Tag: M.W=100-150

Patel, Harshkumar H. published the artcileFormation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers, Safety of 3-Acetyldihydrofuran-2(3H)-one, the publication is Journal of the American Chemical Society (2018), 140(18), 5895-5898, database is CAplus and MEDLINE.

This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantioselective and site-selective coupling with acyclic aryl enol ethers in the presence of a chiral palladium catalyst. This transform provides chiral allylic ether products in high yields and excellent enantiomeric ratios, furnishing a unique disconnection to incorporate heteroatoms at a stereocenter. Finally, the applicability of the products to target synthesis was demonstrated through the formation of a chiral allylic alc. and the generation of a flavone-inspired product.

Journal of the American Chemical Society 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, Safety of 3-Acetyldihydrofuran-2(3H)-one.

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

Yuan, Qianjia published the artcileEnantioselective Synthesis of γ-Functionalized Cyclopentenones and β-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy, Quality Control of 517-23-7, the publication is Advanced Synthesis & Catalysis (2020), 362(2), 326-330, database is CAplus and MEDLINE.

In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives was described. This method granted facile access to diverse γ-functionalized cyclopentenones I [Ar = Ph, 2-naphthyl, benzo[d][1,3]dioxol-5-yl, 4-oxocyclopent-2-en-1-yl, etc.] and δ-functionalized cycloheptenones II [R = Ph, 4-CF₃C₆H₄, C(Me):C(Me)CO₂Et, etc.]. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity.

Advanced Synthesis & Catalysis 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 C39H35N5O8, Quality Control of 517-23-7.

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

Chahal, Mandeep K. published the artcileMolecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis, Formula: C6H10O3, the publication is European Journal of Organic Chemistry (2020), 2020(1), 82-90, database is CAplus.

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramol. hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a mol. engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions (e.g., catalyst I). Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.

European 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 C6H10O3, Formula: C6H10O3.

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

Yu, Bao published the artcileSilver(I) Oxide-/DBU-Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation, Recommanded Product: 3-Acetyldihydrofuran-2(3H)-one, the publication is Chemistry – A European Journal (2020), 26(72), 17455-17461, database is CAplus and MEDLINE.

Herein, a formal [3+2] cyclization mediated by silver(I) oxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was described. Through a broad variety of carbonyl compounds, this system can promote cyclization reactions with high yield (up to 85%) and diastereoselectivity (up to 95:5) for a straightforward access to complex and congested dihydrofuran derivatives in one step under mild conditions. Based on DFT studies, the proposed mechanism would involve an allenyl silver intermediate.

Chemistry – A European Journal 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 C4Br2N2O4S, Recommanded Product: 3-Acetyldihydrofuran-2(3H)-one.

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

Markovic, Rade published the artcileAn expedient solvent-free synthesis of (Z)-2-alkylidene-4-oxothiazolidine derivatives under microwave irradiation, COA of Formula: C5H10O2S, the publication is ARKIVOC (Gainesville, FL, United States) (2006), 83-90, database is CAplus.

A new and efficient microwave-assisted synthesis of (Z)-2-alkylidene-4-oxothiazolidines under solvent-free conditions and without solid support, is described. In comparison to conventional technique, exptl. evidence reveals the benefits of the MW-promoted synthesis of functionalized 4-oxothiazolidine derivatives in terms of simple workup, efficiency, and safe reproducibility. The method, as environmentally cleaner, was shown to be potentially applicable to similar chem. processes, such as the preparation of not easily obtainable 4-oxo-1,3-thiazinan-2-ylidenes.

ARKIVOC (Gainesville, FL, United States) 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 C5H10O2S, COA of Formula: C5H10O2S.

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

Zhang, Lei published the artcileOxidase-Type C-H/C-H Coupling Using an Isoquinoline-Derived Organic Photocatalyst, Product Details of C6H8O4, the publication is Angewandte Chemie, International Edition (2022), 61(20), e202202649, database is CAplus and MEDLINE.

Herein, an isoquinoline-derived diaryl ketone-type photocatalyst I, which has much enhanced absorption of blue and visible light compared to conventional diaryl ketones was reported. This photocatalyst enables dehydrogenative cross-coupling of heteroarenes e.g., II with inactivated and activated alkanes viz. cyclohexane, THF, adamantane, etc. as well as aldehydes viz. propanal, pentanal, 3-methylbutanal, cyclopropanecarbaldehyde, cyclopentanecarbaldehyde using air as the oxidant. A wide range of heterocycles with various functional groups are suitable substrates. Transient absorption and excited-state quenching experiments point to an unconventional mechanism that involves an excited state ”self-quenching” process to generate the N-radical cation form of the sensitizer, which subsequently abstracts a hydrogen atom from the alkane substrate to yield a reactive alkyl radical.

Angewandte Chemie, International Edition 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 C10H6F17N, Product Details of C6H8O4.

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

Huang, Sijia published the artcileChemical recycling of poly(thiourethane) thermosets enabled by dynamic thiourethane bonds, Category: esters-buliding-blocks, the publication is Polymer Chemistry (2020), 11(43), 6879-6883, database is CAplus.

