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 
• 75-07-0 acetaldehyde 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 274-09-9 Methylenedioxybenzene 
• 107-02-8 acrolein 
• 1612873-28-5 (E)-1-(benzo[d][1,3]dioxol-6-yl)-3-(dimethyl(phenyl)silyl)prop-2-en-1-ol 
• 94-58-6 dihydrosafrole 
• 120-58-1 isosafrole 
• 108-05-4 vinyl acetate 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 97476-41-0 3,4-methylenedioxy-cinnamaldehyde-oxime 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 136-72-1 piperic acid 
• 52826-25-2 3-benzo[1,3]dioxol-5-yl-acrylaldehyde-(N-phenyl oxime ) 
• 94-58-6 dihydrosafrole 
• 495-85-2 (+/-)-methysticin 
• 7031-03-0 3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 1339075-22-7 diethyl (1-(benzo[d][1,3]dioxol-5-yl)-3-(n-(benzyloxy)acetamido)propyl)phosphonate 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 

Relevant articles and documents

Dramatic Effect of γ-Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

We report a dramatic effect on product outcomes of the lithium ion enabled amino-Cope-like anionic asymmetric cascade when different γ-dienolate heteroatom substituents are employed. For dienolates with azide, thiomethyl, and trifluoromethylthiol substituents, a Mannich/amino-Cope/cyclization cascade ensues to form chiral cyclohexenone products with two new stereocenters in an anti-relationship. For fluoride-substituted nucleophiles, a Mannich/amino-Cope cascade proceeds to afford chiral acyclic products with two new stereocenters in a syn-relationship. Bromide- and chloride-substituted nucleophiles appear to proceed via the same pathway as the fluoride albeit with the added twist of a 3-exo-trig cyclization to yield chiral cyclopropane products with three stereocenters. When this same class of nucleophiles is substituted with a γ-nitro group, the Mannich-initiated cascade is now diverted to a β-lactam product instead of the amino-Cope pathway. These anionic asymmetric cascades are solvent- and counterion-dependent, with a lithium counterion being essential in combination with etheral solvents such as MTBE and CPME. By altering the geometry of the imine double bond from E to Z, the configurations at the R1 and X stereocenters are flipped. Mechanistic, computational, substituent, and counterion studies suggest that these cascades proceed via a common Mannich-product intermediate, which then proceeds via either a chair (X = N3, SMe, or SCF3) or boat-like (X = F, Cl, or Br) transition state to afford amino-Cope-like products or β-lactam in the case of X = NO2.

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.

Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

A highly regioselective reaction between allylzinc bromide reagents and α,β-unsaturated oxime ethers for the one-step synthesis of the homoallylic amines is reported. This process is a regioselective 1,2-addition reaction providing a new γ-position with carbon-carbon bond formation. Furthermore, the reaction substrates are widely applicable and can be produced in a high yield.