Category: 94-02-0

Huang, Zhiliang; Guan, Renpeng; Shanmugam, Muralidharan; Bennett, Elliot L.; Robertson, Craig M.; Brookfield, Adam; McInnes, Eric J. L.; Xiao, Jianliang published the artcile< Oxidative Cleavage of Alkenes by O2 with a Non-Heme Manganese Catalyst>, Safety of Ethyl 3-oxo-3-phenylpropanoate, the main research area is alkene oxygen light manganese oxidation catalyst; ketone preparation.

The oxidative cleavage of C=C double bonds with mol. oxygen to produce carbonyl compounds is an important transformation in chem. and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C=C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atm. pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asym., mixed-valent bis(�oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Journal of the American Chemical Society published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Safety of Ethyl 3-oxo-3-phenylpropanoate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Vereshchagin, Anatoly N.; Iliyasov, Taygib M.; Karpenko, Kirill A.; Smirnov, Vladimir A.; Ushakov, Ivan E.; Elinson, Michail N. published the artcile< Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines>, Electric Literature of 94-02-0, the main research area is tetrahydropyridine preparation diastereoselective; benzylidenemalononitrile oxocarboxylic acid aromatic aldehyde multicomponent heterocyclization ammonium acetate.

A novel four-component diastereoselective synthesis of polysubstituted tetrahydropyridines (4SR,6RS)-I (R = H, 3-F, 4-Me, 4-Cl, etc.; R1 = Me, Et, Ph, 4-bromophenyl; R2 = Me, Et) is reported. The Michael addition – Mannich reaction – cyclization – dehydration cascade of benzylidenemalononitriles RC6H4CH=C(CN)2, esters of 3-oxocarboxylic acids R1C(O)CH2C(O)OR2, aromatic aldehydes RC6H4CHO, and ammonium acetate in methanol provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine- 3-carboxylates (4SR,6RS)-I with two stereocenters in 66-92% yields. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays dual role acting as a base and as a nitrogen source. The formation of single diastereomer was confirmed by singe crystal X-ray diffraction studies.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Electric Literature of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Chan, Chieh-Kai; Lai, Chien-Yu; Wang, Cheng-Chung published the artcile< Environmentally Friendly Nafion-Mediated Friedlander Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones>, Formula: C11H12O3, the main research area is quinoline preparation green chem microwave irradiation; aminobenzophenone carbonyl synthon Friedlander reaction Nafion catalyst; quinolinyl chalcone preparation green chem microwave irradiation diastereoselective; benzaldehyde aminobenzophenone carbonyl synthon Friedlander reaction Nafion catalyst.

An efficient and eco-friendly synthetic route for Friedlander quinoline synthesis of polysubstituted quinolines e.g., I is described. This green chem. method starts from various 2-aminobenzophenones 2-NH2-5-R-6-R1-C6H2C(O)(R2) (R = H, Cl, Me, Ph, etc.; R1 = H; RR1 = -CH=CH-CH=CH-; R2 = H, Me, Ph, 2-chlorophenyl, etc.) and mono- or dicarbonyl synthons such as acetylacetone, cyclohexanone, 1,2-diphenylethan-1-one, etc. and uses reusable Nafion NR 50 material as a solid catalyst in ethanol under microwave irradiation The protocol has a high generality of functional groups and provides the desired quinolines e.g., I in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction anal.

Synthesis published new progress about Aromatic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Formula: C11H12O3.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Rysak, Vincent; Dixit, Ruchi; Trivelli, Xavier; Merle, Nicolas; Agbossou-Niedercorn, Francine; Vanka, Kumar; Michon, Christophe published the artcile< Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt>, Safety of Ethyl 3-oxo-3-phenylpropanoate, the main research area is ether preparation; ester catalytic reductive deoxygenation.

