Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Yuya Suzuki, Isao Takahashi, Yasuo Dobashi, Hiroshi Hasegawa, Christian Roussel, Osamu Kitagawa

研究成果: Article査読

9 被引用数 (Scopus)

抄録

The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.

本文言語English
ページ(範囲)132-135
ページ数4
ジャーナルTetrahedron Letters
56
1
DOI
出版ステータスPublished - 2015 1 1

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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