25090-18-0

Basic information

• Product Name: piperovatine
• Synonyms: piperovatine;(2E,4E)-6-(4-Methoxyphenyl)-N-(2-methylpropyl)-2,4-hexadienamide
• CAS NO: 25090-18-0
• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.37
• Mol File: 25090-18-0.mol

Chemical Properties

• Melting Point: 115-119 °C
• Boiling Point: 474.8°Cat760mmHg
• Flash Point: 241°C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 3.5E-09mmHg at 25°C
• Refractive Index: 1.524
• PKA: 14?+-.0.46(Predicted)
• CAS DataBase Reference: piperovatine(CAS DataBase Reference)
• NIST Chemistry Reference: piperovatine(25090-18-0)
• EPA Substance Registry System: piperovatine(25090-18-0)

Safety Data

• Hazardous Substances Data: 25090-18-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Piperovatine is used as a therapeutic agent for its effects on the nervous system, particularly as a temporary depressant of motor and sensory nerve fibers and sensory nerve endings. Its ability to modulate nerve activity makes it a potential candidate for the treatment of various neurological disorders.
Used in Cardiovascular Applications:
Due to its heart poison properties, piperovatine can be utilized in the development of drugs targeting cardiovascular conditions. Its effects on the heart may provide insights into the treatment of arrhythmias or other heart-related issues.
Used in Neuromuscular Applications:
Piperovatine's action as a spinal cord stimulant in frogs suggests potential applications in neuromuscular research and the development of treatments for conditions involving muscle spasms or other neuromuscular dysfunctions.
Used in Toxicological Research:
The heart poison properties of piperovatine make it a valuable tool in toxicological research, helping to understand the mechanisms of action of various toxins and their effects on the cardiovascular system.
Used in Comparative Pharmacology:
The similarity of piperovatine's induced tonic spasm to that of strychnine offers opportunities for comparative pharmacological studies, which may lead to a better understanding of the underlying mechanisms and potential therapeutic applications.

References

Dunstan, Garnett., J. Chern. Soc., 67, 94 (1895) Price, Pinder., J. Org. Chern., 35,2568 (1970) Pharmacology: Cash., J. Chern. Soc., 67,94 (1895)

InChI:InChI=1/C17H23NO2/c1-14(2)13-18-17(19)8-6-4-5-7-15-9-11-16(20-3)12-10-15/h4-6,8-12,14H,7,13H2,1-3H3,(H,18,19)/b5-4+,8-6+

Upstream product

• 25090-20-4 6-(p-Methoxyphenyl)-hexa-trans-2-trans-4-diensaeure 
• 78-81-9 isobutylamine 
• 13540-76-6 3-(4-methoxyphenyl)prop-1-yne 
• 110922-34-4 (E)-N-(2-methylpropyl)-3-iodoacrylamide 
• 25090-19-1 methyl (2E,4E)-6-(4-methoxyphenyl)-2,4-hexadienoate 
• 696-62-8 para-iodoanisole 
• 824-94-2 p-methoxybenzyl chloride 
• 14425-64-0 4-methoxyphenethyl bromide 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 63035-45-0 1-(2-ethyltriphenylphosphine)-4-methoxybenzene iodide 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 102987-40-6 (3-(4-methoxyphenyl)prop-1-ynyl)trimethylsilane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 2749-97-5 4-methoxylphenylallene 

Downstream Products

• 83029-40-7 N-isobutyl-6-(p-methoxyphenyl)hexa-3,5-dienamide 

Relevant articles and documents

A NOVEL AND EFFICIENT METHOD TO PREPARE 3-(HETERO)ARYL-1-PROPYNES AND ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF (2E,4E)-N-(2-METHYLPROPYL)-6-(2-METHYLPROPYL)-6-(2-THIENYL)-2,4-HEXADIENAMIDE, PIPEROVATINE AND (E)-N-(2-METHYLPROPYL)-6-(4-METHOXYPHENYL)-4-HEXYN-2-ENAMIDE

Chemically pure 3-(hetero)aryl-1-propynes, 13, have been prepared in high overall yields by a novel method which involves: (a) a copper(I)-mediated cross-coupling between a halomethyl(hetero)arene, 16, and trimethylsilylethylmagnesium bromide, 17, to give a trimethylsilyl-3-(hetero)aryl-1-propyne, 18; (b) removal of the trimethylsilyl group from 18 by treatment with potassium fluoride dihydrate in DMF.One of these 1-alkynes, i.e. 3-(2-thienyl)-1-propyne, 13a, has been employed in the key step of a highly stereoselective synthesis of naturally-occurring (2E,4E)-N-(2-methylpropyl)-6-(2-thienyl)-2,4-hexadienamide, 6.On the other hand, 3-(4-methoxyphenyl)-1-propyne, 13b, has been used either in two stereoselective syntheses of another natural N-(2-methylpropyl) amide, i.e. piperovatine, 7, or in the preparation of a structural analogue of 7, i.e. (E)-N-(2-methylpropyl)-6-(4-methoxyphenyl)-4-hexyn-2-enamide, 15.

SYNTHETIC APPROACHES TO ISOBUTYLAMIDES OF INSECTICIDAL INTEREST

Syntheses of 10,11-dehydro- and 10,11-(Z)-pipercide, piperovatin, and an ene-yne, and a perfluoro-isobutylamide, illustrate the utility of hydrozirconation methodology in this area.

A NOVEL APPLICATION OF MOLYBDENUM MEDIATED DIENE SYNTHESIS IN THE PREPARATION OF PIPEROVATINE

A novel regio- and stereoselective synthesis of the dienamide piperovatine is described.This method does not suffer from problems associated with doublebond migration.