35285-25-7

Basic information

• Product Name: Solenopsin A
• Synonyms: Solenopsin A;(2S)-2β-Methyl-6α-undecylpiperidine;(2S)-2β-Undecyl-6α-methylpiperidine;2β-Methyl-6α-undecylpiperidine;Solenopsine A
• CAS NO: 35285-25-7
• Molecular Formula: C₁₇H₃₅N
• Molecular Weight: 253.4665
• Mol File: 35285-25-7.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 320.1°Cat760mmHg
• Flash Point: 150.9°C
• Appearance: /
• Density: 0.821g/cm³
• Vapor Pressure: 0.000324mmHg at 25°C
• Refractive Index: 1.445
• PKA: 10.78±0.10(Predicted)
• CAS DataBase Reference: Solenopsin A(CAS DataBase Reference)
• NIST Chemistry Reference: Solenopsin A(35285-25-7)
• EPA Substance Registry System: Solenopsin A(35285-25-7)

Safety Data

• Hazardous Substances Data: 35285-25-7(Hazardous Substances Data)

Usage

General Description

Solenopsin A is a chemical compound found in the venom of fire ants, specifically the species Solenopsis invicta. It is a piperidine alkaloid that acts as a potent cytolytic and hemolytic agent, causing cell membrane disruption and cell lysis. Solenopsin A has been found to have antimicrobial properties, inhibiting the growth of both bacteria and fungi. Research has also shown that solenopsin A has potential as a novel anti-cancer agent, as it can induce apoptosis in human cancer cells. Additionally, solenopsin A has been studied for its potential use as an anti-inflammatory and analgesic compound, making it a target for drug development and further exploration of its therapeutic applications.

InChI:InChI=1/C17H35N/c1-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16(2)18-17/h16-18H,3-15H2,1-2H3/t16-,17-/m0/s1

Upstream product

• 126523-61-3 Methyl 2-Methyl-6-undecylpiperidine-1-carboxylate 
• 109-06-8 α-picoline 
• 113999-43-2 (2R^*,3S^*)-N-hydroxy-3-(trimethylsilyl)-4-penten-2-amine 
• 113999-29-4 1-hydroxy-cis-2-methyl-6-undecyl-1,2,5,6-tetrahydropyridine 
• 112-16-3 n-dodecanoyl chloride 
• 693-67-4 bromoundecane 
• 132410-16-3 1-(tert-butoxycarbonyl)-6-methyl-2-n-undecyl-1,2,3,4-tetrahydropyridine 
• 132438-34-7 1-(tert-butoxycarbonyl)-4-chloro-6-methyl-2-n-undecyl-1,2-dihydropyridine 
• 132410-10-7 1-(tert-butoxycarbonyl)-4-chloro-cis-6-methyl-2-n-undecyl-1,2,5,6-tetrahydropyridine 
• 4775-98-8 δ-caprolactam 
• 888745-46-8 (R)-Undeca-1,10-diene-4,8-diol 
• 111512-38-0 4,8-dihydroxy-1,10-undecanediene 
• 917-54-4 methyllithium 
• 160549-82-6 tert-butyl (2R,6R)-(-)-2-methyl-6-undecyl-piperidine-1-carboxylate 

Relevant articles and documents

Stereoselective synthesis of 2,6-: Trans -4-oxopiperidines using an acid-mediated 6- endo-trig cyclisation

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.

Removal of the pyridine directing group from α-substituted N-(pyridin-2-yl)piperidines obtained via directed Ru-catalyzed sp3 C-H functionalization

Two strategies, "hydrogenation-hydride reduction" and "quaternization-hydride reduction", are reported that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed sp3 C-H functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally equally effective. Only in the case of 2,6-disubstituted piperidines, could the "quaternization-hydride reduction" strategy not be used. The "hydrogenation-hydride reduction" protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (±)-solenopsin A (trans diastereoisomer) and (±)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire ant alkaloids could be determined via VCD spectroscopy.