Quinolizidine

Base Information

• Chemical Name: Quinolizidine
• CAS No.: 493-10-7
• Molecular Formula: C9H17N
• Molecular Weight: 139.241
• UNII: S6O58HOW33
• DSSTox Substance ID: DTXSID90964203
• Nikkaji Number: J11.680G
• Wikipedia: Quinolizidine
• Wikidata: Q418837
• Metabolomics Workbench ID: 56691
• Mol file: 493-10-7.mol

Synonyms:Quinolizidine;Quinolizidines

Chemical Property of Quinolizidine

Chemical Property:

• Vapor Pressure: 0.468mmHg at 25°C
• Boiling Point: 193.3°Cat760mmHg
• PKA: 10.57±0.20(Predicted)
• Flash Point: 63.2°C
• PSA: 3.24000
• Density: 0.94g/cm³
• LogP: 1.96270
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 139.136099547
• Heavy Atom Count: 10
• Complexity: 99.3

Purity/Quality:

99% ^*data from raw suppliers

octahydro-2H-Quinolizine 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCCC2C1

Technology Process of Quinolizidine

There total 76 articles about Quinolizidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-azidononanedial (1097909-34-6) → quinolizidine (493-10-7)

Guidance literature:

With 20% palladium hydroxide on carbon; hydrogen; In methanol; at 20 ℃; under 3750.38 Torr; Inert atmosphere; Autoclave;

DOI:10.1021/ol902718q

Reference yield: 93.0%

quinolizidin-4-one (491-40-7) → quinolizidine (493-10-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04199

Reference yield: 85.0%

(S)-1,2,3,6,7,8,9,9a-octahydroquinolizin-4-one (393827-13-9) → quinolizidine (493-10-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux;

DOI:10.1055/s-2008-1067204

upstream raw materials:

2-(4-hydroxybutyl)piperidine

2,3,4,6,7,8-hexahydro-1H-quinolizine

formic acid

quinolizidin-4-one

Downstream raw materials:

2,3,4,6,7,8-hexahydro-1H-quinolizine

quinoline

10-Methyl-chinolizidin

Refernces

An efficient sequential reaction process to polysubstituted indolizidines and quinolizidines and its application to the total synthesis of indolizidine 223A

10.1021/ol047476y

The study presents an efficient sequential reaction process for the synthesis of polysubstituted indolizidines and quinolizidines, which are important structural motifs found in a variety of natural products with biological activities such as neurological and antitumor functions. The process involves the reaction of iodides with δ-chloropropylamines in the presence of potassium carbonate (K2CO3) in acetonitrile (MeCN), resulting in a series of SN2/Michael addition/SN2/SN2 reactions. This method was used to synthesize indolizidine 223A, a specific alkaloid, from 2-ethyl-2-hexenoic acid in 12 linear steps with an overall yield of 14.5%. The chemicals used in the study include iodides 1, δ-chloropropylamines 5, and K2CO3, which serve as reactants and catalysts to facilitate the formation of the target compounds. The purpose of these chemicals is to enable a rapid and stereocontrolled evolution of molecular complexity, which is crucial for the total synthesis of natural products and for diversity-oriented synthesis in drug development and chemical biology.

Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition

10.1021/jo101910r

The study presents a nine-step total synthesis of the quinolizidine alkaloid (+)-Epilupinine with an overall yield of 48%. The key step in this synthesis is the intramolecular nitrile oxide-alkene cycloaddition (INOC), which is used to construct the quinolizidine skeleton. The researchers developed a novel method to efficiently prepare the challenging intermediate (R)-(2-vinylpiperid-1-yl)propanal oxime (13a) from (R)-(2-vinylpiperid-1-yl)propanol (11a) using a two-step process involving Mitsunobu reaction and N-detosylation, avoiding the use of the highly unstable aldehyde intermediate. This method was further generalized to convert various 3-(N,N-dialkylamino)propanols into their corresponding oximes. The final steps of the synthesis involve a Raney nickel-promoted desulfurization to yield the target compound (+)-Epilupinine. The study not only provides a practical and scalable route to this biologically important alkaloid but also offers a new approach for the application of INOC in the total synthesis of other alkaloids.