123844-20-2

Usage

Uses

Used in Organic Synthesis:
Ethylcyclopropylpropiolate is used as a key intermediate in the synthesis of complex organic molecules, leveraging its reactivity with nucleophiles and its ability to participate in various chemical transformations.
Used in Pharmaceutical Industry:
Ethylcyclopropylpropiolate is employed as a building block in the preparation of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, ethylcyclopropylpropiolate is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, due to its capacity to form stable and effective compounds.
Used in Chemical Research:
Ethylcyclopropylpropiolate serves as a valuable research tool in chemical laboratories, enabling scientists to explore new reaction pathways and develop innovative synthetic methods.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 122244-78-4 1,1-dibromo-2-cyclopropylehylene 
• 7394-16-3 diethyl 2?(cyclopropanecarbonyl)malonate 
• 105-53-3 diethyl malonate 
• 2062-29-5 4-Phenyl-2-(trifluoromethyl)-1,3-oxazol-5(2H)-on 
• 6746-94-7 Cyclopropylacetylene 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 943130-41-4 ethyl 5-cyclopropyl-3-phenyl-1,2-oxazole-4-carboxylate 
• 1150658-69-7 (E)-ethyl 3-cyclopropyl-3-(4-(methoxymethoxy)phenyl)-2-phenylacrylate 
• 1150658-68-6 (E)-ethyl 3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylate 
• 1058158-12-5 (S)-2-(4-cyclohexyl-phenoxymethyl)-5-cyclopropyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one 
• 1279014-26-4 (S)-5-cyclopropyl-2-(2',3'-dichlorobiphenyl-4-yloxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one 
• 1279014-27-5 (S)-5-cyclopropyl-2-(2',3'-dimethylbiphenyl-4-yloxymethyl)-2,3-dihydro-oxazole[3,2-a]pyrimidin-7-one 
• 1279015-47-2 toluene-4-sulfonic acid (S)-5-cyclopropyl-7-oxo-2,3-dihydro-7H-oxazolo[3,2-a]pyrimidin-2-ylmethyl ester 
• 1610877-41-2 (1E,5E)-1-(ethoxycarbonyl)-2-cyclopropyl-6-phenyl-1,5-hexadien-3-yne 
• 7358-93-2 3‐cyclopropyl‐2‐propynoic acid 
• 2199-44-2 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole 
• 94478-13-4 cyclopropyl 2,4-dimethyl-5-(ethoxycarbonyl)pyrrol-3-yl ketone 

Relevant academic research and scientific papers

Synthesis of 1-Substituted Cyclopropylamines via Formal Tertiary Csp3-H Amination of Cyclopropanes

A novel and facile approach to synthesis of 1-substituted cyclopropylamines via phosphine-catalyzed formal tertiary Csp3-H amination of cyclopropanes was described. The indoles, pyrroles, imidazoles, uracils, 2-pyridone, pyrimidin-4(3H)-one, and phthalimide had been proven as good aminating partners. The present protocol features transition-metal-free, excellent regioselectivity, high-atom-economy, and mild reaction conditions and a broad range of substrates. The practicability of this protocol can also be demonstrated with late-stage modification of bioactive molecules, scaled up reaction, and divergent derivatization. Notably, the method has been used in the formal synthesis of the hormone-sensitive lipase (HSL) inhibitor. The mechanistic aspects were elucidated by both experimental and computational studies.

Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons

Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.

Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.

FUSED HETEROCYCLIC COMPOUNDS AS RET KINASE INHIBITORS

Provided herein are compounds of the Formula (I): (I) and tautomers, stereoisomers and pharmaceutically acceptable salts and solvates thereof, wherein Rx, Ry, W, X, Y, Z, Ring A and (AA) have the meanings given in the specification,

Selective synthesis of trisubstituted pyrroles through the reactions of alkynyl Fischer carbene complexes with oxazolones

An efficient and simple synthesis of novel trisubstituted 1H-pyrroles 4a-qvia 1,3-dipolar cycloaddition of Δ3-trifluoromethyloxazolones 2a-d with both chromium and tungsten alkynyl Fischer carbene complexes (1a-h) is described. An unexpected and unreported -CF3 group elimination process was observed in the pyrrole structure. Our experimental and theoretical data suggested that the metal fragment may be responsible for this phenomenon. The dipolar cycloaddition proceeded efficiently to produce a single regioisomer, which was unambiguously established through NMR and single-crystal X-ray diffraction studies. Nevertheless, the reaction of alkynyl carbenes bearing an α,β,γ,δ-unsaturated moiety with excess oxazolone 2a produced a polycyclic compound 6 speculatively formed through a cascade reaction involving 1,6-, 1,4- and 1,2-nucleophilic addition steps.

SUBSTITUTED PYRROLO[2,3-D]PYRIMIDINES COMPOUNDS AS RET KINASE INHIBITORS

Provided herein are compounds of the Formula I: [INSERT FORMULA I] and tautomers, stereoisomers and pharmaceutically acceptable salts and solvates thereof, wherein R1, R2 and Ry have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including RET-associated diseases and disorders.

SUBSTITUTED PYRAZOLYL[4,3-C]PYRIDINECOMPOUNDS AS RET KINASE INHIBITORS

Provided herein are compounds of the Formula I: and tautomers and pharmaceutically acceptable salts and solvates thereof, wherein R1, R2 and R3 have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including RET-associated diseases and disorders.

HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS

The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media

Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to aff