The catalytic and transition metal-free reductive deoxygenation of esters to ethers through the use of a hydrosilane and a fluorinated borate BArF salt as a catalyst was reported. Exptl. and theor. studies supported the role of noncovalent interactions between the fluorinated catalyst, the hydrosilane and the ester substrate in the reaction mechanism.

Catalysis Science & Technology published new progress about Deoxidation (reductive). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Safety of Ethyl 3-oxo-3-phenylpropanoate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Patel, Ashvani Kumar; Rathor, Shikha Singh; Samanta, Sampak published the artcile< Regioselective access to di- and trisubstituted pyridines via a metal-oxidant-solvent-free domino reaction involving 3-chloropropiophenones>, Electric Literature of 94-02-0, the main research area is heterocyclic pyridine preparation regioselective chemoselective green chem; chloropropiophenone ketone tandem reaction.

A remarkable metal-oxidant-solvent- and base-free domino route for regioselective access to a wide range of 2,4-di- and 2,3,4/6-trisubstituted pyridines, e.g., I including carbo- and heterocyclic fused pyridines is reported. This [3C + 2C + 1N] cyclization reaction occurs between 3-chloropropiophenones RC(O)(CH2)2Cl (R = Ph, 4-iodophenyl, 5-methylthiophen-2-yl, etc.) (3C units), enolizable acyclic/cyclic ketones, e.g., 1,2,3,4-tetrahydronaphthalen-1-one (2C sources) and NH4OAc as a robust N source under neat conditions under an open atm., producing new C=C and C=N-C bonds in highly chemo- and regioselective manners. Interestingly, this eco-friendly method has many pos. features: excellent functional group tolerance, broad substrate scope, good to excellent regioselectivities, promising yields, no-unwanted products, neutral reaction conditions and appropriateness for large-scale synthesis. Mechanism studies reveal that the in situ generated 灏?amino ketone from 3-chloropropiophenone and an ammonium salt undergoes C=N bond formation with a ketone followed by an intramol. cyclization process (C=C bond), which are the decisive steps for pyridine synthesis.

Organic & Biomolecular Chemistry published new progress about C-C bond formation (cn). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Electric Literature of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Djurovic, Alexandre; Vayer, Marie; Li, Zhilong; Guillot, Regis; Baltaze, Jean-Pierre; Gandon, Vincent; Bour, Christophe published the artcile< Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation>, SDS of cas: 94-02-0, the main research area is medium sized carbocycle preparation; alkenyl ketone preparation tandem metathesis transfer hydrogenation.

The first examples of a catalytic tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation are described. 1,4-Cyclohexadiene has been used as an H2 surrogate to reduce the cyclic alkenes formed after the metathesis step. The same cationic gallium(III) complex, [IPr璺疓aCl2][SbF6], performs the two steps with functional group tolerance. This stereoselective reaction leads to 1,2-cis-disubstituted cyclopentanes and various cyclohexanes. DFT computations support an unexpected mechanism involving activation of 1,4-cyclohexadiene by superelectrophilic gallium(III) dimers.

Organic Letters published new progress about Diastereoselective synthesis. 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, SDS of cas: 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Goswami, Prithwish; Cho, Sung Yeon; Park, Jin Hyun; Kim, Woo Hee; Kim, Hyun Jin; Shin, Myoung Hyeon; Bae, Han Yong published the artcile< Efficient access to general 浼?tertiary amines via water-accelerated organocatalytic multicomponent allylation>, Related Products of 94-02-0, the main research area is tertiary amine preparation; ketone allyl boronic acid ester benzhydrazide multicomponent allylation organocatalyst; ketoester allyl boronic acid ester benzhydrazide multicomponent allylation organocatalyst; allyl boronic acid ester ketoester amine multicomponent allylation organocatalyst.

