51463-41-3

Basic information

• Product Name: 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE
• Synonyms: 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE
• CAS NO: 51463-41-3
• Molecular Formula: C₇H₁₁N
• Molecular Weight: 109.16894
• Mol File: 51463-41-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE(51463-41-3)
• EPA Substance Registry System: 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE(51463-41-3)

Safety Data

• Hazardous Substances Data: 51463-41-3(Hazardous Substances Data)

Usage

General Description

2,3,5,7A-Tetrahydro-1H-pyrrolizine, also known as THP, is a heterocyclic compound with the molecular formula C8H15N. It is a clear, colorless liquid with a faint, amine-like odor. THP is used in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals, as a building block for creating complex molecules. It can also be found in certain natural products, such as alkaloids. THP has been studied for its potential as a building block in the synthesis of bioactive compounds, and it has shown promise in a variety of medicinal applications, such as anti-inflammatory and anti-cancer properties. However, it is important to handle THP with caution, as it is considered to be toxic and can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 7223-42-9 1-(prop-2-yn-1-yl)pyrrolidine 
• 233595-58-9 2-(1,2-propadienyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 

Downstream Products

• 78719-89-8 1α,2α-epoxypyrrolizidine 
• 78719-89-8 1β,2β-epoxypyrrolizidine 
• 14051-10-6 1α,1'α:2β,2'β-(bisdithiodipyrrolizidine) 
• 78719-92-3 1β-(2α-thiobenzoylpyrrolizidine)-methanesulfonate 
• 78719-93-4 1β-hydroxy-2α-thiobenzylpyrrolizidine 
• 78719-93-4 1α-hydroxy-2β-thiobenzylpyrrolizidine 
• 78719-91-2 1β-hydroxy-2α-thiobenzylpyrrolizidine 
• 78719-91-2 2β-hydroxy-1α-thiobenzylpyrrolizidine 
• 78719-95-6 1α-acetoxy-2β-thiobenzylpyrrolizidine 
• 78719-95-6 1β-acetoxy-2α-thiobenzylpyrrolizidine 
• 78719-98-9 C₂₈H₃₆N₂S₄ 
• 78719-98-9 1α,1'α-dithio-2β,2'β-dithiobenzylpyrrolizidine 

Relevant articles and documents

Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates: Synthetic route to α-amino allenes and Δ3-pyrrolines

(Chemical Equation Presented) Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)-alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2′ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2′ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.

Acetylenes as Potential Antarafacial Components in Concerted Reactions. Formation of Pyrroles from Thermolyses of Propargylamines, of a Dihydrofuran from a Propargylic Ether, and of an Ethylidenepyrrolidine from a β-Amino Acetylene

A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in processes.The cyclization competes with the normally favored acetylenic retro-ene reaction.Propargylic amines, without substituents whose presence would hinder a tight cyclic transition state, yield intermediate pyrrolines whose subsequent hydrogen elimination affords pyrroles in small amounts.The same process in 2-ethynyltetrahydropyran affords 8-oxabicyclooctane in 35percent yield.A related thermal reaction of N-methyl-3-hexyn-1-amine provides a quantitative transformation to N-methyl-2-ethylidenepyrrolidine in a nominal s + 2a + 2s + 2s> Moebius process, wherein the acetylenic unit is the antarafacial component.Evidence for concertedness in these reactions is discussed.