Tag: M.W=100-150

Calow, Adam D. J. published the artcileCarbonylative N-Heterocyclization via Nitrogen-Directed C-C Bond Activation of Nonactivated Cyclopropanes, Application of Dimethyl fumarate, the publication is Journal of the American Chemical Society (2022), 144(25), 11069-11074, database is CAplus and MEDLINE.

Under Rh-catalyzed conditions, secondary amines and anilines function as directing groups to facilitate regioselective C-C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles underwent carbonylative C-N bond formation en route to challenging seven- and eight-membered lactams. The processes represented rare examples where C-C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design.

Journal of the American Chemical Society published new progress about 624-49-7. 624-49-7 belongs to esters-buliding-blocks, auxiliary class Inhibitor,Natural product, name is Dimethyl fumarate, and the molecular formula is C6H8O4, Application of Dimethyl fumarate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Shershnev, Ivan published the artcileThe use of α-diazo-γ-butyrolactone in the Buchner-Curtius-Schlotterbeck reaction of cyclic ketones: A facile entry into spirocyclic scaffolds, Related Products of esters-buliding-blocks, the publication is Tetrahedron Letters (2019), 60(27), 1800-1802, database is CAplus.

The first example of the Buchner-Curtius-Schlotterbeck reaction of cyclic ketones with a stabilized cyclic diazo compound partner is described. The approach towards spirocyclic scaffolds has been exemplified with readily available α-diazo-γ-butyrolactone. The reaction proved to be viable with BF₃·OEt₂ as the preferred catalyst and displayed substantial sensitivity to the size of the cyclic ketone.

Tetrahedron Letters published new progress about 517-23-7. 517-23-7 belongs to esters-buliding-blocks, auxiliary class Tetrahydrofuran,Ketone,Ester, name is 3-Acetyldihydrofuran-2(3H)-one, and the molecular formula is C5H6BNO2, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sauerland, Max B. published the artcileElectrophile versus oxidant modification of cysteine residues: Kinetics as a key driver of protein modification, Application of Dimethyl fumarate, the publication is Archives of Biochemistry and Biophysics (2022), 109344, database is CAplus and MEDLINE.

A review. Humans have widespread exposure to both oxidants, and soft electrophilic compounds such as alpha,beta-unsaturated aldehydes and quinones. Electrophilic motifs are commonly found in a drugs, industrial chems., pollutants and are also generated via oxidant-mediated degradation of biomols. including lipids (e.g. formation of 4-hydroxynonenal, 4-hydroxyhexenal, prostaglandin J2). All of these classes of compounds react efficiently with Cys residues, and the particularly the thiolate anion, with this resulting in Cys modification via either oxidation or adduct formation. This can result in deleterious or beneficial effects, that are either reversible (e.g. in cell signalling) or irreversible (damaging). For example, acrolein is a well-established toxin, whereas dimethylfumarate is used in the treatment of multiple sclerosis and psoriasis. This short review discusses the targets of alpha,beta-unsaturated aldehydes, and particularly two prototypic cases, acrolein and dimethylfumarate, and the factors that control the selectivity and kinetics of reaction of these species. Comparison is made between the reactivity of oxidants vs. soft electrophiles. These rate constants indicate that electrophiles can be significant thiol modifying agents in some situations, as they have rate constants similar to or greater than species such as H2O2, can be present at higher concentrations, and are less efficiently removed by protective systems when compared to H2O2. They may also induce similar or higher levels of modification than highly reactive oxidants, due to the very low concentrations of oxidants formed in most in vivo situations.

Archives of Biochemistry and Biophysics published new progress about 624-49-7. 624-49-7 belongs to esters-buliding-blocks, auxiliary class Inhibitor,Natural product, name is Dimethyl fumarate, and the molecular formula is C6H8O4, Application of Dimethyl fumarate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhu, Jing published the artcileRadical Hydrosilylation of Alkynes Catalyzed by Eosin Y and Thiol under Visible Light Irradiation, Product Details of C5H10O2S, the publication is Organic Letters (2018), 20(11), 3174-3178, database is CAplus and MEDLINE.

A visible light-promoted hydrosilylation of alkynes was explored and achieved using 1 mol % organic dye Eosin Y as the photocatalyst and a catalytic amount of thiol as the radical quencher. The corresponding alkenylsilanes were provided with high regio- and stereoselectivites in the reactions of various terminal and internal alkynes. The reaction is preferentially initiated by a single electron transfer process, and a photoredox pathway is suggested.

Organic Letters published new progress about 19788-49-9. 19788-49-9 belongs to esters-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Ester, name is Ethyl 2-mercaptopropanoate, and the molecular formula is C17H14F3N3O2S, Product Details of C5H10O2S.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Stack, Jeffrey G. published the artcileA new chiral auxiliary for asymmetric thermal reactions: high stereocontrol in radical addition, allylation, and annulation reactions, Formula: C8H16O2, the publication is Journal of the American Chemical Society (1992), 114(18), 7007-18, database is CAplus.

A new imide chiral auxiliary, endo-7-(2-benzoxazolyl)-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one (I), is prepared from Kemp’s triacid and resolved via its menthyl carbamate. Mixed fumarate derivatives of the auxiliary show unprecedented control of regiochem. and β-stereochem. in representative radical addition reactions. Chiral radicals derived from I also show extremely high levels of stereoselectivity in representative radical allylation and cyclization reactions. Structural features of the chiral auxiliary and features of radical addition are integrated into a model for stereoselection.

