517892-17-0

Usage

InChI:InChI=1/C16H18O3/c1-9-2-4-10(5-3-9)15(17)13-11-6-7-12(8-11)14(13)16(18)19/h2-5,11-14H,6-8H2,1H3,(H,18,19)/t11-,12+,13+,14+/m1/s1

Upstream product

• 17812-27-0 cis-5-norbornene-endo-2,3-dicarboxylic anhydride 
• 517892-17-0 diendo-3-p-toluoylbicyclo[2.2.1]heptane-2-carboxylic acid 
• 2746-19-2 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 108-88-3 toluene 
• 14166-28-0 exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 
• 517892-17-0 3-exo-p-toluoylbicyclo[2.2.1]heptan-2-exo-carboxylic acid 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 

Relevant academic research and scientific papers

Preparation and structure of di-exo-condensed norbornane heterocycles

Cyclization of di-exo-aroylnorbornanecarboxylic acid with bidentate nucleophiles (hydrazine, o-phenylenediamine, o-aminophenol, alkylenediamines, and amino alcohols) yielded heterotri-, tetra-, and pentacycles. Their structures were established by means o

Isomerization and application of aroylnorbornene-carboxylic acids for stereoselective preparation of heterocycles

When boiled in acidic or basic solution, diendo-3-aroylbicyclo[2.2.1]heptane-2-carboxylic acids (1 and 1a) isomerize to exo-3-aroylbicyclo[2.2.1]heptane-endo-2-carboxylic acids (2 and 2a). Similar endo→exo and even exo→endo isomerization of the aroyl group occurred when the Diels-Alder product containing a mixture of 3-exo-p-toluoylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid (4) and 3-endo-p-toluoylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (5) was reacted with bifunctional reagents: o-aminothiophenol, 3-amino-1-propanol, 1,4-diaminobutane or diexo-3-hydroxymethylbicyclo[2.2.1]heptane-2-amine. All the reactions yielded mixtures of norbomene diendo- and diexo-fused heterocycles (6) and (7, 8 and 10, 9 and 11, or 12 and 13), which were separated and whose structures were established by means of IR, 1H- and 13C-NMR spectroscopy, with DIFFNOE, 2D-COSY, DEPT, HMQC and HMBC measurements.

Preparation and Steric Structure of 3(2H)-Pyridazinones and 1,2-Oxazin-6-ones Fused with Three- to Six-membered Saturated Carbocycles or Norbornane Skeleton

Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and -cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cycloheptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed 3(2H)-pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10.With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14.Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24.From the stereoisomeric hexahydro-1(3H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6.On reduction, 16b yield the 2-methyloctahydroanthracene 22.The structures of the compounds were proved by 1H and 13C NMR spectroscopy, making use of NOE, DEPT, and CH-COSY techniques. - Keywords: Cycloalkanes; Heterocycles; Friedel-Crafts acylation; Isomerization; Methyloctahydroanthracen-9-ones; Reduction; LAH/AlCl3.