Recycling of polyurethanes is largely infeasible due to the harsh reprocessing conditions and associated risks of side reactions and degradation whereas polymer networks incorporating dynamic covalent bonds represent an attractive approach to the design of recyclable materials. Here, we report findings on the dynamic nature of thiourethanes, and their application as a new class of recyclable analogs of urethane materials. A series of small mol. experiments was initially conducted to determine the equilibrium constant and exchange reaction kinetic constant for the thiol-isocyanate reaction. Furthermore, incorporating those thiourethane moieties into a cross-linked network resulted in thermoset materials that are readily depolymerized to liquid oligomers. The resultant oligomers can be re-crosslinked to thiourethanes without any loss of performance nor change in mech. properties (peak stress of 25 MPa with max strain of 200%). Moreover, the recycled thiol oligomers from thiourethane network polymers could potentially be transformed into other materials with mech. properties that exceed those of the initial, pristine thiourethane materials. Overall, the ease with which these polythiourethanes are polymerized, recycled and reformulated gives a new direction and hope in the design of sustainable polymers.

Polymer 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 C5H10O2S, Category: esters-buliding-blocks.

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

Netz, Astrid published the artcileFacial diastereoselectivity in cationic propargylations with planar-chiral areneCr(CO)₃-substituted propargyl cations, Application In Synthesis of 924-99-2, the publication is European Journal of Organic Chemistry (2005), 1823-1833, database is CAplus.

The planar-chiral (o-methoxyphenyl)chromium tricarbonyl-substituted propargyl cation reacts with silyl enol ether derivatives with poor and with enamines with good facial diastereoselectivity to give rise to the (arene)carbonylchromium-substituted propargylated cyclohexan-2-ones, and carboxylic acid, γ-lactone, cyclopentan-2-one, and esters. Structural correlations were unambiguously deduced from x-ray structure. The origin of facial diastereoselectivity with this class of organometallic electrophiles lies in steric and stereoelectronic biases rather than in purely electronic nucleophilicity.

European Journal of Organic 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, Application In Synthesis of 924-99-2.

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

Sokolov, Alexey S. published the artcileGeneration of Cyclopentadiene for Diels-Alder Reactions by Visible-Light Irradiation of Iron Sandwich Complexes, Synthetic Route of 624-49-7, the publication is Helvetica Chimica Acta (2022), 105(4), e202100246, database is CAplus.

Cyclopentadienes readily undergo fast and selective Diels-Alder reactions which can be used for conjugation of biomols. and polymers. Herein authors present a new method for the photochem. generation of cyclopentadienes by the visible light irradiation of the iron complexes [(C₅H₄R)Fe(arene)]+. This reaction proceeds at room temperature, in water, and in the presence of potentially interfering amino acids. Free cyclopentadiene is trapped by dienophiles to give the corresponding Diels-Alder adducts in 72-95% yield.

Helvetica Chimica Acta 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 C22H12F6O6S2, Synthetic Route of 624-49-7.

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

Naumov, Pance published the artcileStructure and Spectroscopy of Oxyluciferin, the Light Emitter of the Firefly Bioluminescence, Application In Synthesis of 19788-49-9, the publication is Journal of the American Chemical Society (2009), 131(32), 11590-11605, database is CAplus and MEDLINE.

The crystal structures of the pure, unsubstituted firefly emitter oxyluciferin (OxyLH₂) and its 5-Me analog (MOxyLH₂) were determined for the first time to reveal that both mols. exist as pure trans-enol forms, enol-OxyLH₂ and enol-MOxyLH₂, assembled as head-to-tail hydrogen-bonded dimers. Their steady-state absorption and emission spectra (in solution and in the solid state) and nanosecond time-resolved fluorescence decays (in solution) were recorded and assigned to the six possible trans chem. forms of the emitter and its anions. The spectra of the pure emitter were compared to its bioluminescence and fluorescence spectra when it is complexed with luciferase from the Japanese firefly (Luciola cruciata) and interpreted in terms of the intermol. interactions based on the structure of the emitter in the luciferase active site. The wavelengths of the emission spectral maxima of the six chem. forms of OxyLH₂ are generally in good agreement with the theor. predicted energies of the S-S₁ transitions and range from the blue to the red regions, while the resp. absorption maxima range from the UV to the green regions. It was confirmed that both neutral forms, phenol-enol and phenol-keto, are blue emitters, whereas the phenolate-enol form is yellow-green emitter. The phenol-enolate form, which probably only exists as a mixture with other species, and the phenolate-enolate dianion are yellow or orange emitters with close position of their emission bands. The phenolate-keto form always emits in the red region. The concentration ratio of the different chem. species in solutions of OxyLH₂ is determined by several factors which affect the intricate triple chem. equilibrium, most notably the pH, solvent polarity, hydrogen bonding, presence of addnl. ions, and π-π stacking. Due to the stabilization of the enol group of the 4-hydroxythiazole ring by hydrogen bonding to the proximate adenosine monophosphate, which according to the d. functional calculations is similar to that due to the dimerization of two enol mols. observed in the crystal, the phenolate ion of the enol tautomer, which is the predominant ground-state species within the narrow pH interval 7.44-8.14 in buffered aqueous solutions, is the most probable emitter of the yellow-green bioluminescence common for most wild-type luciferases. This conclusion is supported by the bioluminescence/fluorescence spectra and the NMR data, as well the crystal structures of OxyLH₂ and MOxyLH₂, where the conjugated acid (phenol) of the emitter exists as pure enol tautomer.

Journal of the American Chemical Society 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 C5H10O2S, Application In Synthesis of 19788-49-9.

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