16862-05-8

Usage

Uses

1. Used in Organic Synthesis:
Methyl 3-(2-Thienyl)propanoate is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for the creation of more complex molecules, which can be utilized in different applications such as pharmaceuticals, agrochemicals, and materials science.
2. Used in Pharmaceutical Industry:
Methyl 3-(2-Thienyl)propanoate is used as a key component in the development of new pharmaceutical compounds. Its unique chemical structure can be exploited to design and synthesize novel drugs with potential therapeutic applications, such as those targeting specific diseases or conditions.
3. Used in Agrochemical Industry:
In the agrochemical industry, Methyl 3-(2-Thienyl)propanoate can be used as a starting material for the synthesis of new pesticides, herbicides, or other crop protection agents. Its unique properties may contribute to the development of more effective and environmentally friendly products.
4. Used in Materials Science:
Methyl 3-(2-Thienyl)propanoate can also be utilized in the development of new materials with specific properties, such as improved conductivity, stability, or other characteristics. Its unique structure can be incorporated into the design of advanced materials for various applications, including electronics, energy storage, and more.

InChI:InChI=1/C8H10O2S/c1-10-8(9)5-4-7-3-2-6-11-7/h2-3,6H,4-5H2,1H3

Upstream product

• 67-56-1 methanol 
• 5928-51-8 3-(2-thienyl)propanoic acid 
• 79-22-1 methyl chloroformate 
• 26359-21-7 3-(thiophen-2-yl)propanal 
• 15690-25-2 3-(2-thienyl)acrylic acid 
• 77998-66-4 C₄H₃S^(1-) 
• 292638-85-8 acrylic acid methyl ester 
• 1124-65-8 3-(2-thienyl)-2-propenoic acid 
• 5834-04-8 3-(2-thienyl)-propanoic acid chloride 
• 57502-38-2 methyl (E)-3-(2-thienyl)propenoate 

Downstream Products

• 133040-04-7 2-butyl-1-(4-carbomethoxybenzyl)-5-<2-carbomethoxy-1-hydroxy-3-(2-thienyl)propyl>imidazole 
• 133485-58-2 methyl 3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-3-hydroxy-2-[(thien-2-yl)methyl]propanoate 
• 19498-72-7 3-thiophen-2-yl-propan-1-ol 
• 133485-83-3 (E)-3-[2-n-butyl-1-{(2-trifluoromethylphenyl)methyl}-1H-imidazol-5-yl]-2-(thien-2-yl)methyl-2-propenoic acid 
• 149543-81-7 methyl (E)-3-[2-n-butyl-1-{(4-carbomethoxy-3-hydroxyphenyl)methyl}-1H-imidazol-5-yl]-2-(thien-2-yl)methyl-2-propenoate 

Relevant academic research and scientific papers

Structure–Property Relationships in Bithiophenes with Hydrogen-Bonded Substituents

The use of crystal engineering to control the supramolecular arrangement of π-conjugated molecules in the solid-state is of considerable interest for the development of novel organic electronic materials. In this study, we investigated the effect of combining of two types of supramolecular interaction with different geometric requirements, amide hydrogen bonding and π-interactions, on the π-overlap between calamitic π-conjugated cores. To this end, we prepared two series of bithiophene diesters and diamides with methylene, ethylene, or propylene spacers between the bithiophene core and the functional groups in their terminal substituents. The hydrogen-bonded bithiophene diamides showed significantly denser packing of the bithiophene cores than the diesters and other known α,ω-disubstituted bithiophenes. The bithiophene packing density reach a maximum in the bithiophene diamide with an ethylene spacer, which had the smallest longitudinal bithiophene displacement and infinite 1D arrays of electronically conjugated, parallel, and almost linear N?H???O=C hydrogen bonds. The synergistic hydrogen bonding and π-interactions were attributed to the favorable conformation mechanics of the ethylene spacer and resulted in H-type spectroscopic aggregates in solid-state absorption spectroscopy. These results demonstrate that the optoelectronic properties of π-conjugated materials in the solid-state may be tailored systematically by side-chain engineering, and hence that this approach has significant potential for the design of organic and polymer semiconductors.

