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Atropisomers of 1-(Acyl or Aroyl)-2-naphthylindolines. Isolation, X-Ray Crystal Structure and Conformational Analysis
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- Ito Fumikazu
- Faculty of Pharmaceutical Sciences, Kumamoto University
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- Moriguchi Tetsuya
- Faculty of Pharmaceutical Sciences, Kumamoto University
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- Yoshitake Yasuyuki
- Faculty of Pharmaceutical Sciences, Kumamoto University
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- Eto Masashi
- Faculty of Pharmaceutical Sciences, Kumamoto University
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- Yahara Shoji
- Faculty of Pharmaceutical Sciences, Kumamoto University
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- Harano Kazunobu
- Faculty of Pharmaceutical Sciences, Kumamoto University
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Description
A series of pairs of stable diastereomeric atropisomers caused by restricted rotation around the Csp3–Csp2 bond of [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-(3- or 4-substituted phenyl)-methanone or [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-1-alkanone were isolated. The conformational analyses of the atropisomers were performed based on the X-ray crystallographic and 1H-NMR spectral data. It became clear that rotation about the C2–naphthyl bond is restricted at room temperature, whereas the >NCO–Ar bond rotates freely.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 51 (6), 688-696, 2003
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679140142080
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- NII Article ID
- 110003615377
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- NII Book ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD3sXls1Knt70%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6541694
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- PubMed
- 12808248
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- Text Lang
- en
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- Article Type
- journal article
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- Data Source
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- JaLC
- NDL Search
- Crossref
- PubMed
- CiNii Articles
- OpenAIRE
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- Abstract License Flag
- Disallowed