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

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

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 
• 97476-41-0 3,4-methylenedioxy-cinnamaldehyde-oxime 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 110-46-3 isopentyl nitrite 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 108-05-4 vinyl acetate 
• 120-58-1 isosafrole 
• 94-58-6 dihydrosafrole 
• 274-09-9 Methylenedioxybenzene 
• 107-02-8 acrolein 
• 821775-37-5 trans-3-(4,5-methylenedioxyphenyl)-2-propene ethylene acetal 

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 
• 94-62-2 Piperine 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 116513-12-3 5-((1R,3aS,4R,6aS)-4-Benzyloxymethyl-tetrahydro-furo[3,4-c]furan-1-yl)-benzo[1,3]dioxole 
• 116513-08-7 (1R,3aS,4R,7aR)-4-Benzo[1,3]dioxol-5-yl-1-benzyloxymethyl-tetrahydro-furo[3,4-c]pyran-6-one 
• 116537-62-3 (1R,3aS,4R,7R,7aS)-4-Benzo[1,3]dioxol-5-yl-1-benzyloxymethyl-7-hydroxy-tetrahydro-furo[3,4-c]pyran-6-one 
• 116513-07-6 (6R,6aS,9R,9aS)-6-Benzo[1,3]dioxol-5-yl-9-benzyloxymethyl-3,3-dimethyl-6a,7,9,9a-tetrahydro-6H-furo[3',4':4,5]pyrano[2,3-d][1,3]dioxin-1-one 

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.

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.

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.

Palladium-Catalyzed Formylation of Alkenylzinc Reagents with S-(4-Nitrophenyl) Thioformate

We report the synthesis of enal compounds by palladium-catalyzed formylation of alkenylzinc reagents with S-(4-nitrophenyl) thioformate. Various functional groups were tolerated in the present reaction. 1H NMR experiments revealed that the products had a non-protected formyl group, which can be utilized for further C–C bond formation reactions. We successfully achieved the one-pot synthesis of a 1,5-diene-3-ol compound via sequential formylation and allylation.

Hendrickson reagent induced rearrangement of aryl propargyl alcohols to α,β-unsaturated aldehydes

The Hendrickson reagent (triphenylphosphonium anhydride trifluoromethanesulfonate), prepared from the reaction of triphenylphosphine oxide (Ph3PO) and triflic anhydride (Tf2O) (2:1 stoichiometry), promotes dehydrations and various coupling reactions. The reagent has been used to transform oximes to nitriles and to prepare esters, amides and many other functional groups through the intermediacy of an alkoxyphosphonium salt. The reagent proved useful in heterocycle synthesis of thiazolines, imidazolines, quinoline precursors, isoquinolines, β-carbolines, phenanthridines, 11H-indolo[3,2-c]quinolines, quinoline-lactones, furoquinolinones, and indolizino[1,2-b]quinolin-9(11H)-ones. Moreover, the reagent has been key to the successful total synthesis of several natural products. Aryl propargyl alcohols with a terminal α-acetylenic group undergo rapid conversion to the corresponding α,β-unsaturated aldehydes at room temperature in dichloromethane in the presence of one equivalent of triphenylphosphonium anhydride trifluoromethanesulfonate. The reaction involved adding freshly distilled Tf2O (1.0 mmol) to a solution of Ph3PO (2.0 mmol) in CH2Cl2 (10 mL) at 0oC under N2 atmosphere. After stirring for 10 min, the propargyl alcohol (1.0 mmol) was added as a CH2Cl2 solution (2 mL), followed by the addition of water and Et3N (2.0 mmol) and further stirring at room temperature for 1h. Subsequent workup with 5% NaHCO3 (20 mL) and purification afforded α,β-unsaturated aldehydes. Eighteen aryl propargyl alcohol substrates with a terminal α-acetylenic group were transformed in good to excellent yields (71-85%) to enals. The methodology proved successful with secondary and tertiary alcohols with stereoselectivity favouring exclusively the E isomer. All the synthesized compounds are known and were characterized (1H,13C, and M.P) and compared to literature values. The method offers several advantages such as exclusive stereoselectivity, short reaction time, good yield, mild reaction conditions, and simple operational procedure.

Chemoselective hydrogen peroxide oxidation of primary alcohols to aldehydes by a water-soluble and reusable iron(iii) catalyst in pure water at room temperature

Hydrogen peroxide oxidation of primary alcohols to aldehydes is described, which is catalyzed by a novel, reusable and water-soluble FeCl3 complex in situ-formed with quaternary ammonium salt-functionalized 8-aminoquinoline. This reaction exhibits unique chemoselectivity and broad functional-group tolerance, and it can operate efficiently in pure water at room temperature.

Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.

Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis

The development of semi-stabilized, stabilized, and functionalized ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy separation of water-soluble phosphine oxides. The development of a mild organocatalytic process for the Wittig reaction and extension toward the preparation of reporter stilbenes under biological conditions are also described. Applications toward the preparation of biologically active natural products and derivatives are discussed.