609-08-5 Archives - Page 6 of 9 - Esters-buliding-blocks

Chan, Wei Chuen’s team published research in Journal of Organic Chemistry in 2021 | CAS: 609-08-5

Diethyl 2-methylmalonate(cas: 609-08-5) belongs to aliphatic hydrocarbons. Aliphatic hydrocarbons belong to the most abundant fraction in crude oil. Aliphatics molecules are linear or branched open-chain structures such as n-alkanes, isoalkanes, cycloalkanes (naphthenes), terpenes and steranes.Category: esters-buliding-blocks

《Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step》 was written by Chan, Wei Chuen; Vinod, Jincy K.; Koide, Kazunori. Category: esters-buliding-blocks And the article was included in Journal of Organic Chemistry in 2021. The article conveys some information:

We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by exptl. and d. functional theory studies. The experimental part of the paper was very detailed, including the reaction process of Diethyl 2-methylmalonate(cas: 609-08-5Category: esters-buliding-blocks)

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

Scheeff, Stephan’s team published research in Journal of Organic Chemistry in 2021 | CAS: 609-08-5

Scheeff, Stephan; Riviere, Solenne; Ruiz, Johal; Dedenbach, Simon; Menche, Dirk published their research in Journal of Organic Chemistry in 2021. The article was titled 《Modular Total Synthesis of iso-Archazolids and Archazologs》.Reference of Diethyl 2-methylmalonate The article contains the following contents:

Full details on the design, development, and successful implementation of suitable synthetic strategies directed toward the total synthesis of iso-archazolids and archazologs are reported. Both a biomimetic and a multistep total synthesis of iso-archazolid B, the most potent and least abundant archazolid, are described. The bioinspired conversion from archazolid B was realized by a high-yielding 1,8-Diazabicyclo[5.4.0]undec-7-ene catalyzed one-step double-bond shift. A highly stereoselective total synthesis was accomplished in 25 steps, involving a sequence of highly stereoselective aldol reactions, an efficient aldol condensation to forge two elaborate fragments, and a challenging ring-closing metathesis macrocyclization with an unusual Stewart-Grubbs catalyst. These strategies proved to be generally useful and could be successfully implemented for the preparation of three novel iso-archazolids as well as five novel archazologs, lacking the thiazole side chain. A wide variety of further archazolids and archazologs may now be targeted for exploration of the promising anticancer potential of these polyketide macrolides. The experimental part of the paper was very detailed, including the reaction process of Diethyl 2-methylmalonate(cas: 609-08-5Reference of Diethyl 2-methylmalonate)

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

Gomes, Carla M. B.’s team published research in Journal of Chemical Ecology in 2022 | CAS: 609-08-5

Product Details of 609-08-5In 2022 ,《Determination of the Absolute Configuration of the Male-Produced Sex Pheromone of the Stink Bug Pellaea stictica, (2R,4R,8R)-2,4,8,13-Tetramethyltetradecan-1-ol by Stereoselective Synthesis Coupled with Enantiomeric Resolution》 was published in Journal of Chemical Ecology. The article was written by Gomes, Carla M. B.; Souza, Joao P. A.; Millar, Jocelyn G.; Zarbin, Paulo H. G.. The article contains the following contents:

A series of syntheses was designed to: (a) furnish a mixture of all possible stereoisomers; (b) a narrowed down group of diastereomers, and (c) one specific enantiomer. A crucial step in the syntheses involved a coupling reaction between two key intermediates: a phosphonium salt and an aldehyde, through a Wittig olefination. NMR data of a mixture of the synthetic pheromone diastereomers and further comparison of GC retention times with that of the natural product by gas chromatog. suggested that the Me branches at C2 and C4 were in a syn relationship, reducing the possibilities to only four of the eight possible stereoisomers. Employing GC anal., chiral derivatization reagents and synthetic (2R,4R,8R)-2,4,8,13-tetramethyltetradecan-1-ol it was possible to confirm the configuration of the Me branch at C8 as R, reducing the number of possible stereoisomers to two. After enantioselective synthesis of (2R,4R,8R)-2,4,8,13-tetramethyltetradecan-1-ol, the absolute configurations of all Me branches of the natural compound were confirmed as R, fully identifying the male-produced sex pheromone of P. stictica as (2R,4R,8R)-2,4,8,13-tetramethyltetradecan-1-ol. In the experiment, the researchers used many compounds, for example, Diethyl 2-methylmalonate(cas: 609-08-5Product Details of 609-08-5)

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

Hari, Durga Prasad’s team published research in Chemistry – A European Journal in 2019 | CAS: 609-08-5

The author of 《Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds》 were Hari, Durga Prasad; Schouwey, Lionel; Barber, Verity; Scopelliti, Rosario; Fadaei-Tirani, Farzaneh; Waser, Jerome. And the article was published in Chemistry – A European Journal in 2019. Computed Properties of C8H14O4 The author mentioned the following in the article:

The first synthesis was reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle was replaced by a nitrogen atom. The substituent on the nitrogen enabled further fine-tuning of the reagent structure and reactivity. EBZ reagents were obtained easily from the corresponding benzamides by using a one-step procedure and displayed reactivity comparable to that of EBX reagents. In particular, they were applied in an asym. copper-catalyzed oxyalkynylation of diazo compounds, which proceeded in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.Diethyl 2-methylmalonate(cas: 609-08-5Computed Properties of C8H14O4) was used in this study.