A tetrasubstituted carbon atom connected by three sp3 or sp2-carbons with single nitrogen, i.e., the 浼?tertiary amines I [R = n-Pr, CH2CO2Et, Ph, etc.; R1 = Me, Et, n-Pr, etc.], was an essential structure of diverse naturally occurring alkaloids and pharmaceuticals. The synthetic approach toward ATA structures was intricate, therefore, a straightforward catalytic method had remained a substantial challenge. Herein, an efficient water-accelerated organocatalytic allylation to directly access ATA incorporating homoallylic amine structures I by exploiting readily accessible general ketones/keto esters as useful starting material along with allyl boronic acid esters and benzhydrazide/amines. The synergistic action of a hydrophobic Bronsted acid in combination with a squaramide hydrogen-bonding donor under aqueous condition enabled the facile formation of the desired moiety I. The developed exceptionally mild but powerful system facilitated a broad substrate scope and enabled efficient multi-gram scalability.

Nature Communications published new progress about Allylation. 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Related Products of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Feng, Sitian; Tang, Yitian; Yang, Chenjue; Shen, Chaoren; Dong, Kaiwu published the artcile< Synthesis of Enantioenriched 浼?浼?Difluoro-灏?arylbutanoic Esters by Pd-Catalyzed Asymmetric Hydrogenation>, Related Products of 94-02-0, the main research area is aryldifluorobutanoate enantioselective preparation; palladium catalyst enantioselective hydrogenation aryldifluorobutenoate.

Synthesis of optically active gem-difluorinated organic mols. attracts a great deal of interest due to their unique properties in pharmaceutical and agrochem. areas. Herein, a series of enantioenriched 浼?浼?difluoro-灏?arylbutanoic esters such as (S)-(-)-4-PhC6H4CHMeCF2CO2Et were prepared in high yields (83-99%) with moderate to excellent enantioselectivities (閳?7:3 er) by palladium-catalyzed asym. hydrogenation.

Organic Letters published new progress about Enantioselective synthesis. 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Related Products of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Huang, Zhiliang; Guan, Renpeng; Shanmugam, Muralidharan; Bennett, Elliot L.; Robertson, Craig M.; Brookfield, Adam; McInnes, Eric J. L.; Xiao, Jianliang published the artcile< Oxidative Cleavage of Alkenes by O2 with a Non-Heme Manganese Catalyst>, Safety of Ethyl 3-oxo-3-phenylpropanoate, the main research area is alkene oxygen light manganese oxidation catalyst; ketone preparation.

The oxidative cleavage of C=C double bonds with mol. oxygen to produce carbonyl compounds is an important transformation in chem. and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C=C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atm. pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asym., mixed-valent bis(�oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Journal of the American Chemical Society published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Safety of Ethyl 3-oxo-3-phenylpropanoate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Vereshchagin, Anatoly N.; Iliyasov, Taygib M.; Karpenko, Kirill A.; Smirnov, Vladimir A.; Ushakov, Ivan E.; Elinson, Michail N. published the artcile< Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines>, Electric Literature of 94-02-0, the main research area is tetrahydropyridine preparation diastereoselective; benzylidenemalononitrile oxocarboxylic acid aromatic aldehyde multicomponent heterocyclization ammonium acetate.

A novel four-component diastereoselective synthesis of polysubstituted tetrahydropyridines (4SR,6RS)-I (R = H, 3-F, 4-Me, 4-Cl, etc.; R1 = Me, Et, Ph, 4-bromophenyl; R2 = Me, Et) is reported. The Michael addition – Mannich reaction – cyclization – dehydration cascade of benzylidenemalononitriles RC6H4CH=C(CN)2, esters of 3-oxocarboxylic acids R1C(O)CH2C(O)OR2, aromatic aldehydes RC6H4CHO, and ammonium acetate in methanol provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine- 3-carboxylates (4SR,6RS)-I with two stereocenters in 66-92% yields. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays dual role acting as a base and as a nitrogen source. The formation of single diastereomer was confirmed by singe crystal X-ray diffraction studies.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Electric Literature of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics