane methoxy aryliodide palladium tandem alkylation oxidative cross coupling, benzyloxy alkylbenzene preparation regioselective, phenyl benzyloxyiodide haloalkane palladium tandem alkylation oxidative cross coupling and other aspects.Reference of 2-Methoxynaphthalene

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

On May 31, 2022, Yerien, Damian E.; Barata-Vallejo, Sebastian; Mansilla, Daniela; Postigo, Al published an article.COA of Formula: C8H10O2 The title of the article was Rose Bengal-photocatalyzed perfluorohexylation reactions of organic substrates in water. Applications to late-stage syntheses. And the article contained the following:

Rose Bengal-photocatalyzed perfluorohexylation of olefins, alkynes and electron-rich aromatic compounds in water was achieved employing perfluorohexyl iodide as fluoroalkyl source and TMEDA as sacrificial donor under green LED irradn to afford perfluoro compounds R1CHICH2C6F13 [R1 = CH2OPh, CHOH(CH2)5], R2HC=CHC6F13 [R2 = Ph, n-pentyl, (D)-(-)Norgestreyl] and I [R3 = 4-Me, 4-NO2, 2,6-(Me)2, etc.; R4 = OMe, NH2]. Alkenes and alkynes rendered products derived from the atom transfer radical addition (ATRA) pathway, and in the case of alkynes, exclusively as E-stereoisomers. These were the first examples of photocatalyzed ATRA reactions carried out excursively in water alone. The reactions of aromatic compounds under the current protocol in water present the advantage of employing a perfluoroalkyl iodide (C6F13-I) as source of perfluorohexyl radicals. Examples of photocatalytic late-stage incorporations of fluoroalkyl moieties into two com. drugs of widespread used were reported. The experimental process involved the reaction of 1,2-Dimethoxybenzene(cas: 91-16-7).COA of Formula: C8H10O2

The Article related to perfluoro compound green preparation, alkene perfluorohexylation rose bengal photocatalyst, alkyne perfluorohexylation rose bengal photocatalyst, aromatic compound perfluorohexylation rose bengal photocatalyst, late-stage perfluoroalkylation, perfluoroalkylation of alkynes, perfluoroalkylation of arenes, perfluoroalkylation of olefins, photocatalysis in water and other aspects.COA of Formula: C8H10O2

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

Dong, Jinhuan; Xin, Shuang; Wang, Yanqing; Pan, Ling; Liu, Qun published an article in 2017, the title of the article was In situ generation and reactions of p-(trifluoromethyl)benzyl electrophiles: an efficient access to p-(trifluoromethyl)benzyl compounds.Recommanded Product: 1-Fluoro-2-methoxybenzene And the article contains the following content:

A new three-component reaction, namely condensation-anti-Michael addition-aromatization, enabling the construction of benzylic compounds was disclosed. This reaction not only acted as an alternative approach to regioselective Csp2-H trifluoromethylation of arenes through an “aromatic to be” strategy, but also provided a simple, convenient, step-economic and practical strategy for the in-situ generation of electrophilic p-(trifluoromethyl)benzyl species under extremely mild conditions. The experimental process involved the reaction of 1-Fluoro-2-methoxybenzene(cas: 321-28-8).Recommanded Product: 1-Fluoro-2-methoxybenzene

The Article related to trifluoromethyl trimethylsilyloxycyclohexadienone ketone sulfonamide indium triflate catalyst tandem reaction, trifluoromethylbenzylamine regioselective preparation arene, methane diaryl preparation regioselective, arene trifluoromethyl trimethylsilyloxycyclohexadienone ketone indium triflate catalyst tandem reaction, diarylmethane preparation regioselective and other aspects.Recommanded Product: 1-Fluoro-2-methoxybenzene

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