Tag: M.W=150-200

Sefkow, Michael; Koch, Andreas; Kleinpeter, Erich published the artcile< New results on the stereoselective alkylations of malic acid derivatives supported by molecular modeling>, Application In Synthesis of 617-55-0, the main research area is stereoselective alkylation malic acid derivative mol modeling.

The stereoselectivity of the alkylation of dialkyl malates is dependent on steric hindrance of both ester alkyl groups. It was found that the two alkyl groups have opposite effects on diastereoselectivity. Increased steric hindrance at the C(1) carboxy group increases the anti-selectivity, whereas increased steric hindrance at the C(4) carboxy group decreases it. The results are explained by comparing the structures of the enolates, which were obtained by mol. modeling. Alkylation at C(4′) of dioxolanones, derived from benzyl-substituted malic acids, with an addnl. stereogenic center on the side chain is dependent on the stereogenic centers of the ring acetal and of the side chain. Alkylation at low temperatures occurs only with cis-dioxolanones having an (R)-configured side-chain stereogenic center. The corresponding trans-dioxolanone and the cis-dioxolanone with a (S)-configured side-chain stereogenic center were recovered unchanged. A rationale is presented with models of monolithiated dioxolanones obtained by ab initio calculations

Helvetica Chimica Acta published new progress about Acetals, cyclic Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent) (of malic acid derivatives). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.

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

Palmer, Francine N.; Lach, Franck; Poriel, Cyril; Pepper, Adrian G.; Bagley, Mark C.; Slawin, Alexandra M. Z.; Moody, Christopher J. published the artcile< The diazo route to diazonamide A: studies on the tyrosine-derived fragment>, Application of C9H9NO4, the main research area is diazonamide tyrosine derived fragment preparation.

Various approaches to the tyrosine-derived fragment of the marine secondary metabolite diazonamide A are described. Initial efforts were focused on the originally proposed structure of the natural product, and a feasibility study established that a model 4-aryltryptamine could be readily prepared For example, Boc-protected 4-bromotryptamine underwent Pd(0)-catalyzed coupling with 3-allyl-2-methoxyphenylboronic acid, derived from 2-bromophenyl allyl ether by Claisen rearrangement, O-methylation and lithiation-boration. The resulting biaryl compound I was elaborated into an 浼?diazo-灏?ketoester II, whose Rh2(OAc)4-catalyzed reaction with Cbz-Val-NH2 gave the desired tryptamine-oxazole III following cyclodehydration of the intermediate ketoamide. Another strategy used Cbz-Tyr-OBu-t to synthesize, in eight steps, tyrosyl benzofuran derivative IV, a potential precursor to the benzofuran ring of the original structure of diazonamide A. Iodination, O-protection and Stille coupling were the key steps in the synthesis of IV.

Organic & Biomolecular Chemistry published new progress about Borylation (coupled with lithiation). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Application of C9H9NO4.

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

Lu, Guan-Han; Huang, Tzu-Chia; Hsueh, Hsiao-Chin; Yang, Shin-Cherng; Cho, Ting-Wei; Chou, Ho-Hsuan published the artcile< Novel N-transfer reagent for converting 浼?amino acid derivatives to 浼?diazo compounds>, Related Products of 30095-98-8, the main research area is diazo dipeptide synthesis isotope thermal decomposition; amino acid nitrogen transfer reagent reaction mechanism.

A novel universal N-transfer reagent for direct and effective transformation of 浼?amino ketones, acetamides, and esters to the corresponding 浼?diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of 浼?substituted-浼?diazo carbonyl compounds from 浼?amino acid derivatives but also permits preparation of 浼?diazo dipeptides from N-terminal dipeptides (32 examples, up to 91%).

Chemical Communications (Cambridge, United Kingdom) published new progress about Amino acids Role: RCT (Reactant), RACT (Reactant or Reagent). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Related Products of 30095-98-8.

