131102-02-8

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-(acetylamino)-, (1R-exo)- (9CI)
• Synonyms: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-(acetylamino)-, (1R-exo)- (9CI)
• CAS NO: 131102-02-8
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.21512
• Product Categories: AMINOACID
• Mol File: 131102-02-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-(acetylamino)-, (1R-exo)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-(acetylamino)-, (1R-exo)- (9CI)(131102-02-8)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-(acetylamino)-, (1R-exo)- (9CI)(131102-02-8)

Safety Data

• Hazardous Substances Data: 131102-02-8(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 72431-82-4 methyl 2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 72431-82-4 methyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 542-92-7 cyclopenta-1,3-diene 
• 131053-11-7 (-)-menthyl N-acetyl-α,β-dehydroalaninate 
• 136205-74-8 (1R,2S,4R)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether 
• 131101-99-0 (1R,2S)-(-)-menthyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 5429-56-1 N-Acetamidoacrylic acid 
• 131053-12-8 (-)-menthyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 

Downstream Products

• 131454-99-4 2-endo-Acetamido-2-exo-phenylethynylnorbornene 
• 131454-99-4 N-((1R,2S,4R)-2-Phenylethynyl-bicyclo[2.2.1]hept-5-en-2-yl)-acetamide 
• 132968-87-7 2-endo-Acetamido-2-exo-benzylthionorbornane 
• 132968-87-7 2-exo-Acetamido-2-endo-benzylthionorbornane 
• 131454-95-0 2-exo-Acetamido-2-endo-phenylthionorbornene 
• 131454-95-0 2-endo-Acetamido-2-exo-phenylthionorbornene 
• 131454-98-3 2-endo-Acetamido-2-exo-phenylaminonorbornene 
• 35719-58-5 2-exo-aminobicyclo<2.2.1>heptane-2-endo-carboxylic acid 
• 34270-17-2 (1R,2S,4S)-2-aminobicyclo<2.2.1>heptane-2-carboxylic acid 
• 34270-16-1 2-endo-aminobicyclo<2.2.1>heptane-2-exo-carboxylic acid 
• 35719-57-4 (-)-(1R,2R,4S)-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid 

Relevant articles and documents

1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems

Enantiopure constrained 1-aminocyclopentane-1,2,4-tricarboxylic acids containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carboxylic groups in position two and four cis-oriented to each other and trans with respect to 1-carboxylic group and all cis-oriented carboxylic groups, respectively. A biochemical screening of activity of the above amino acids was investigated on glutamate and 5-HT receptors to find a possible metabotropic agonist, acting on the serotoninergic system.

The Diels-Alder reactions of polymer bound dehydroalanine derivatives

The synthesis and Diels-Alder cycloadditions of a number of polymer bound dehydroalanine derivatives are described. The studies compare methodologies for accessing polymer bound dehydroalanines and establish the versatility and efficiency of solid phase Diels-Alder reactions in the synthesis of carbocyclic amino acids. These studies nicely complement the growing repertoire of methodologies for the functionalisation of amino acid derivatives.

ASYMMETRIC SYNTHESIS OF 2-EXO-AMINONORBORNANE-2-ENDO-CARBOXYLIC ACID DERIVATIVES

The Diels-Alder reaction of cyclopentadiene with N-acetyl-α,β-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position.So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-α,β-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.