Pyrrolizidine

Base Information

• Chemical Name: Pyrrolizidine
• CAS No.: 643-20-9
• Molecular Formula: C7H13 N
• Molecular Weight: 111.187
• Hs Code.: 2933990090
• European Community (EC) Number: 613-574-8
• NSC Number: 90874
• UNII: U81KWZ2JKN
• DSSTox Substance ID: DTXSID00214524
• Nikkaji Number: J110.405E
• Wikipedia: Pyrrolizidine
• Wikidata: Q1078442
• Metabolomics Workbench ID: 63589
• Mol file: 643-20-9.mol

Synonyms:PYRROLIZIDINE;643-20-9;Hexahydropyrrolizine;Hexahydro-1H-pyrrolizine;hexahydro-pyrrolizine;1H-Pyrrolizine, hexahydro-;1-Azabicyclo(3.3.0)octane;2,3,5,6,7,8-hexahydro-1H-pyrrolizine;1-Azabicyclo[3.3.0]octane;UNII-U81KWZ2JKN;U81KWZ2JKN;HSDB 4300;MFCD22200264;NSC 90874;NSC-90874;NSC-145060;Hexahydro-1H-pyrrolizine #;PYRROLIZIDINE [HSDB];SCHEMBL35282;CHEBI:64950;DTXSID00214524;NSC90874;1,2,3,4,5,6,7,8-octahydro-pyrrolizine;Q1078442

Chemical Property of Pyrrolizidine

Chemical Property:

• Vapor Pressure: 4.78mmHg at 25°C
• Refractive Index: 1.4731 (estimate)
• Boiling Point: 145.8°C at 760 mmHg
• Flash Point: 34.2°C
• PSA: 3.24000
• Density: 0.97g/cm³
• LogP: 1.18250
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.104799419
• Heavy Atom Count: 8
• Complexity: 80.4

Purity/Quality:

99% ^*data from raw suppliers

Hexahydro-pyrrolizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CC2CCCN2C1
• General Description: Hexahydro-1H-pyrrolizine (also known as pyrrolizidine) is a saturated bicyclic amine structure that serves as a core scaffold for biologically active pyrrolizidine alkaloids. The referenced study highlights its relevance in the synthesis of antiviral and antitumoral agents, demonstrating its utility as an intermediate in alkaloid synthesis through intramolecular nitrone cycloaddition reactions. The research underscores the accessibility of both racemic and enantiopure forms of pyrrolizidine derivatives, emphasizing their potential for further functionalization and asymmetric synthesis.

Technology Process of Pyrrolizidine

There total 38 articles about Pyrrolizidine 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: 95.0%

1-Benzyloxycarbonyl-5-oxoperhydroazocine (80662-83-5) → pyrrolizidine (643-20-9)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In methanol; for 6h; under 760.2 Torr; Ambient temperature;

DOI:10.1021/jo00347a024

Reference yield: 77.0%

1,2,5,6,7,8-hexahydro-3H-pyrrolizin-3-one (32548-24-6) → pyrrolizidine (643-20-9)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1055/s-2007-990946

Reference yield: 55.0%

2-(3-Oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester (209409-40-5) → pyrrolizidine (643-20-9)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.5h; Heating;

DOI:10.1002/jhet.5570350219

upstream raw materials:

tetrahydro-pyrrolizin-3,5-dione

1,4,7-tribromo-heptane

4-hydroxyimino-heptanedioic acid diethyl ester

dimethyl 4-nitro-1,7-heptanedioate

Downstream raw materials:

1-(2-Hydroxyethyl)pyrrolizidinium bromide α-phenylcyclopentaneacetate

pyrrolizidinium picrate

Refernces

Intramolecular cycloadditions of nittones derived from 1-allyl-2- pyrrolecarbaldehyde as a route to racemic and enantiopure pyrrolizidines and indolizidines

10.1021/jo9810415

The research focuses on the synthesis of pyrrolizidines and indolizidines, which are structurally related to biologically active alkaloids, using a novel intramolecular nitrone cycloaddition strategy. The purpose of this study was to develop a method for synthesizing these compounds, which possess a wide range of potent biological activities and are considered promising antiviral and antitumoral agents. The researchers successfully synthesized the target molecules in both racemic and enantiopure forms, demonstrating the potential of nitrones derived from 1-allyl-2-pyrrolecarbaldehyde as useful intermediates in alkaloid synthesis. The conclusions highlighted the accessibility of both racemic and enantiopure molecules and suggested future directions for the synthesis of more functionalized structures and improving the degree of asymmetric induction. Key chemicals used in the process included 1-allyl-2-pyrrolecarbaldehyde, benzylhydroxylamine, (R)-N-(1-phenylethyl)hydroxylamine, and various catalysts and solvents such as Pd/C, toluene, and methanol.