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
• Article Data: 8

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

Description

(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one is an organic compound characterized by its unique molecular structure, which features a pentenone core with two methyl groups at the 4th position, a 3,4-methylenedioxyphenyl group attached to the 1st position, and an E-configuration of the double bond. (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one is known for its distinct chemical properties and potential applications in various fields.

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 this compound 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

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

Downstream Products

• 1356965-29-1 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](phenyl)methanone 
• 1356965-30-4 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](4-bromophenyl)methanone 
• 1356965-31-5 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](4-chlorophenyl)methanone 
• 1356965-32-6 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](4-methylphenyl)methanone 
• 1356965-33-7 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](2-methylphenyl)methanone 
• 1356965-34-8 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](2,4-dichlorophenyl)methanone 
• 1356965-18-8 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(2,4-dichlorophenyl)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 
• 1356965-14-4 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-bromophenyl)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 
• 1356965-16-6 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-methylphenyl)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 
• 1356965-15-5 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-chlorophenyl)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 

Relevant articles and documents

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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.

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).