55038-30-7

Usage

Uses

Used in Organic Chemistry:
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide is used as a building block for the synthesis of more complex organic molecules due to its unique structure and functional groups.
Used in Pharmaceutical Research:
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide is used as a potential lead compound for the development of new drugs, given its aromatic and polyunsaturated properties, which may contribute to biological activity.
Used in Material Science:
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide is used as a component in the development of new materials, such as polymers or coatings, due to its unique chemical structure and properties.

Upstream product

• 72674-93-2 trans-piperolein B ester 
• 1393364-45-8 (E)-9-(tributylstannyl)non-8-en-1-ol 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 78-81-9 isobutylamine 
• 31333-13-8 3-nonyn-1-ol 
• 10160-28-8 8-nonyn-1-ol 
• 72674-95-4 9-(3',4'-Methylenedioxyphenyl)non-8-trans-en-1-al 
• 72674-94-3 9-(3',4'-Methylenedioxyphenyl)non-8-trans-en-1-ol 
• 190592-58-6 (10E)-11-(3',4'-methylenedioxyphenyl)-10-undecenol 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 495-76-1 piperonol 
• 120-57-0 piperonal 
• 1294008-97-1 C₂₂H₂₈O₄ 
• 1294009-00-9 C₁₉H₂₄Br₂O₂ 

Relevant academic research and scientific papers

Total Synthesis of the Endocannabinoid Uptake Inhibitor Guineensine and SAR Studies

Guineensine ((2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide) is a plant-derived natural product that inhibits reuptake of the endocannabinoid anandamide with sub-micromolar potency. We have established a highly efficient tot

Practical and efficient approach to the synthesis of guineensine

A total synthesis of guineensine, a secondary metabolite of the Piperaceae family, has been executed in 12 steps with an overall yield of 27%. Key steps in the synthesis featured novel application of a Julia-Kocienski olefination reaction which effectively constructed alkenamide skeleton. This contributes a unique approach to the synthesis of the piperamide alkaloids.

REVISED STRUCTURE AND SYNTHESIS OF PIPEROLEIN ACIDS, GUINEENSINE AND WISANINE FROM PIPER GUINEENSE

The structures of piperolein acids guineensine and wisanine have been confirmed by synthesis.UV irradiation of trans piperolein B acid ester gave the cis-isomer reported in the literature as the trans-isomer.The trans-2, trans-4 ethylenic bonds in guineensine and wisanine were introduced by reacting piperolein B aldehyde and 2-methoxy piperonal with the appropriate Wittig or Reformatsky reagent.

Synthesis of Guineensine, an Alkaloid Isolated from the Fruits of Piper guineense and P. officinarum

Wittig reaction of 8-(tetrahydro-2'-pyranyloxy)octanal (IV) with (3',4'-methylenedioxyphenyl)triphenylphosphonium bromide yields 9-(3',4'-methylenedioxyphenyl)-1-(tetrahydro-2''-pyranyloxy)non-8-trans-ene (V).V on treatment with PTS in methanol followed by subsequent oxidation with pyridinium chlorochromate affords 9-(3',4'-methyleneedioxyphenyl)non-8-trans-en-1-al (VII).VII on modified Wittig reaction with ethyl α-diethylphosphonocrotonate gives the conjugate ester (VIII) which on alkaline hydrolysis provides 13-(3',4'-methylendioxyphenyl)trideca-2,4,12-trans,trans,trans-trienoic acid (IX).IX on condensation with N-isobutylamine using POCl3 in the presence of triethylamine furnishes I.