202187-27-7

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-amino-, (1S,2S,3R,4R)- (9CI)
• Synonyms: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-amino-, (1S,2S,3R,4R)- (9CI);(1S,2S,3R,4R)-(+)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS NO: 202187-27-7
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.17844
• Product Categories: CARBOXYLICACID;CYCLOPENTANE
• Mol File: 202187-27-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 309.2°C at 760 mmHg
• Flash Point: 140.8°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 0.000145mmHg at 25°C
• Refractive Index: 1.583
• PKA: 3.66±0.20(Predicted)
• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-amino-, (1S,2S,3R,4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-amino-, (1S,2S,3R,4R)- (9CI)(202187-27-7)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-amino-, (1S,2S,3R,4R)- (9CI)(202187-27-7)

Safety Data

• Hazardous Substances Data: 202187-27-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11NO2/c9-7-5-2-1-4(3-5)6(7)8(10)11/h1-2,4-7H,3,9H2,(H,10,11)/t4-,5+,6+,7-/m1/s1

Upstream product

• 5433-80-7 cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide 
• 21715-90-2 endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide 
• 14735-70-7 3-azatricyclo[4.2,1.0.(2,5)]non-7-en-4-one 
• 14735-70-7 diexo-3-Aza-4-oxotricyclo<4.2.1.0^2,5>non-7-ene 
• 105786-36-5 ethyl 3-exo-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 790187-08-5 ethyl (1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 342419-21-0 ethyl (1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 151312-22-0 triplet 1,4-norbornene diradical 

Downstream Products

• 104308-56-7 (1S,2R,3S,4R)-3-(3-p-Tolyl-thioureido)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 104308-56-7 (1R,2R,3S,4S)-3-(3-p-Tolyl-thioureido)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 104308-61-4 (1S,2R,3S,4R)-3-[3-(4-Chloro-phenyl)-thioureido]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 104308-61-4 (1R,2R,3S,4S)-3-[3-(4-Chloro-phenyl)-thioureido]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 1242184-48-0 (1SR,2RS,3SR,4RS)-3-tert-butoxycarbonylaminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 1242184-48-0 C₁₃H₁₉NO₄ 
• 887908-99-8 (1S,2S,3R,4R)-3-exo-N-^tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid 
• 1242184-46-8 C₁₃H₁₉NO₄ 
• 95630-76-5 ethyl 2-endo-aminobicyclo<2.2.1>heptane-1-endo-carboxylate hydrochloride 
• 104308-55-6 (1S,2S,3R,4R)-3-(3-Phenyl-thioureido)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 104308-55-6 (1R,2S,3R,4S)-3-(3-Phenyl-thioureido)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 87768-94-3 3-exo-Hydroxymethylbicyclo<2.2.1>hept-5-enyl-2-exo-amine 
• 87768-94-3 diendo-3-hydroxymethylbicyclo[2.2.1]hept-5-en-2-ylamine 
• 104770-18-5 ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride 

Relevant articles and documents

Synthesis of novel N-heterocyclic compounds containing 1,2,3-triazole ring system via domino, “click” and RDA reactions

An uncomplicated, high-yielding synthetic route has been developed to constitute complicated heterocycles, applying domino, click and retro-Diels–Alder (RDA) reaction sequences. Starting from 2-aminocarboxamides, a new set of isoindolo[2,1-a]quinazolinones was synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by1H and13C Nuclear Magnetic Resonance (NMR) methods.

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

A new access route to functionalized cispentacins from norbornene β-amino acids

An efficient and simple new stereocontrolled access route to novel disubstituted cispentacin derivatives with multiple stereogenic centers from norbornene β-lactam has been developed. The synthesis involves olefinic bond functionalization by dihydroxylation followed by oxidative ring cleavage and transformation of the dialdehyde intermediate through a Wittig reaction. Copyright