Journal of the American Chemical Society published new progress about 5340-78-3. 5340-78-3 belongs to esters-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethyltert-butylacetate, and the molecular formula is C18H28N2O7, Formula: C8H16O2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Kieslich, David published the artcileFormation of δ-Lactones by Cyanide Catalyzed Rearrangement of α-Hydroxy-β-oxoesters, Related Products of esters-buliding-blocks, the publication is Organic Letters (2021), 23(3), 953-957, database is CAplus and MEDLINE.

δ-Valerolactone derivatives such as I are formed by cyanide-catalyzed ring-transformation of cyclic α-hydroxy-β-oxoesters such as II (R = HO). This unprecedented reaction defines a new synthetic methodol., and the products are obtained in up to quant. yields. Several alkyl substitutions as well as different ester residues are tolerated. Furthermore, benzo- and heteroarene-annulated starting materials such as II (R = HO) are converted without difficulty. As an addnl. benefit, the starting materials are straightforwardly accessed by cerium-catalyzed aerobic α-hydroxylation of readily available β-oxoesters such as II (R = H).

Organic Letters published new progress about 517-23-7. 517-23-7 belongs to esters-buliding-blocks, auxiliary class Tetrahydrofuran,Ketone,Ester, name is 3-Acetyldihydrofuran-2(3H)-one, and the molecular formula is C6H8O3, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Lang, S. A. Jr. published the artcileβ-Aminocinnamonitriles as potential antiinflammatory agents, Category: esters-buliding-blocks, the publication is Journal of Medicinal Chemistry (1975), 18(4), 441-3, database is CAplus and MEDLINE.

Of 13 title compounds, prepared by the reaction of salts of acetonitrile [75-05-8] and propionitrile [107-12-0] with the appropriate arylnitrile, only the parent β-aminocinnamonitrile [1823-99-0] had activity comparable to aspirin [50-78-2] in the carrageenan-induced rat paw edema test. Of 7 aminoarylacrylonitriles, prepared by the reaction of arylcyanoacetaldehydes with formamide derivatives, and 5 phenylpropiolate derivatives, none showed antiinflammatory activity.

Journal of Medicinal Chemistry published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Wang, Da-Wei published the artcileDiscovery of N-Phenylaminomethylthioacetylpyrimidine-2,4-diones as Protoporphyrinogen IX Oxidase Inhibitors through a Reaction Intermediate Derivation Approach, Recommanded Product: Ethyl 2-mercaptopropanoate, the publication is Journal of Agricultural and Food Chemistry (2021), 69(14), 4081-4092, database is CAplus and MEDLINE.

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is an effective target for green herbicide discovery. In this work, we reported the unexpected discovery of a novel series of N-phenylaminomethylthioacetylpyrimidine-2,4-diones (2-6) as promising PPO inhibitors based on investigating the reaction intermediates of our initially designed N-phenyluracil thiazolidinone (1). An efficient one-pot procedure that gave 41 target compounds in good to high yields was developed. Systematic Nicotiana tabacum PPO (NtPPO) inhibitory and herbicidal activity evaluations led to identifying some compounds with improved NtPPO inhibition potency than saflufenacil and good post-emergence herbicidal activity at 37.5-150 g of ai/ha. Among these analogs, Et 2-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)amino)methyl)thio)acetate (2c) (K_i = 11 nM), exhibited excellent weed control at 37.5-150 g of ai/ha and was safe for rice at 150 g of ai/ha, indicating that compound 2c has the potential to be developed as a new herbicide for weed management in paddy fields. Addnl., our mol. simulation and metabolism studies showed that the side chains of compound 2c could form a hydrogen-bond-mediated seven-membered ring system; substituting a Me group at R¹ could reinforce the hydrogen bond of the ring system and reduce the metabolic rate of target compounds in planta.

Journal of Agricultural and Food Chemistry published new progress about 19788-49-9. 19788-49-9 belongs to esters-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Ester, name is Ethyl 2-mercaptopropanoate, and the molecular formula is C9H21NO3, Recommanded Product: Ethyl 2-mercaptopropanoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Xiong, Mingteng published the artcileSynthesis of Polysubstituted Pyrroles through Electro-Oxidative Annulation of 1,3-Dicarbonyl Compounds and Primary Amines, Synthetic Route of 30414-53-0, the publication is Journal of Organic Chemistry (2021), 86(7), 4986-4993, database is CAplus and MEDLINE.

Synthetic method of polysubstituted pyrroles I [R¹ = H, 2-Me, 2-MeO, etc.; R² = Me, Et; R³ = Me, Et, i-Pr] from easily available materials, 1,3-dicarbonyl compounds and primary amines, via electro-oxidative intermol. annulation was reported. Under similar conditions, enamines were also converted smoothly into desired products I, indicating that in situ formed enamines were crucial intermediates for the first transformation. Neither transition-metal salts nor harsh conditions were required to facilitate the dehydrocyclization process.

Journal of Organic Chemistry published new progress about 30414-53-0. 30414-53-0 belongs to esters-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Ketone,Ester, name is Methyl 3-oxovalerate, and the molecular formula is C10H10O2, Synthetic Route of 30414-53-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Chen, Qian published the artcileSynthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride, Recommanded Product: Ethyl 3-(dimethylamino)acrylate, the publication is Nongyao (2012), 51(8), 569-572, database is CAplus.

This article aims to optimize a reasonable route of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride on industrial scale. 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride was synthesized from Et 3-(dimethylamino)arylate via four steps including acylation, cyclization, hydrolysis, chlorination. The total yield was 46.8%, and the purity of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid was 96.1% (HPLC). The products and intermediates were determined by ¹H NMR or MS and so on. The yield is improved and the operation process is simple, which is suitable for industrial production

Nongyao published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Recommanded Product: Ethyl 3-(dimethylamino)acrylate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics