21446-46-8

Usage

Chemical Properties

Cyrstalline Solid

Uses

A metabolite of Nicotine

InChI:InChI=1/C11H17N2.HI/c1-12-7-3-5-10(9-12)11-6-4-8-13(11)2;/h3,5,7,9,11H,4,6,8H2,1-2H3;1H/q+1;/p-1

Upstream product

• 74-88-4 methyl iodide 
• 54-11-5 nicotin 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 

Relevant academic research and scientific papers

Nanopore Detection of Single-Molecule Binding within a Metallosupramolecular Cage

Guest encapsulation is a fundamental property of coordination cages. However, there is a paucity of methods capable of quantifying the dynamics of guest binding processes. Here, we demonstrate nanopore detection of single-molecule binding within metallosupramolecular cages. Real-time monitoring of the ion current flowing through a transmembrane α-hemolysin nanopore resolved the binding of different guests to both cage enantiomers. This enabled the single-molecule kinetics of guest binding to be quantified, whereas the ordering and durations of events were consistent with a guest-exchange mechanism that does not involve ligand dissociation. In addition to providing a new approach for single-molecule interrogation of dynamic supramolecular processes, this work also establishes that cage complexes which are too large to enter the nanopore can be exploited for detecting small molecules, thus constituting a new class of molecular adapter.

Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring

The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.

Chiral ionic liquids based on nicotine for the chiral recognition of carboxylic acids

The synthesis of enantiopure ionic liquids based on (-)-nicotine is discussed. The desired compounds were prepared in good yields from (-)-nicotine via quaternization of the pyridine ring of (-)-nicotine with MeI and EtBr. After anion metathesis the ionic liquids were investigated as chiral solvating agents and showed a splitting of the signals of Mosher's acid and mandelic acid in the 1H and 19F NMR spectra. In addition to aprotic solvents it was also possible to use methanol in the experiments.

THE SELECTIVITY IN N-ALKYLATION OF NICOTINE.

In preference to pyrrolidine, pyridine moiety of nicotine was alkylated by alkyl halides.This preference seemed to result from the difference of steric hinderance around each nitrogen.The reactivity of pyridine moiety was accelerated by the electronic effect of pyrrolidine.The selective alkylation of pyridine appeared to be available for preparation of artificial antigen of nicotine.

Steric and Conformational Effects in Nicotine Chemistry

The stereoselectivity of iodomethylation of nicotine and seven nicotine analogues having pyridine alkyl groups was determined by using 13C NMR.Alkylation at the pyridine (N) and at the pyrrolidine (N') nitrogens was observed.Two modes of N'-iodomethylation occur, cis and trans to the pyridine ring.N'-Iodomethylation occurs regioselectively cis to the pyridine ring for all compounds examined.The N/N' and N'cis/N'trans ratios for the nicotinoids were evaluated with regard to (1) the orientation of the N'-methyl group in the free base, (2) conformational properties of the pyridine ring with respect to the pyrrolidine ring, and (3) steric hindrance and buttressing effects on the pyridine nitrogen.The Curtin-Hammett principle and the Winstein-Holness equation are used to analyse reactions.