2286-56-8

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE is used as a synthetic intermediate for the development of pharmaceuticals, leveraging its unique chemical structure to contribute to the creation of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE serves as a key intermediate in the synthesis of agrochemicals, potentially enhancing crop protection and yield through the development of novel compounds with specific pesticidal or herbicidal properties.
Used in Organic Chemistry Research:
ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE is utilized as a research compound in organic chemistry, where its structural features are explored for potential reactions and applications in the synthesis of complex organic molecules.
It is crucial to handle ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE with care due to its potential health and safety risks, ensuring proper safety measures are in place during its use in various applications.

InChI:InChI=1/C13H11NO4/c1-2-16-13(15)10(7-14)5-9-3-4-11-12(6-9)18-8-17-11/h3-6H,2,8H2,1H3/b10-5+

Upstream product

• 120-57-0 piperonal 
• 64-17-5 ethanol 
• 105-56-6 ethyl 2-cyanoacetate 
• 51066-70-7 2-cyano-3-(3',4'-methylenedioxy-1'-phenyl)acrylic acid 
• 14683-73-9 N,N'-benzo[1,3]dioxol-5-ylmethanediyl-bis-acetamide 
• 4543-59-3 1,2-bis(3,4-dioxymethylenephenyl)ethane-1,2-diol 

Downstream Products

• 19313-82-7 (E)-3-(benzo[d][1,3]dioxol-5-yl)-2-cyano-N-phenylacrylamide 
• 49711-55-9 (E)-3-(benzo[d][1,3]dioxol-5-yl)-2-cyanoacrylic acid 
• 1334176-96-3 (Z)-7-(benzo[d][1,3]dioxol-5-ylmethylene)-3-phenyl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-one 
• 133405-30-8 2-Amino-4-benzo[1,3]dioxol-5-yl-6-thiophen-2-yl-isophthalonitrile 
• 133379-54-1 3-Amino-5-benzo[1,3]dioxol-5-yl-biphenyl-2,4-dicarbonitrile 

Relevant academic research and scientific papers

A novel Golgi mannosidase inhibitor: Molecular design, synthesis, enzyme inhibition, and inhibition of spheroid formation

Effective chemotherapy for solid cancers is challenging due to a limitation in permeation that prevents anticancer drugs from reaching the center of the tumor, therefore unable to limit cancer cell growth. To circumvent this issue, we planned to apply the drugs directly at the center by first collapsing the outer structure. For this, we focused on cell–cell communication (CCC) between N-glycans and proteins at the tumor cell surface. Mature N-glycans establish CCC; however, CCC is hindered when numerous immature N-glycans are present at the cell surface. Inhibition of Golgi mannosidases (GMs) results in the transport of immature N-glycans to the cell surface. This can be employed to disrupt CCC. Here, we describe the molecular design and synthesis of an improved GM inhibitor with a non-sugar mimic scaffold that was screened from a compound library. The synthesized compounds were tested for enzyme inhibition ability and inhibition of spheroid formation using cell-based methods. Most of the compounds designed and synthesized exhibited GM inhibition at the cellular level. Of those, AR524 had higher inhibitory activity than a known GM inhibitor, kifunensine. Moreover, AR524 inhibited spheroid formation of human malignant cells at low concentration (10 μM), based on the disruption of CCC by GM inhibition.

Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation

Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.

Knoevenagel condensation of aldehydes with active methylene compounds catalyzed by MgC2O4/SiO2 under microwave irradiation and solvent-free conditions

MgC2O4/SiO2 catalyzes the efficient Knoevenagel condensation of aldehydes with active methylene compounds in solvent-free conditions under microwave irradiation to give alkenes derivatives in excellent yields. MgC2/s

On-column solvent-free oxidative cleavage reactions of vicinal diols by silica gel and paraperiodic acid: Application to in-situ sequential oxidation and Knoevenagel reactions

An on-column solvent-free oxidative cleavage reaction of vicinal diols by paraperiodic acid supported on silica gel at room temperature is described. The resulting pure carbonyl compounds are prepared in good to excellent yields with short reaction times. The cleavage reactions proceed under mild conditions, which avoids further cyclization reactions of the product dialdehydes. This method is also used for sequential oxidation and Knoevenagel reactions to prepare condensation products in good yields by using paraperiodic acid on a mixed bed of alumina and silica gel. The on-column solvent-free oxidative cleavage reaction of vicinal diols by paraperiodic acid supported on silica gel at room temperature is investigated. This approach is applied to an oxidation andKnoevenagel reaction sequence by using a mixed bed of alumina and silica gel to give condensation products in good yields. Copyright

Efficient asymmetric synthesis of 4H-chromene derivatives through a tandem michael addition-cyclization reaction catalyzed by a salen-cobalt(II) complex

The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates. Moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee) were obtained with a chiral salen-cobalt(II) complex. This process was air tolerant and easily performed, which provides an efficient method for the synthesis of chiral 4H-chromene derivatives. The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates catalyzed by a chiral salen-cobalt(II) complex with moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee).

Microwave-enhanced Knoevenagel condensation catalysed by NH 2so3NH4

Ammonium sulphamate catalyses the efficient Knoevenagel condensation of aromatic aldehydes 1 with active methylene compounds in solvent-free conditions under microwave irradiation to give arylidene derivatives 3. The yields are excellent and purity is hig

Reaction of (E)-3-(Benzo[d][1,3]dioxol-5-yl)-2- cyanoacryloyl chloride with nucleophilic reagents containing nitrogen and sulfur

(E)-3-(Benzo[d][1,3]dioxol-5-yl)-2-cyanoacryloyl chloride was reacted with nucleophilic reagents containing nitrogen and sulfur to give new acryloyl amides, imides, thioesters, and heterocyclic systems. Some of these products showed moderate activities ag

Uses of piperonal in the synthesis of novel prop-2-enoyl amides, esters, heterocyclic systems and study of their antibacterial activities

Novel (E)-3-(benzold)[1,3]dioxol-5-yl)-2-cyanoacryloyl chloride 4 was condensed with several mono-; 1,2-; 1,3- and 1,4-bi-nucleophilic reagents containing nitrogen and oxygen to give new 2-propenoylamide and ester derivatives. Some of these amides cyclise

Clean synthesis of ethyl α-cyanocinnamates catalysed by hexadecyltrimethyl ammonium bromide in aqueous media

An efficient and convenient approach to the synthesis of ethyl α-cyanocinnamates in water using hexadecyltrimethyl ammonium bromide (HTMAB) as the phase-transfer catalyst (10 mol %) is described. This method provides several advantages such as neutral con

Towards organo-click reactions: Development of pharmaceutical ingredients by using direct organocatalytic bio-mimetic reductions

Economic and environmentally friendly bio-mimetic one-pot three and four-component Knoevenagel-hydrogenation (K-H), five-component Knoevenagel-hydrogenation-alkylation (K-H-A) and six-component Knoevenagel-hydrogenation-alkylation-Huisgen cycloaddition (K-H-A-HC) reactions of aldehydes, CH-acids, o-phenylenediamine, alkyl halides and azides using proline, proline-metal carbonate and proline-metal carbonate-Cu I-catalysis, respectively have been developed. Many of K-H and K-H-A compounds have direct application in pharmaceutical chemistry. The Royal Society of Chemistry.