Octahydroindolizine

Base Information

• Chemical Name: Octahydroindolizine
• CAS No.: 13618-93-4
• Molecular Formula: C8H15 N
• Molecular Weight: 125.214
• European Community (EC) Number: 237-103-7
• UNII: 4FG58K748F
• DSSTox Substance ID: DTXSID40929286
• Nikkaji Number: J14.076G
• Wikipedia: Indolizidine
• Wikidata: Q33015
• Mol file: 13618-93-4.mol

Synonyms:OCTAHYDROINDOLIZINE;Indolizidine;13618-93-4;Indolizine, octahydro-;.delta.-Coniceine;OCTAHYDRO-INDOLIZINE;1-Azabicyclo[4.3.0]nonane;1,2,3,5,6,7,8,8a-octahydroindolizine;UNII-4FG58K748F;4FG58K748F;EINECS 237-103-7;1-AZABICYCLO(4.3.0)NONANE;delta-Coniceine;Octahydroindolizine #;1-azabicyclo[4,3,0]nonane;SCHEMBL339598;DTXSID40929286;(+/-)-OCTAHYDROINDOLIZINE;.DELTA.-(+/-)-CONICEIN;(+/-)-.DELTA.-CONICEINE;MFCD02066234;AKOS005256379;OCTAHYDROINDOLIZINE, (+/-)-;AS-38195;EN300-61515;2,3,4,5,6,7,8,8a-octahydro-1H-indolizine;Q33015;J-006820;Z966989444

Chemical Property of Octahydroindolizine

Chemical Property:

• Vapor Pressure: 1.33mmHg at 25°C
• Refractive Index: 1.4748 (estimate)
• Boiling Point: 172.5°Cat760mmHg
• PKA: 10.57±0.20(Predicted)
• Flash Point: 50.6°C
• PSA: 3.24000
• Density: 0.95g/cm³
• LogP: 1.57260
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 125.120449483
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Octahydroindolizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCC2C1

Technology Process of Octahydroindolizine

There total 114 articles about Octahydroindolizine 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%

indolizidin-3-one (2740-00-3,71779-55-0) → indolizidine (13618-93-4)

Guidance literature:

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

DOI:10.1021/acs.orglett.9b04199

Reference yield: 99.0%

hexahydroindolizin-5(1H)-one (32537-55-6) → indolizidine (13618-93-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 15h; Heating;

DOI:10.1021/jo00281a022

Reference yield: 83.0%

N-(carbobenzyloxy)-5-azacyclononanone (80249-00-9) → indolizidine (13618-93-4)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In methanol; for 24h; under 2662.7 Torr;

DOI:10.1021/jo00347a024

upstream raw materials:

indolizine

2-(2-Cyanoethyl)pyridine

3-(pyridin-2-yl)-propanol

3-(2-pyridyl)propanal diethylacetal

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.

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.