Thiophene-based water-soluble fullerene derivatives as highly potent antiherpetic pharmaceuticals

Here we report the Friedel-Crafts arylation of chlorofullerenes C60Cl6 and C70Cl8 with thiophene-based methyl esters. While C60Cl6 formed expected Cs-C60R5Cl products, C70Cl8 demonstrated a tendency for both substitution of chlorine atoms and addition of an extra thiophene unit, thus forming Cs-C70R8 and C1-C70R9H compounds. The synthesized water-soluble C60 and C70 fullerene derivatives with thiophene-based addends demonstrated high activity against a broad range of viruses, including human immunodeficiency virus, influenza virus, cytomegalovirus, and herpes simplex virus. The record activity of C70 fullerene derivatives against herpes simplex virus together with low toxicity in mice makes them promising candidates for the development of novel non-nucleoside antiherpetic drugs.

Industrial preparation method of 2-ethylamine-heterocyclic derivative

The invention provides an industrial preparation method of a 2-ethylamine-heterocyclic derivative. The method is characterized in that a heteroaryl derivative and 2-substituent ethylene react to produce a 2-(2-cyanoethyl)-heterocyclic derivative, a 2-acetate-heterocyclic derivative and a 2-(3-butyl ketone)-heterocyclic derivative separately. The production method is simple and different from complicated production modes and harsh production conditions in the prior art. By means of the industrial preparation method, synthesis of a target product can be achieved by one step. As the production technology and synthetic route are optimized through the preparation method, in the production process, few side reactions occur, the aftertreatment is convenient, the production condition is mild, and the preparation method is suitable for an industrialized production mode.

Thiophenium-ylides: Synthesis and reactivity

The reaction of propanedioic acid, 2-diazo-1,3-bis(1,1-dimethylethyl) ester (di-tert-butyl diazomalonate) with a series of cyclopenta[b]thiophenes in the presence of catalytic rhodium acetate was studied. The resulting SC ylides underwent a rearrangement to form a heterocycle with different topology; thialene, in very low yields. Experimental and spectral data for all compounds are provided.

Visible light-induced selective generation of radicals from organoborates by photoredox catalysis

A new strategy for the generation of carbon-centered radicals via oxidation of alkyl-, allyl-, benzyl- and arylborates by visible-light-driven single electron transfer (SET) photoredox catalysis has been established. The generated radicals smoothly react with TEMPO and electron-deficient alkenes to afford C-O and C-C coupling products, respectively. In this radical initiating system, cyclic organo(triol)borates turn out to be useful radical precursors.

N-Heterocyclic carbene-catalyzed oxidations

N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.

N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters

(Chemical Equation Presented) N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.

Heteroaromatic side-chain analogs of pregabalin

A series of heteroaromatic analogs of pregabalin has been identified that possess anticonvulsant activity in the DBA/2 mouse model. The methods of synthesis and preliminary pharmacology are discussed herein.

Synthesis of selective SRPK-1 inhibitors: Novel tricyclic quinoxaline derivatives

SR protein-specific kinase-1 (SRPK-1) has been identified as a validated target for hepatitis B virus (HBV). A series of novel tricyclic quinoxaline derivatives was designed and synthesised as potential kinase inhibitory antiviral agents and was found to be active and selective for SRPK-1 kinase. Most of these novel compounds have drug-like properties according to experimentally determined Log P and Log S values.

3-heteroarylalkyl substituted gaba analogs

The invention is a novel series of compounds which are useful in the treatment of epilepsy, faintness attacks, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), and inflammation, especially arthritis. A pharmaceutical composition containing a compound of the invention as well as methods of preparing the compounds and novel intermediates useful in the preparation of the final compounds are included.