84235-37-0

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester, (1R-exo)- (9CI)
• Synonyms: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester, (1R-exo)- (9CI)
• CAS NO: 84235-37-0
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19038
• Product Categories: CARBOXYLICESTER
• Mol File: 84235-37-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester, (1R-exo)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester, (1R-exo)- (9CI)(84235-37-0)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester, (1R-exo)- (9CI)(84235-37-0)

Safety Data

• Hazardous Substances Data: 84235-37-0(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 120-74-1 (1R,2R)-5-norbornene-2-carboxylic acid 
• 120-74-1 (1R,2S)-5-norbornene-2-carboxylic acid 
• 136520-58-6 methyl (5R,6R)-6-endo-formylbicyclo<2.2.1>hept-2-eno-5-exo-carboxylate 
• 136520-59-7 methyl (5R,6R)-5-exo-formylbicyclo<2.2.1>hept-2-eno-6-endo-carboxylate 
• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 67-56-1 methanol 
• 934-30-5 5-norbornene-endo-2-carboxylic acid 

Downstream Products

• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 344585-18-8 (1R,2R,4S)-2-Isocyanato-bicyclo[2.2.1]heptane 

Relevant articles and documents

Novel Potassium-Channel Openers: Preparation and Pharmacological Evaluation of Racemic and Optically Active N-(6-Amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine Derivatives

The previous paper reported on the synthesis and pharmacological evaluation of N-(6-amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine derivatives, from among which three compounds were selected as potent potassium-channel openers. In the present study, selected compounds were tested for antagonism of potassium-induced contraction of rat aorta, hypotensive activity in normotensive rats, and diuretic activity in spontaneously hypertensive rats. This led to further evaluation of compound (+/-)-10 and selection of (+)-N-(6-amino-3-pyridyl)-N'-hept-2-yl>-N"-cyanoguanidine ((+)-10) (AL0670) for development as an antihypertensive agent. Although AL0670 is regarded as a pinacidil-type K+-channel opener, it showed different pharmacological and conformational profiles from pinacidil.

Transformations of unsaturated acyclic sugars into enantiomerically pure norbornene derivatives

The C7 acyclic unsaturated-sugar ester 1, derived from L-arabinose, and its enantiomer serve as convenient dieneophiles for chirality transfer for synthesis of optically pure carbocyclic derivatives through cycloaddition reactions.Reaction of 1 with cyclopentadiene may be controlled to give preparative access to the 5,6-disubstituted norbornene adducts 4a, 5a and 7a, according to the conditions used.The distribution of the four possible isomeric products from this cycloaddition was quantitated, and the effect of substitutional variation on the precursor dienophile 1 was also examined.Adducts 4a and 5a were transformed into such substituted carbocycles of known absolute configuration as the methyl esters (11 and 12) of norbornene (bicyclohept-2-ene)-6-carboxylic acid and nortricyclane (tricyclo2,6>heptane)-3-carboxylic acid in optically pure form, specifically through decarbonylation reactions using RhCl(PPh3)3 (Wilkinson's complex) and Cl.The optical purity of 12 was established by the use of a chiral lanthanide shift-reagent.