The crystal structure of the title compound, C(20)H(18)N(2)O(8), has been investigated to establish the relative stereochemistry between the ester groups. The cyclo-hexane ring adopts a chair conformation, in which the two ester groups occupy the adjacent equatorial positions in a trans relationship with each other. The mol-ecules assemble in the crystal as chains along the c axis via C-H⋯π inter-actions between the cyclo-hexane ring and a pair of nitro-phenyl rings of the neighbouring mol-ecule. Also observed are π-π stacking inter-actions between the nitro-phenyl rings of neighbouring chains, with a perpendicular distance between these rings of 3.409 Å and a slippage of 0.969 Å.
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http://dx.doi.org/10.1107/S1600536808033874 | DOI Listing |
Synthesis of complex, multiring, spirocyclic, 1,3-dicarbonyl fused, and highly functionalized 5-phenyl-1-azabicyclo[3.1.0]hexanes (ABCH) has been achieved by an intermolecular reaction of 2-(2'-ketoalkyl)-1,3-indandiones or α,γ-diketo esters with (1-azidovinyl)benzenes under transition metal-free conditions.
View Article and Find Full Text PDFOrg Lett
January 2025
Advanced Research Institute and Department of Pharmaceutical Sciences, Taizhou University, Taizhou, Zhejiang 318000, People's Republic of China.
Herein, we present a metal-free, concise, and efficient protocol for the intermolecular reaction of amides (lactams) with donor-acceptor α-diazo esters to afford the functionalized α-amino-α-aroylethanoates. -Methyl-2-pyrrolidone (NMP) and ,-dimethylformamide (DMF) are employed as both reagents and solvents, allowing for the incorporation of all units into the products. The reaction is processed by the ester group migration and compatible with a broad range of substrates up to 50 examples.
View Article and Find Full Text PDFJ Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17, Third Section, South Renmin Road, Chengdu 610041, P. R. China.
A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.
View Article and Find Full Text PDFChem Asian J
January 2025
Indian Institute of Science Education and Research Thiruvananthapuram, chemistry, 2204, School of Chemistry, Vithura, 695551, Thiruvananthapuram, INDIA.
A one-pot methodology for the tandem acylation and oxidative aromatization of vinylogous thioesters to 2-acyl-5-(alkyl/arylthio)phenols is presented. Initially, cyclohexane-1,3-diones were converted to vinylogous thioesters through FeCl3-mediated thioenolization. This was followed by LiTMP-mediated acylation and DDQ-mediated aromatization, which resulted in the synthesis of sulphur derived oxybenzone analogs.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Key Laboratory of Evolution & Marine Biodiversity (Ministry of Education) and Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China.
Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes a cerium-catalyzed cycloaddition of 1-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents.
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