(3aRS,7aSR)-7a-Methoxy-2-oxo-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4,4-dicarbonitrile (original) (raw)
2012, Acta Crystallographica Section E Structure Reports Online
AI-generated Abstract
The racemic compound (3aRS,7aSR)-7a-Methoxy-2-oxo-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4,4-dicarbonitrile is characterized by a unique [4.3.0] bicyclic structure with specific conformational features. The synthesis involves an intramolecular Michael addition reaction, resulting in a bicyclic γ-lactone that serves as an important intermediate for producing various natural products. Crystal data and intermolecular interactions reveal weak C-H···O bonds that contribute to the compound's stability and arrangement in the crystalline state.
Sign up for access to the world's latest research.
checkGet notified about relevant papers
checkSave papers to use in your research
checkJoin the discussion with peers
checkTrack your impact
Related papers
Acta Crystallographica Section E-structure Reports Online, 2014
Acta Crystallographica Section E Structure Reports Online, 2012
In the title compound, C 23 H 38 O 5 , the oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride unit has a normal geometry and the tetradecoxymethyl side chain is fully extended. In the crystal, molecules are linked head-to-head by C-HÁ Á ÁO hydrogen bonds, forming two-dimensional networks propagating along the a and c-axis directions. Related literature Olefinic hydrogenation of an oxabicyclo[2.2.1]hept-5-ene derivative using catalytic quantities of 10% Pd on carbon as catalyst afforded the title compound. For reviews on the Diels-Alder reaction, see: Oppolzer (1991); Pindur et al. (1993). For a review on asymmetric cycloaddion processes, see: Pellissier (2012). For a review on catalytic hydrogenations, see: Brieger & Nestrick (1974). For a review on asymmetric catalytic hydrogenation processes, see: Knowles (2002). For discussions on reaction mechanisms with specifics on kinetic and thermodynamic control, see: Lowry & Richardson (1987); Smith (2012). For a discussion on Diels-Alder selectivity using maleic anhydride, see: Palmer (2004). Experimental Crystal data C 23 H 38 O 5 M r = 394.53 Monoclinic, P2 1 =n a = 6.8541 (5) Å b = 35.206 (4) Å c = 9.2992 (7) Å = 99.060 (7) V = 2216.0 (3) Å 3 Z = 4 Mo K radiation = 0.08 mm À1 T = 180 K 0.47 Â 0.17 Â 0.02 mm Data collection Agilent Xcalibur Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T min = 0.865, T max = 1.000 9120 measured reflections 4053 independent reflections 2974 reflections with I > 2(I) R int = 0.028 Refinement R[F 2 > 2(F 2)] = 0.049 wR(F 2) = 0.108 S = 1.04 4053 reflections 255 parameters H-atom parameters constrained Á max = 0.18 e Å À3 Á min = À0.19 e Å À3 organic compounds o3374 Kelly et al.
Acta Crystallographica Section E Structure Reports Online, 2008
Octa-n-butyl-1j 2 C,2j 2 C,3j 2 ,4j 2 C-bis(l-2,3-dibromopropionato)-1:2j 2 O:O 0 0 0 ,-3:4j 2 O:O 0 0 0-bis(2,3-dibromopropionato)-1jO,3jO-di-l 3-oxido-1
Loading Preview
Sorry, preview is currently unavailable. You can download the paper by clicking the button above.
Related papers
Acta Crystallographica Section E Structure Reports Online, 2010
2,2,7,7-Tetramethyl-1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione
Acta Crystallographica Section E Structure Reports Online, 2012
Acta Crystallographica Section E Structure Reports Online, 2012
Acta Crystallographica Section E Structure Reports Online, 2012