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

Butcher, Trevor W.’s team published research in Nature (London, United Kingdom) in 2020 | CAS: 609-08-5

《Desymmetrization of difluoromethylene groups by C-F bond activation》 was published in Nature (London, United Kingdom) in 2020. These research results belong to Butcher, Trevor W.; Yang, Jonathan L.; Amberg, Willi M.; Watkins, Nicholas B.; Wilkinson, Natalie D.; Hartwig, John F.. Application In Synthesis of Diethyl 2-methylmalonate The article mentions the following:

Tertiary stereogenic centers containing one fluorine atom are valuable for medicinal chem. because they mimic common tertiary stereogenic centers containing one hydrogen atom, but they possess distinct charge distribution, lipophilicity, conformation and metabolic stability1-3. Although tertiary stereogenic centers containing one hydrogen atom are often set by enantioselective desymmetrization reactions at one of the two carbon-hydrogen (C-H) bonds of a methylene group, tertiary stereocenters containing fluorine have not yet been constructed by the analogous desymmetrization reaction at one of the two carbon-fluorine (C-F) bonds of a difluoromethylene group3. Fluorine atoms are similar in size to hydrogen atoms but have distinct electronic properties, causing C-F bonds to be exceptionally strong and geminal C-F bonds to strengthen one another4. Thus, exhaustive defluorination typically dominates over the selective replacement of a single C-F bond, hindering the development of the enantioselective substitution of one fluorine atom to form a stereogenic center5,6. Here the authors report the catalytic, enantioselective activation of a single C-F bond in an allylic difluoromethylene group to provide a broad range of products containing a monofluorinated tertiary stereogenic center. By combining a tailored chiral iridium phosphoramidite catalyst, which controls regioselectivity, chemoselectivity and enantioselectivity, with a fluorophilic activator, which assists the oxidative addition of the C-F bond, these reactions occur in high yield and selectivity. The design principles proposed in this work extend to palladium-catalyzed benzylic substitution, demonstrating the generality of the approach. In the experimental materials used by the author, we found Diethyl 2-methylmalonate(cas: 609-08-5Application In Synthesis of Diethyl 2-methylmalonate)

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

Marrazzo, John-Paul R.’s team published research in Journal of Organic Chemistry in 2022 | CAS: 609-08-5

In 2022,Marrazzo, John-Paul R.; Chao, Allen; Li, Yajun; Fleming, Fraser F. published an article in Journal of Organic Chemistry. The title of the article was 《Copper-Catalyzed Conjugate Additions to Isocyanoalkenes》.Recommanded Product: Diethyl 2-methylmalonate The author mentioned the following in the article:

A copper iodide-Pyox complex catalyzed the first conjugate addition of diverse sulfur, nitrogen, and carbon nucleophiles to isocyanoalkenes to gave isocyano(aryl)ethyl(sulfane/alkyl/imidazole/isoindoline-1,3-dione) I [Ar = 2-MeOC6H4, 4-PhC6H4, R = allylsulfanyl, imidazol-1-yl, cyano(diphenyl)methyl, etc.]. The anionic addition generates metalated isocyanoalkanes capable of SNi displacements, provided a rapid route to a series of functionalized, cyclic isocyanoalkanes II [R1 = 2-MeC6H4, 2-MeOC6H4, 4-PhC6H4, etc.; R2 = H, n-Pr, R3 = Me, Et, t-Bu] and III. The Cu(I)I-Pyox complex efficiently catalyzes a first-in-class conjugate addition affording a range of complex, functionalized isocyanoalkanes I, II and III that were otherwise challenging to synthesize while laying a foundation for catalytic reactions that maintain the isocyanide group. In the experimental materials used by the author, we found Diethyl 2-methylmalonate(cas: 609-08-5Recommanded Product: Diethyl 2-methylmalonate)

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

Li, Zhanhui’s team published research in European Journal of Medicinal Chemistry in 2022 | CAS: 609-08-5

Formula: C8H14O4In 2022 ,《Design, synthesis, and evaluation of potent RIPK1 inhibitors with in vivo anti-inflammatory activity》 was published in European Journal of Medicinal Chemistry. The article was written by Li, Zhanhui; Hao, Yongjin; Yang, Chengkui; Yang, Qing; Wu, Shuwei; Ma, Haikuo; Tian, Sheng; Lu, Haohao; Wang, Jingrui; Yang, Tao; He, Sudan; Zhang, Xiaohu. The article contains the following contents:

RIPK1 plays a key role in the necroptosis pathway that regulates inflammatory signaling and cell death in various diseases, including inflammatory and neurodegenerative diseases. Herein, we report a series of potent RIPK1 inhibitors, represented by compound 70. Compound 70 efficiently blocks necroptosis induced by TNFα in both human and mouse cells (EC50 = 17-30 nM). Biophys. assay demonstrates that compound 70 potently binds to RIPK1 (Kd = 9.2 nM), but not RIPK3 (Kd > 10,000 nM). Importantly, compound 70 exhibits greatly improved metabolic stability in human and rat liver microsomes compared to compound 6 (PK68), a RIPK1 inhibitor reported in our previous work. In addition, compound 70 displays high permeability in Caco-2 cells and excellent in vitro safety profiles in hERG and CYP assays. Moreover, pre-treatment of 70 significantly ameliorates hypothermia and lethal shock in SIRS mice model. Lastly, compound 70 possesses favorable pharmacokinetic parameters with moderate clearance and good oral bioavailability in SD rat. Taken together, our work supports 70 as a potent RIPK1 inhibitor and highlights its potential as a prototypical lead for further development in necroptosis-associated inflammatory disorders. The experimental part of the paper was very detailed, including the reaction process of Diethyl 2-methylmalonate(cas: 609-08-5Formula: C8H14O4)

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

Dimitrov, Ivaylo V.’s team published research in Bioorganic & Medicinal Chemistry in 2019 | CAS: 609-08-5

The author of 《Ketamine esters and amides as short-acting anesthetics: structure-activity relationships for the side-chain》 were Dimitrov, Ivaylo V.; Harvey, Martyn G.; Voss, Logan J.; Sleigh, James W.; Bickerdike, Michael J.; Denny, William A.. And the article was published in Bioorganic & Medicinal Chemistry in 2019. Name: Diethyl 2-methylmalonate The author mentioned the following in the article:

N-Aliphatic ester analogs of the non-opioid ketamine (1) retain effective anesthetic/analgesic properties while minimizing ketamine’s psychomimetic side-effects. We show that the anesthetic/analgesic properties of these ester analogs depend critically on the length (from 2 to 4 carbons), polarity and steric cross-section of the aliphatic linker chain. More stable amide and ethylsulfone analogs generally showed weaker anesthetic/analgesic activity. There was no correlation between the anesthetic/analgesic properties of the compounds and their binding affinities for the N-methyl-D-aspartate (NMDA) receptor.Diethyl 2-methylmalonate(cas: 609-08-5Name: Diethyl 2-methylmalonate) was used in this study.

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

Porey, Arka’s team published research in Angewandte Chemie, International Edition in 2021 | CAS: 609-08-5

《Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides》 was written by Porey, Arka; Mondal, Bhaskar Deb; Guin, Joyram. Application In Synthesis of Diethyl 2-methylmalonate And the article was included in Angewandte Chemie, International Edition in 2021. The article conveys some information:

Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chem., material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alc. with a cinnamaldehyde in the presence of an N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.Diethyl 2-methylmalonate(cas: 609-08-5Application In Synthesis of Diethyl 2-methylmalonate) was used in this study.

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

Chen, Yixuan’s team published research in Angewandte Chemie, International Edition in 2022 | CAS: 609-08-5

《Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand》 was written by Chen, Yixuan; Gu, Yuefei; Meng, Huan; Shao, Qianzhen; Xu, Zhenchuang; Bao, Wenjing; Gu, Yucheng; Xue, Xiao-Song; Zhao, Yanchuan. SDS of cas: 609-08-5This research focused onunsym iodonium salt preparation; Cross-Coupling; C−H Functionalization; Diaryliodonium Salts; Hypervalent Compounds; Structural Diversification. The article conveys some information:

A two-step strategy for the transition-metal-free C-H functionalization of arenes using unsym. iodonium salts as versatile synthetic linchpins was presented. The key to the success of this strategy was the identification of the 3,5-dimethyl-4-isoxazolyl (DMIX) group as a superior dummy ligand, which enabled not only site-selective C-H functionalization to afford unsym. iodonium salts I [R = Ph, 2-thienyl, 3,4-di-ClC6H4, etc.; X = OAc, OTs], but also highly selective aryl transfer during the subsequent metal-free coupling reaction. Both electron-rich and moderately electron-deficient arenes could be converted into the iodonium salts through C-H functionalization, allowing for diverse structural elaboration by metal-free C-N, C-C, C-S, and C-O coupling.Diethyl 2-methylmalonate(cas: 609-08-5SDS of cas: 609-08-5) was used in this study.

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