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Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle.
Gao, Chao; Li, Hongchen; Zhao, Jing; Bu, Lulu; Sun, Mei; Wang, Jingrui; Tao, Gang; Wang, Longde; Li, Li; Wen, Guilin; Hu, Yunhu.
Affiliation
  • Gao C; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Li H; CNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, China.
  • Zhao J; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Bu L; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Sun M; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Wang J; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Tao G; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Wang L; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Li L; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Wen G; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
  • Hu Y; School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.
Molecules ; 29(14)2024 Jul 17.
Article in En | MEDLINE | ID: mdl-39064941
ABSTRACT
A novel axially chiral all-hydrocarbon cyclo[7] (1,3-(4,6-dimethyl)benzene (CDMB-7) was designed and synthesized using atroposelective[2 + 5] cyclization through Suzuki-Miyaura coupling. CDMB-7 adopts an irregular bowl-like shape with C2 symmetry and exhibits two diastereoisomers in its crystallographic structure. The conformational isomers of CDMB-7 racemates remain stable at high temperatures (393 K). High-performance liquid chromatography (HPLC) confirmed that a single chiral isomer will spontaneously undergo racemization within 30 min at room temperature. This finding opens up possibilities for achieving adaptive chirality in all-hydrocarbon cyclo[7] m-benzene macrocycles.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Molecules Journal subject: BIOLOGIA Year: 2024 Type: Article Affiliation country: China
Fulltext
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Molecules Journal subject: BIOLOGIA Year: 2024 Type: Article Affiliation country: China