144850-45-3

Basic information

• Product Name: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one
• Synonyms: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one
• CAS NO: 144850-45-3
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.27504
• Mol File: 144850-45-3.mol

Chemical Properties

• Melting Point: 93-94 °C(Solv: ethanol (64-17-5))
• Boiling Point: 358.8°C at 760 mmHg
• Flash Point: 162.1°C
• Appearance: /
• Density: 1.134g/cm³
• Vapor Pressure: 2.49E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one(144850-45-3)
• EPA Substance Registry System: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one(144850-45-3)

Safety Data

• Hazardous Substances Data: 144850-45-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of organic chemistry, (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one serves as a versatile building block for the synthesis of a wide range of organic molecules. Its reactivity and functional groups make it a valuable precursor for creating complex molecules with diverse applications.
Used in Research and Development:
(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one is also utilized in research and development settings, where it can be employed to study various chemical reactions and mechanisms. Its unique structure and properties make it an interesting subject for scientific investigation, potentially leading to new discoveries and advancements in the field of chemistry.
Used in Synthesis of Stiripentol Glucuronide:
(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one is used as an intermediate in the synthesis of Stiripentol Glucuronide (~90%) (S686860), which is a metabolite of Stiripentol (S686825), an epilepsy drug. Stiripentol inhibits the enzymes responsible for the metabolism of other anti-convulsant agents and has been used as co-therapy for the treatment of epilepsy, highlighting the importance of (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one in the development of medications for neurological disorders.

InChI:InChI=1/C14H16O3/c1-14(2,3)13(15)7-5-10-4-6-11-12(8-10)17-9-16-11/h4-8H,9H2,1-3H3/b7-5+

Upstream product

• 139-85-5 3,4-dihydroxybenzaldehyde 
• 120-57-0 piperonal 
• 814-16-4 diethyl (3,3-dimethyl-2-oxobutyl)phosphonate 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

• 1356965-27-9 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-19-9 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-fluorophenyl)hydrazinecarboxamide 
• 1356965-21-3 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-(tert-butyl)-N-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-13-3 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-phenyl-hydrazinecarboxamide 
• 1356965-25-7 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(2-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-17-7 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(2-methylphenyl)hydrazinecarboxamide 
• 1356965-23-5 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-15-5 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-chlorophenyl)hydrazinecarboxamide 
• 1356965-24-6 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-16-6 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-methylphenyl)hydrazinecarboxamide 
• 1356965-22-4 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-N-(4-bromophenyl)-3-(tert-butyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-14-4 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-bromophenyl)hydrazinecarboxamide 
• 1356965-26-8 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1356965-18-8 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(2,4-dichlorophenyl)hydrazinecarboxamide 

Relevant articles and documents

Vibrational spectroscopic studies, Fukui functions, HOMO-LUMO, NLO, NBO analysis and molecular docking study of (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one, a potential precursor to bioactive agents

The FT-IR and FT-Raman spectra of (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one were recorded and analyzed experimentally and theoretically. The observed experimental and theoretical wavenumbers were assigned using potential energy distribution. The NLO properties were evaluated by the determination of first and second hyperpolarizabilities of the title compound. From the frontier molecular orbital study, the HOMO centers over the entire molecule except the methyl groups, while the LUMO is over the entire molecule except the CH2 group with the dioxole ring and one of the methyl groups. From the MEP plot, it is evident that the negative region covers the carbonyl and [Formula presented] groups and the positive region is over CH2 groups. The Fukui functions are also reported. The calculated geometrical parameters are in agreement with the XRD results. From the molecular docking study, the docked ligand title compound forms a stable complex with the androgen receptor and gives a binding affinity value of??8.1?kcal/mol and the results suggest that the compound might exhibit inhibitory activity against androgen receptor.

Spectroscopic identification, structural features, Hirshfeld surface analysis and molecular docking studies on stiripentol: An orphan antiepileptic drug

Epilepsy affects approximately 50 million individual worldwide but only 70% thereof are adequately controlled by the clinically used antiepileptic agents. The chemical structure of stiripentol (STP) is significantly different from any other marketed antiepileptic drug and it is approved as an add-on medication to control the childhood epilepsy. Detailed vibrational spectroscopic features of stiripentol aided by density functional theory (DFT) computations have been explored in the current study. Furthermore, the frontier molecular orbital (FMO) analysis, distribution of electric charges on the STP molecule and natural bond orbital (NBO) analysis were investigated using DFT computations. Also, Hirshfeld surface maps of STP and its 2D fingerprint plots were studied to gain insight into different patterns of its intermolecular interactions. Moreover, molecular docking simulations were conducted to manifest the probable binding pose of stiripentol to an anticonvulsant target protein.

NBS-mediated cyclization of trans-cinnamic alcohols

An efficient and straightforward three-step synthetic route toward 2,4-disubstituted-3-bromooxetanes 5 with the trans-trans contiguous stereogenic centers is developed from functionalized chalcones 3 via NaBH 4-mediated reduction of chalcones 3

Design and synthesis of novel stiripentol analogues as potential anticonvulsants

A series of stiripentol (STP) analogues namely, 2-[(1E)-1-(1,3-benzodioxol- 5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (±)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4, 5-dihydro-1H-pyrazole-1-carboxamides (±)-8a-h, and (±)-[(5RS)-(1, 3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (±)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (±)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED 50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively).

3, 4-METHYLENEDIOXYPHENYL INHIBITORS OF GABA AMINOTRANSFERASE AND/OR GABA REUPTAKE TRANSPORTER INHIBITOR

The present invention relates to new 3,4-methylenedioxyphenyl inhibitors of GABA aminotransferase activity and/or GABA reuptake transporter activity, pharmaceutical compositions thereof, and methods of use thereof. Formula (I)

Fungicidal azole derivatives

Compounds having the formula STR1 wherein Q is STR2 R1 is C1 -C8 alkyl; R2 is C4 -C17 heterocyclic aryl, unsubstituted or substituted with one or more C1 -C6 alkyl, halo or nitro, containing a sulfur atom, a nitrogen atom, or one or two oxygen atoms; X is nitrogen; and n is 2, 3 or 4, or a stereoisomer thereof. These compounds are useful as fungicides.

Fungicidal azole derivatives

Compounds having the formula STR1 wherein Q is STR2 R1 is C1 -C8 alkyl; R2 is C6 -C18 aryl, unsubstituted or substituted with one or more C1 -C6 alkyl, halo, C1 -C6 alkoxy or C1 -C6 haloalkyl; or C4 -C17 heterocyclic aryl comprising one or more oxygen or nitrogen atoms; X is nitrogen or --CH--; and n is 2, 3 or 4, or a stereoisomer thereof, with the proviso that when Q is STR3 and X is N, then R2 is not phenyl or substituted phenyl. These compounds are useful as fungicides.

Efficient Wittig-Horner and Improved Claisen-Schmidt Synthesis of Acyclic α-Enones with a 2-Furyl or 3,4-Methylenedioxyphenyl Group at the β-Position.

The Wittig-Horner and Claisen-Schmidt syntheses of acyclic α-enanes bearing a 2-furyl or 3,4-methylenedioxyphenyl group in the β-position have been achieved using activated barium hydroxide C-200 with good yields.The Wittig-Horner reaction in homogeneous phase is shown to be more efficient than the Claisen-Schmidt condensation under interfacial solid-liquid conditions.The 1H and the 13C megnetic parameters of compounds 5 and 6 are described.The use of 1H-13C correlation spectra helped in the unambiguous assignment of the olefinic and aromatic carbons of α-enones 5a and 6a.