(±)-trans-3-Benzoylbicyclo[2.2.2]octane-2-carboxylic acid
نویسندگان
چکیده
The title keto acid, C(16)H(18)O(3), displays significant twisting of all three ethyl-ene bridges in its bicyclo-[2.2.2]octane structure owing to steric inter-actions; the bridgehead-to-bridgehead torsion angles are 13.14 (12), 13.14 (13) and 9.37 (13)°. The compound crystallizes as centrosymmetric carboxyl dimers [O⋯O = 2.6513 (12) Å and O-H⋯O = 178°], which have two orientations within the cell and contain no significant carboxyl disorder.
منابع مشابه
Syntheses of four enantiomers of 2,3-diendo- and 3-endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic acid and their saturated analogues.
Ethyl 2,3-diendo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylate ((±)-1) was resolved with O,O'-dibenzoyltartaric acid via diastereomeric salt formation. The efficient synthesis of the enantiomers of 2,3-diendo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid ((+)-7 and (-)-7), 3-endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic acid ((+)-5 and (-)-5), cis- and trans-3-aminobicyclo[2.2.2]octane-2...
متن کاملSynthesis and transformations of di-endo-3-aminobicyclo-[2.2.2]oct-5-ene-2-carboxylic acid derivatives.
all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and all-endo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or g-lactone intermediates by the stereoselective functionalization of an N-protected derivative of endo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid (2). Ring closure of b-amino ester 4 resulted in tricyclic pyrimidi...
متن کاملUse of molecular electrostatic potential for quantitative assessment of inductive effect.
Density functional theory computations at the B3LYP/6-31G(d,p) level have been carried out for three types of model compounds, viz. (i) 4-substituted bicyclo[2.2.2]octane carboxylic acids, (ii) anions of 4-substituted bicyclo[2.2.2]octane carboxylic acids and (iii) 4-substituted quinuclidines where the substituents are NO(2), CN, Cl, Br, CF(3), F, CHO, CH(2)Cl, COOH, COCH(3), CONH(2), OH, OCH(3...
متن کاملrac-(2R*,3S*,5S*,6R*,7S*,8S*)-7,8-Dichlorobicyclo[2.2.2]octane-2,3,5,6-tetrayl tetraacetate
The title compound, C(16)H(20)Cl(2)O(8), contains a central bicyclo-[2.2.2]octane skeleton with slightly twisted conformation. In this structure, the C-C bond lengths are in the range 1.525 (2)-1.552 (2) Å. Two sides of this skeleton have cis,cis acet-oxy substituents and the Cl atoms have a trans arrangement. An extensive network of weak C-H⋯O interactions stabilizes the crystal structure.
متن کاملCrystal structure of 1,4-diazoniabicyclo[2.2.2]octane diiodide monohydrate
1,4-diazoniabicyclo[2.2.2]octane diiodide monohydrate was synthesized by protonation of 1,4-diazabicyclo[2.2.2]octane (DABCO) with an excess of concentrated hydroiodic acid in water. It forms colourless rodlike crystals. At room temperature an orthorhombic unit cell, space group Cmc21, a 1⁄4 7.781(2) Å, b 1⁄4 13.010(3) Å, c 1⁄4 11.610(2) Å, V 1⁄4 1175.3(4) Å3, Z 1⁄4 4, is observed. Both nitroge...
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