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

Pan, Fei; Wu, Bin; Shi, Zhang-Jie published the artcile< Cu-Catalyzed Intramolecular Amidation of Unactivated C(sp3)-H Bonds To Synthesize N-Substituted Indolines>, Application In Synthesis of 30095-98-8, the main research area is indoline preparation intramol amidation unactivated aniline bond; C鈭扝 activation; copper; indoline; radical; synthetic methods.

A copper-catalyzed intramol. amidation of unactivated C(sp3)-H bonds to construct indoline derivatives has been developed. Such an amidation proceeded well at primary C-H bonds preferred to secondary C-H bonds. The transformation owned a broad substrate scope. The corresponding indolines were obtained in good to excellent yields. N-Formal and other carbonyl groups were suitable and were easily deprotected and transformed into Me or long-chained alkyl groups. Preliminary mechanistic studies suggested a radical pathway.

Chemistry – A European Journal published new progress about Amidation (Intramol.). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Application In Synthesis of 30095-98-8.

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

Eckermann, Ruben; Breunig, Michael; Gaich, Tanja published the artcile< Formal Total Synthesis of (�-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements>, Recommanded Product: Methyl 2-(2-nitrophenyl)acetate, the main research area is strictamine formal total synthesis sigmatropic Stevens rearrangement; Stevens rearrangement; [2,3]-sigmatropic rearrangement; alkaloids; diazo compounds; total synthesis.

To date, more than 100 congeners of the akuammiline alkaloid family have been isolated. Their signature structural element is a methanoquinolizidine moiety, a cage-like scaffold structurally related to adamantane. The structural variations of the family members originate from oxidative processes that mostly trigger rearrangements of the methanoquinolizidine motif. The family of the akuammiline alkaloids is best represented by strictamine. It bears the least functionalized carbon skeleton of all family members without lacking the signature structural motifs. Herein, we report the formal synthesis of (�-strictamine (I) through a Stevens [2,3]-sigmatropic rearrangement as a key step and the synthetic pitfalls related with its synthesis.

Chemistry – A European Journal published new progress about [2,3]-Sigmatropic rearrangement. 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Recommanded Product: Methyl 2-(2-nitrophenyl)acetate.

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

Carry, Jean-Christophe; Clerc, Francois; Minoux, Herve; Schio, Laurent; Mauger, Jacques; Nair, Anil; Parmantier, Eric; Le Moigne, Ronan; Delorme, Cecile; Nicolas, Jean-Paul; Krick, Alain; Abecassis, Pierre-Yves; Crocq-Stuerga, Veronique; Pouzieux, Stephanie; Delarbre, Laure; Maignan, Sebastien; Bertrand, Thomas; Bjergarde, Kirsten; Ma, Nina; Lachaud, Sylvette; Guizani, Houlfa; Lebel, Remi; Doerflinger, Gilles; Monget, Sylvie; Perron, Sebastien; Gasse, Francis; Angouillant-Boniface, Odile; Filoche-Romme, Bruno; Murer, Michel; Gontier, Sylvie; Prevost, Celine; Monteiro, Marie-Line; Combeau, Cecile published the artcile< SAR156497, an Exquisitely Selective Inhibitor of Aurora Kinases>, Related Products of 252932-48-2, the main research area is SAR156497 antitumor Aurora kinase.

The Aurora family of serine/threonine kinases is essential for mitosis. Their crucial role in cell cycle regulation and aberrant expression in a broad range of malignancies have been demonstrated and have prompted intensive search for small mol. Aurora inhibitors. Indeed, over 10 of them have reached the clinic as potential anticancer therapies. We report herein the discovery and optimization of a novel series of tricyclic mols. that has led to SAR156497, an exquisitely selective Aurora A, B, and C inhibitor with in vitro and in vivo efficacy. We also provide insights into its mode of binding to its target proteins, which could explain its selectivity.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 252932-48-2 belongs to class esters-buliding-blocks, and the molecular formula is C7H10N2O2, Related Products of 252932-48-2.

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