314280-30-3

Basic information

• Product Name: 3-Pyridinemethanamine,alpha-2-propenyl-,(alphaS)-(9CI)
• Synonyms: 3-Pyridinemethanamine,alpha-2-propenyl-,(alphaS)-(9CI)
• CAS NO: 314280-30-3
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.21
• Product Categories: PYRIDINE
• Mol File: 314280-30-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pyridinemethanamine,alpha-2-propenyl-,(alphaS)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinemethanamine,alpha-2-propenyl-,(alphaS)-(9CI)(314280-30-3)
• EPA Substance Registry System: 3-Pyridinemethanamine,alpha-2-propenyl-,(alphaS)-(9CI)(314280-30-3)

Safety Data

• Hazardous Substances Data: 314280-30-3(Hazardous Substances Data)

Upstream product

• 949021-12-9 (S)-2-[(S)-1-(3-pyridyl)-3-butenylamino]-3-methyl-1-butanol 
• 314280-28-9 (R)-1-(pyridin-3-yl)but-3-en-1-ol 
• 108-21-4 Isopropyl acetate 
• 141-78-6 ethyl acetate 
• 151914-34-0 2,2,2-trifluoroethyl 1-chloroacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 406-95-1 2,2,2-trifluoroethyl acetate 
• 500-22-1 3-pyridinecarboxaldehyde 
• 154228-37-2 methyl N-[1(S)-(3-pyridyl)-3-buten-1-yl]-(S)-valinate 
• 949020-93-3 (S)-3-Methyl-2-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-butyric acid methyl ester 
• 910545-65-2 (1R,3R,4S)-3-allyl-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 314280-29-0 (S)-3-(1-azido-but-3-enyl)pyridine 
• 372519-16-9 (R)-methanesulfonic acid 1-pyridin-3-yl-but-3-enyl ester 

Downstream Products

• 314280-31-4 (S)-(1-pyridin-3-yl-but-3-enyl)-carbamic acid benzyl ester 

Relevant articles and documents

Lipase catalysis in the preparation of 3-(1-amino-3-butenyl)pyridine enantiomers

The kinetic resolution of 1-(3-pyridyl)buten-3-ylamine with activated and non-activated acyl donors and Burkholderia cepacia lipase (lipase PS-D) under dry conditions has been studied. The N-acylation in isopropyl acetate (E >100) and the acidic hydrolysi

Asymmetric synthesis of δ-substituted α,β-unsaturated δ-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines

(Chemical Equation Presented) Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl

Enantioselective transfer aminoallylation: Synthesis of optically active homoallylic primary amines

A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with hi

Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco

An enantiomeric synthesis of six piperidine and pyrrolidine alkaloids, (S)-nornicotine 1, (S)-nicotine 2, (S)-anatabine 3, (S)-N-methylanatabine 4, (S)-anabasine 5, and (S)-N-methylanabasine 6, known as natural products in tobacco, was established from a common chiral homoallylic (S)-3-(1-azidobut-3-enyl)-pyridine 15. An intramolecular hydroboration-cycloalkylation of the homoallylic azide intermediate 15 served as the key step in the pyrrolidine ring formation. A ring closing metathesis reaction (RCM) of a diethylenic amine intermediate (S)-allyl-(1-pyridin-3-yl-but-3-enyl)-carbamic acid benzyl ester 20 served as the key step in the piperidine ring formation. From the commercially available 3-pyridinecarboxaldehyde 13, a short and convenient enantiomeric synthesis of tobacco alkaloids is described: (S)-nornicotine I (5 steps, with an overall yield of 70%), (S)-hicotine 2 (6 steps, 65%), (S)-anatabine 3 (8 steps, 30%), (S)-N-methylanatabine 4 (8 steps, 25%), (S)-anabasine 5 (8 steps, 35%), and (S)-N-methylanabasine 6 (8 steps, 25%).

Total synthesis of (S)-anabasine and (S)-anatabine

A chiral synthesis of (S)-anabasine and (S)-anatabine from 3-pyridinecarboxaldehyde, via a ring closing metathesis reaction (RCM) as the key step, is reported in 8 steps for both products with overall yields of 35% and 30%, respectively.