493-10-7

Basic information

• Product Name: Quinolizidine
• Synonyms: 1,3,4,6,7,8,9,9a-Octahydro-2H-quinolizine;Norlupinane;Octahydro-2H-quinolizine;Octahydro-4H-quinolizine;Quinolizidine
• CAS NO: 493-10-7
• Molecular Formula: C₉H₁₇N
• Molecular Weight: 139.238
• Mol File: 493-10-7.mol

Chemical Properties

• Boiling Point: 193.3°Cat760mmHg
• Flash Point: 63.2°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.468mmHg at 25°C
• Refractive Index: 1.503
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: Quinolizidine(CAS DataBase Reference)
• NIST Chemistry Reference: Quinolizidine(493-10-7)
• EPA Substance Registry System: Quinolizidine(493-10-7)

Safety Data

• Hazardous Substances Data: 493-10-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Octahydro-4H-quinolizine is used as an active pharmaceutical ingredient for its potential therapeutic properties. Its unique chemical structure allows it to interact with specific biological targets, making it a valuable compound in the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, Octahydro-4H-quinolizine is used as a key intermediate in the synthesis of various complex organic molecules. Its versatile structure enables it to be modified and functionalized, leading to the creation of a wide range of chemical products.
Used in Material Science:
Octahydro-4H-quinolizine is utilized as a building block in the development of novel materials with specific properties. Its incorporation into polymers and other materials can enhance their performance, making them suitable for various applications, such as in electronics, coatings, and adhesives.
Used in Agrochemical Industry:
Octahydro-4H-quinolizine is employed as a component in the formulation of agrochemicals, such as pesticides and herbicides. Its ability to interact with specific biological targets makes it a valuable tool in the development of more effective and targeted agrochemical products.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 939, 1984 DOI: 10.1016/S0040-4039(01)80067-8

InChI:InChI=1/C9H17N/c1-3-7-10-8-4-2-6-9(10)5-1/h9H,1-8H2

Upstream product

• 90726-50-4 2-(4-hydroxybutyl)piperidine 
• 6391-47-5 2,3,4,6,7,8-hexahydro-1H-quinolizine 
• 64-18-6 formic acid 
• 491-40-7 quinolizidin-4-one 
• 114426-09-4 4-(6-oxo-1,4,5,6-tetrahydro-[2]pyridyl)-butyric acid amide 
• 60-29-7 diethyl ether 
• 1068-56-0 isopropylmagnesium iodide 
• 99064-22-9 1,5,9-tribromo-nonane 
• 64-17-5 ethanol 
• 590-29-4 potassium formate 
• 408326-66-9 5-bromo-1-(4-bromo-butyl)-pentylamine 
• 84199-92-8 diethyl 2-(2-pyridyl)ethylmalonate 
• 4396-27-4 nonamethyleneimine 
• 10297-05-9 1-chloro 4-iodobutane 

Downstream Products

• 6391-47-5 2,3,4,6,7,8-hexahydro-1H-quinolizine 
• 91-22-5 quinoline 
• 4939-43-9 10-Methyl-chinolizidin 

Relevant articles and documents

Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids

A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.

Synthesis of indolizidine, pyrrolizidine and quinolizidine ring systems by proline-catalyzed sequential α-amination and HWE olefination of an aldehyde

A general procedure for the synthesis of azabicyclic ring systems viz. indolizidine, pyrrolizidine and quinolizidine has been developed utilizing proline-catalyzed sequential α-amination and Horner-Wadsworth-Emmons (HWE) olefination of an aldehyde as the key step. This method can be further extended to the synthesis of various biologically active natural products containing azabicyclic ring systems.

Multialkylation of aqueous ammonia with alcohols catalyzed by water-soluble Cp*Ir-ammine complexes

Novel water-soluble Cp*Ir-ammine complexes have been synthesized, and a new and highly atom-economical system for the synthesis of organic amines using aqueous ammonia as a nitrogen source has been developed. With a water-soluble and air-stable Cp*Ir-ammine catalyst, [Cp*Ir(NH 3)3][I]2, a variety of tertiary and secondary amines were synthesized by the multialkylation of aqueous ammonia with theoretical equivalents of primary and secondary alcohols. The catalyst could be recycled by a facile procedure maintaining high activity. A one-flask synthesis of quinolizidine starting with 1,5,9-nonanetriol was also demonstrated. This new catalytic system would provide a practical and environmentally benign methodology for the synthesis of various organic amines.

Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation

[Chemical equation presented] Short and efficient access to (+)-lupinine and (+)-epiquinamide by means of an unprecedented double hydroformylation of a bis-homoallylic azide followed by a tandem catalytic hydrogenatlon/reductive bis-amination is reported.

ELECTROLYTE, ELECTROLYTIC SOLUTION, AND ELECTROCHEMICAL DEVICE USING THE SAME

Disclosed herein is an electrolyte having excellent long-term reliability, a high withstanding voltage (a wide potential window), and high conductivity. The electrolyte contains a quaternary ammonium salt represented by the following general formula (1): wherein R1 represents a hydrocarbon group; R2 represents a hydrocarbon group, a hydrogen atom, or a halogen atom; R3 to R14 each represent an alkyl group, a fluoroalkyl group, a hydrogen atom or a halogen atom, C and C* each represent a carbon atom, N represents a nitrogen atom; h, i, j, x, y, and z are each an integer of 0 to 6, (h+x) is an integer of 0 to 6, (i+y) and (j+z) are each an integer of 1 to 6; and X? represents a counter anion having a HOMO energy of ?0.60 to ?0.20 a.u. as determined by the first-principle calculation on molecular orbital of the counter anion.

Strategy for the assembly of chiral bicyclic lactams: A concise synthetic route to (-)-coniceine

A concise asymmetric synthesis of chiral bicyclic lactams combining a highly stereoselective 1,2-addition on SAMP hydrazones with a ring closure metathesis has been achieved. The synthetic utility of this approach has been emphasized by the total synthesis of (-)-coniceine in high enantiomeric excess. Georg Thieme Verlag Stuttgart.

Novel synthesis of indolizidines and quinolizidines

A very short synthesis of indolizidines, quinolizidines and some higher homologues was developed by alkylation of 2-methyl-1-pyrroline or 6-methyl-2,3,4,5-tetrahydropyridine with 1,3- or 1,4-dihaloalkanes, followed by reduction of the intermediate iminium salts, resulting in the desired 1-azabicyclo[m.n.0]alkanes in good yields.

The stereochemistry of the reduction of cyclic enaminones

The stereo- and regiochemistry of di-, tri-, and tetracyclic enaminones upon catalytic hydrogenation on Pd and Pt catalysts seems to be mainly a function of the catalyst and the medium. The highest stereoselectivity was observed for multiflorine on Pd/C in which 99% of equatorial alcohol were formed in this case, the formation of alcohols proceeds via a ketonic intermediate. On platinum, irrespective of the solvent used (EtOH, H2O, AcOH, HCl), the hydrogenation reaction proceeds through ketonic (piperidone system) and dehydro (pyridone system) intermediates. In EtOH or H2O solution, the dehydro product remains unchanged, whereas the ketonic intermediate is reduced to a mixture of epimeric alcohols. In HCl and acetic acid, both intermediates are hydrogenolyzed to a product with a methylene group, but the ketonic one is additionally reduced to a mixture of epimeric alcohols. Reductions with complex metal hydrides provide mixtures of epimeric alcohols with a predominance of equatorial orientation. The structures of products were determined by NMR spectroscopy and/or by GC-MS analysis.

Efficient syntheses of functionalized piperidines through extremely regioselective Rh-catalyzed cyclohydrocarbonylation of amido-ω,ω'-dienes

The highly regioselective cyclohydrocarbonylation of 4-amido-1,6- heptadienes catalyzed by Rh-BIPHEPHOS complex gives functionalized piperidines quantitatively, which serve as versatile intermediates for the syntheses of a variety of piperidine and quinolizidine alkaloids. Reaction of 3-Boc-amino-1,5-hexadiene affords the corresponding dehydropiperidine- aldehyde exclusively via site and regioselective hydroformylation. Possible mechanisms for these reactions are proposed.

Introduction of alkyl groups at the α-positions of pyrrolidines and piperidines: Synthesis of (±)-coniine

The conversion of lactams to α-alkylated cyclic amines is described. Reactions of α-ethoxyurethanes with trimethylsilyl cyanide in the presence of Lewis acid afford the corresponding α-cyanourethanes, which, via carbanion, are alkylated to α-alkyl-α-cyanourethanes in moderate to high yields. Syntheses of (±)-coniine and trans-quinolizidine are carried out as model experiments for dealkoxycarbonylation and decyanation of 2-alkyl-1-alkoxycarbonyl-2-cyanopiperidines.