58095-77-5

Basic information

• Product Name: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)
• Synonyms: 3-(3',4'-methylenedioxyphenyl)prop-2-enal;(E)-3-(benzo[d][1,3]dioxol-5-yl)acrylaldehyde;(E)-3-(benzo[d][1,3]dioxol-6-yl)acrylaldehyde;(E)-3-(benzo[1,3]dioxol-5-yl)acrylaldehyde;(2E)-3-(3,4-methylenedioxyphenyl)propenal;(E)-3-(3,4-methylenedioxyphenyl)prop-2-en-1-al
• CAS NO: 58095-77-5
• Molecular Formula: C10H8O3
• Molecular Weight: 176.17
• Mol File: 58095-77-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 326.3±11.0 °C(Predicted)
• Density: 1.268±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(58095-77-5)
• EPA Substance Registry System: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(58095-77-5)

Safety Data

• Hazardous Substances Data: 58095-77-5(Hazardous Substances Data)

Usage

Description

2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI), also known as (E)-3,4-Methylenedioxycinnamaldehyde, is an organic compound that serves as a crucial intermediate in the synthesis of various compounds. It is characterized by its unique molecular structure, which includes a propenal group, a dimethyl-benzodioxol group, and an E-configuration double bond.

Uses

Used in Pharmaceutical Industry:
2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI) is used as an intermediate in the synthesis of 3-Hydroxyhispidin (H943133), a derivative of Hispidin (H436450). Hispidin is a naturally occurring compound that serves as a precursor to fungal luciferin, which is responsible for the luminosity observed in certain mushrooms. 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI) is of interest due to its potential applications in the development of new pharmaceuticals and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI) is utilized as a key building block for the creation of various complex organic molecules. Its unique structure and functional groups make it a valuable component in the synthesis of a wide range of compounds, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries.
Used in Research and Development:
2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI) is also used in research and development settings, where it can be employed to study the properties and reactivity of similar compounds. This can lead to a better understanding of the underlying chemical principles and potentially the discovery of new synthetic routes and applications for related compounds.

Upstream product

• 120-57-0 piperonal 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 495-76-1 piperonol 
• 7031-03-0 3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol 
• 27064-04-6 S-(4-nitrophenyl) thioformate 
• 5208-87-7 1'-hydroxysafrole 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 1612873-28-5 (E)-1-(benzo[d][1,3]dioxol-6-yl)-3-(dimethyl(phenyl)silyl)prop-2-en-1-ol 
• 123261-70-1 (E)-5-(3,3-diethoxy-1-propenyl)-1,3-benzodioxole 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 107-02-8 acrolein 
• 821775-37-5 trans-3-(4,5-methylenedioxyphenyl)-2-propene ethylene acetal 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 

Downstream Products

• 1339075-22-7 diethyl (1-(benzo[d][1,3]dioxol-5-yl)-3-(n-(benzyloxy)acetamido)propyl)phosphonate 
• 495-85-2 (+/-)-methysticin 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 
• 880548-03-8 N-[(1R,2R,6R)-6-(1,3-benzodioxol-5-yl)-2-hydroxy-3-cyclohexen-1-yl]carbamic acid methyl ester 

Relevant articles and documents

Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis

Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.

Compound with piperine skeleton structure as well as preparation and application thereof

The invention discloses a compound with a piperine skeleton structure as well as preparation and application of the compound, wherein the structural formulas of the compound are shown as a formula I-1and a formula I-2; in the formulas, R1 is hydrogen, halogen, nitryl or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, C1-C5 straight-chain or branched-chain alkyl and C1-C5 alkoxy; R2 is hydrogen, halogen, nitro or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, phenyl, aryl and aromatic heterocyclic group, or substituted or unsubstituted C1-C5 straight-chain or branched-chain alkyl, or substituted or unsubstituted C1-C5 alkoxy, or substituted or unsubstituted C6-C30 aryl, fused ring and fused heterocyclic ring. As a chitinase inhibitor, the compound provided by the invention has the advantages of high activity, good broad spectrum and easiness in synthesis, and shows excellent insecticidal ability and insecticidal spectrum.

Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies

Piperine has been associated with neuroprotective effects and monoamine oxidase (MAO) inhibition, thus being an attractive scaffold to develop new antiparkinsonian agents. Accordingly, we prepared a small library of piperine derivatives and screened the inhibitory activities towards human MAO isoforms (hMAO-A and hMAO-B). Structure-activity relationship (SAR) studies pointed out that the combination of α-cyano and benzyl ester groups increased both potency and selectivity towards hMAO-B. Kinetic experiments with compounds 7, 10 and 15 indicated a competitive hMAO-B inhibition mechanism. Compounds 15 and 16, at 10 μM, caused a small but significant decrease in P-gp efflux activity in Caco-2 cells. Compound 15 stands out as the most potent piperine-based hMAO-B inhibitor (IC50 = 47.4 nM), displaying favourable drug-like properties and a broad safety window. Compound 15 is thus a suitable candidate for lead optimization and the development of multitarget-directed ligands.