215674-16-1

Basic information

• Product Name: 2-Azabicyclo[2.2.1]heptane-3-methanol, 2-[(1S)-1-phenylethyl]-, (1S,3R,4R)-
• CAS NO: 215674-16-1
• Molecular Formula: C15H21NO
• Molecular Weight: 231.338
• Mol File: 215674-16-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-Azabicyclo[2.2.1]heptane-3-methanol, 2-[(1S)-1-phenylethyl]-, (1S,3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[2.2.1]heptane-3-methanol, 2-[(1S)-1-phenylethyl]-, (1S,3R,4R)-(215674-16-1)
• EPA Substance Registry System: 2-Azabicyclo[2.2.1]heptane-3-methanol, 2-[(1S)-1-phenylethyl]-, (1S,3R,4R)-(215674-16-1)

Safety Data

• Hazardous Substances Data: 215674-16-1(Hazardous Substances Data)

Upstream product

• 37662-06-9 ethyl <(S)-1-phenylethyl>iminoethanoate 
• 223505-12-2 (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>hept-5-ene-3-carboxylic acid ethyl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 499137-87-0 (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carbaldehyde 
• 223473-32-3 (1S,3R,4R)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 1394910-33-8 (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-phenylselanyl-2-azabicyclo[3.2.1]octane 
• 1394910-39-4 (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-ethoxy-2-azabicyclo[3.2.1]octane 
• 1394910-45-2 (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-(4-nitrobenzoyloxy)methyl-2-azabicyclo[2.2.1]heptane 
• 1394910-35-0 (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-azido-2-azabicyclo[3.2.1]octane 
• 1394910-37-2 (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-chloro-2-azabicyclo[3.2.1]octane 
• 1394910-40-7 (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-amino-2-azabicyclo[3.2.1]octane 
• 215674-17-2 (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde 
• 215674-19-4 (1S,3R,4R)-3-(N-piperidinyl)methyl-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane 
• 215674-18-3 (1S,3R,4R)-3-(N-pyrrolidinyl)methyl-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane 
• 215674-22-9 (1S,3R,4R)-3-pyrrolidin-1-ylmethyl-2-azabicyclo[2.2.1]heptane 

Relevant articles and documents

Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton

A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels–Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by [Formula presented] fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases.

endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction

We report the synthesis and preliminary evaluation of (1S,2S,4R)-7,7-dimethyl-1-phenylbicyclo[2.2.1]heptan-2-ol 1a, which was obtained in 3 steps from inexpensive starting materials, as a chiral auxiliary. The potential for asymmetric induction was investigated by carrying out aza-Diels-Alder reactions with cyclopentadiene and imine derivatives of 1a from (R)-(+)-1-phenylethylamine, (S)-(?)-1-phenylethylamine and benzylamine. The results showed marked exo selectivity and good diastereoisomeric excess when 1a was combined with (R)-(+)-1-phenylethylamine. These results are comparable with those reported using (?)-8-phenylmenthol, suggesting that 1a can represent an economically viable alternative to current chiral auxiliaries.

An enantiopure diselenide based on a chiral bicyclic backbone—synthesis and configuration assignment

An enantiomerically pure diselenide containing two chiral bicyclic subunits was prepared from the respective halides. The stereochemical outcome of the reaction was established via NMR spectroscopy and X-ray diffraction measurements.