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

7 引用 (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.

元の言語English
ページ(範囲)132-135
ページ数4
ジャーナルTetrahedron Letters
56
発行部数1
DOI
出版物ステータスPublished - 2015 1 1

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Ground state
Crystal structure
Nuclear magnetic resonance
X rays
3,4-dihydroquinolin-2-one

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one. / Suzuki, Yuya; Takahashi, Isao; Dobashi, Yasuo; Hasegawa, Hiroshi; Roussel, Christian; Kitagawa, Osamu.

:: Tetrahedron Letters, 巻 56, 番号 1, 01.01.2015, p. 132-135.

研究成果: Article

Suzuki, Yuya ; Takahashi, Isao ; Dobashi, Yasuo ; Hasegawa, Hiroshi ; Roussel, Christian ; Kitagawa, Osamu. / Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one. :: Tetrahedron Letters. 2015 ; 巻 56, 番号 1. pp. 132-135.
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abstract = "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.",
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T1 - Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

AU - Suzuki, Yuya

AU - Takahashi, Isao

AU - Dobashi, Yasuo

AU - Hasegawa, Hiroshi

AU - Roussel, Christian

AU - Kitagawa, Osamu

PY - 2015/1/1

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N2 - 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.

AB - 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.

KW - Amination

KW - Axially chiral

KW - Distortion

KW - Quinolinone

KW - Rotational barrier

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