Synonyms:ethyl propiolate
99%, *data from raw suppliers
EthylPropargylate *data from reagent suppliers
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There total 13 articles about Ethyl propiolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 86.7%
Reference yield: 24.0%
Reference yield:
The study focuses on the synthesis of substituted 2-azabicyclo[3.2.1]octadienes, which are significant in the creation of natural products and biologically active compounds, through the ring expansion of substituted norbornadienes using toluenesulfonyl azide. The researchers explored the regioselectivity of the cycloaddition/rearrangement process with various mono- and disubstituted norbornadienes, finding that both types could be converted into the bicyclooctadiene ring system with high regiocontrol and in moderate to excellent yields. The study also investigated the impact of different substituent groups on the reaction's outcome, noting that electron-withdrawing groups resulted in little to no product, while hydroxymethyl derivatives provided a moderate yield of a single regioisomer. The synthesized 2-azabicyclo[3.2.1]octadienes can be further modified to yield highly substituted derivatives of the 2-azabicyclo[3.2.1]octane ring system, which is prevalent in natural products and pharmacologically active molecules, thus providing a valuable route for the synthesis of these complex structures.
The research presents a novel and efficient approach to synthesizing 2,3,4a,5-tetrahydro-1H-pyrazino[1,2-a]quinoline-4,6-diones, which are constrained arylpiperazinones of interest in medicinal chemistry due to their potential as G-protein-coupled receptor (GPCR) ligands. The key innovation is a one-pot, three-step reaction sequence involving 1,4-addition, lactamization, and intramolecular nucleophilic aromatic substitution (SNAr) to form the tricyclic ring system. The synthesis begins with the conversion of ortho-fluorobenzaldehydes to propargylic alcohols using lithium diisopropylamide (LDA) and ethyl propiolate, followed by rearrangement to enones with triethylamine. These enones then react with ethylenediamine to yield the desired tetrahydro-pyrazinoquinoline-dione compounds. The study successfully synthesized four examples of these compounds, demonstrating the versatility of the method with different substituents on the aromatic ring.
The research explores a new method for synthesizing reserpine, a complex alkaloid with significant pharmaceutical importance. The study aims to develop a general synthetic methodology for constructing the hydroisoquinoline core structure found in reserpine, using amino-Claisen rearrangements of zwitterionic N-vinylisoquinuclidenes. Key chemicals used in this research include N-(indolylethyl)isoquinuclidenes, ethyl propiolate, and tert-butyl propiolate. The researchers demonstrated that these rearrangements can efficiently produce cis-fused hydroisoquinolines, which are crucial intermediates in the synthesis of reserpine. They also showed that the resulting hydroisoquinoline derivatives can undergo Wenkert cyclization to form pentacyclic systems resembling the natural product skeleton of reserpine. The study concludes that the combination of zwitterionic amino-Claisen rearrangements and Wenkert-type cyclizations offers a promising and efficient route for constructing the complex reserpine skeleton, with potential for further optimization and application in the synthesis of other Rauwolfia alkaloids.
The research focuses on the synthesis of specifically deuterated 1,3-diethoxy-carbonylallylidene-triphenylphosphonium ylides. The purpose was to develop methods for introducing deuterium labels in the ?- and ?-positions of the allylidene-phosphonium ylide without deuterium scrambling. In the research, ethyl propynoate serves as a key starting material for the synthesis of deuterated compounds. It is used in the Michael addition reaction to produce the ?-deuterated phosphonium ylide and also as a reactant in the synthesis of ethyl 3-deuteriopropynoate, which is crucial for the ?-deuteration process. Deuterium oxide (D2O) plays a vital role in the deuterium exchange reactions. It is used to introduce deuterium atoms into the molecules, specifically in the synthesis of ethyl 3-deuteriopropynoate and in the acid-catalyzed deuterium exchange to produce the ?-deuterated phosphonium ylide. Sodium deuteroxide (NaOD) acts as a base in the deuterium exchange process. It is used to facilitate the deuterium exchange reactions and to neutralize any acid present, ensuring that the deuterium atoms are retained in the final products. Tetrabutylammonium iodide (TBAI) functions as a phase-transfer catalyst. It helps to transfer reactants between the organic and aqueous phases, enhancing the efficiency of the deuterium exchange reactions in the synthesis of ethyl 3-deuteriopropynoate. For ?-deuteration, ethyl propynoate was treated with deuterium oxide under phase transfer conditions to synthesize ethyl 3-deuteriopropynoate, which was then reacted with the ylide to produce the ?-deuterated phosphonium ylide. For ?-deuteration, the ylide was subjected to acid-catalyzed, regiospecific deuterium exchange with deuterium oxide and deuterium chloride, followed by base treatment to avoid deuterium loss. The methods resulted in high deuterium incorporation (>90%) and good yields (66-80%), providing a reliable way to introduce deuterium labels for further studies.
The study focuses on the synthesis, characterization, and reactivity of rhodium(III) complexes with N-boranyl-1,3,5-triaza-7-phosphaadamantane (N–B–PTA(BH3)) ligands. The reaction of N–B–PTA(BH3) with [CpRhCl(l-Cl)]2 yields complexes [CpRh{N–B–PTA(BH3)}Cl2] (3) or [CpRh{N–B–PTA(BH3)}2Cl]Cl (5), containing one or two P-bonded boronated PTA ligands. The hydride [CpRh{N–B–PTA(BH3)}H2] (8) was also obtained by reaction with NaBH4. These complexes can undergo hydrolysis to produce dihydrogen and H3BO3, along with PTA derivatives. Furthermore, the reaction of complex 8 with electron-poor alkynes results in the formation of alkene complexes [Cp*Rh{N–B–PTA(BH3)}(g2-CH2 = CHR)] without affecting the N–BH3 moiety. The X-ray crystal structures of complexes 3 and 10 were determined and discussed, providing insights into the coordination chemistry and potential applications of these water-soluble rhodium complexes.
The study presents the second total synthesis of Brevisamide, a marine cyclic ether alkaloid derived from Karenia brevis. The streamlined synthesis was achieved in 21 steps with a 5.2% overall yield, featuring a key SmI2 reductive cyclization step to access the tetrasubstituted pyran core. Key chemicals used in the study include monobenzyl protected-1,4-butane diol, which served as the starting material for the synthesis of pyran 3; ethyl propiolate, used in the 1,4-addition to form intermediate 9; and phosphonate ester 2, synthesized through a series of reactions including a Wittig reaction and an Arbuzov reaction, which was crucial for the Horner-Wadsworth-Emmons reaction to assemble the western C1-C4 and eastern C5-C15 fragments. The purpose of these chemicals was to construct the complex structure of Brevisamide through a series of strategic synthetic steps, ultimately leading to the successful synthesis of the natural product.
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