An asatone-type neolignan and its photocage product

Ryouko Yoshihara; Kazuki Mori; Shigeru Nishiyama; Syousuke Yamamura; Hiroyuki Hosomi; Shigeru Ohba; Yoshikatsu Ito

doi:10.1107/S0108270199004205

An asatone-type neolignan and its photocage product

Ryouko Yoshihara, Kazuki Mori, Shigeru Nishiyama, Syousuke Yamamura, Hiroyuki Hosomi, Shigeru Ohba, Yoshikatsu Ito

Department of Humanities and Social Sciences

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The structures of dimethyl 8,8-dimethoxy-7-oxo-1,4-(1, 1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate, C₂₄H₂₈O₁₀, (I), and its photocage product, dimethyl 6,6,12,12-tetramethoxy-5,11-dioxotetracyclo[6.2.2.0^3,10.0 ^4,9]dodecane-2,9-diyldiacrylate, C₂₄H₂₈O₁₀, (II), were determined in order to investigate the conformational change caused by the intramolecular [2+2] photoreaction. The high efficiency (70%) of the photoreaction of (I) in a 1,4-dioxane solution is attributed to the fact that two C=C double bonds in (I) can become close and parallel to each other simply by changing the configuration of the cyclohexene ring moiety from an envelope to a sofa form. Compound (I) is much less photoreactive in the solid state than in solution.

Original language	English
Pages (from-to)	1144-1147
Number of pages	4
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	55
Issue number	7
DOIs	https://doi.org/10.1107/S0108270199004205
Publication status	Published - 1999 Jul 15

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)

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title = "An asatone-type neolignan and its photocage product",

abstract = "The structures of dimethyl 8,8-dimethoxy-7-oxo-1,4-(1, 1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate, C24H28O10, (I), and its photocage product, dimethyl 6,6,12,12-tetramethoxy-5,11-dioxotetracyclo[6.2.2.03,10.0 4,9]dodecane-2,9-diyldiacrylate, C24H28O10, (II), were determined in order to investigate the conformational change caused by the intramolecular [2+2] photoreaction. The high efficiency (70%) of the photoreaction of (I) in a 1,4-dioxane solution is attributed to the fact that two C=C double bonds in (I) can become close and parallel to each other simply by changing the configuration of the cyclohexene ring moiety from an envelope to a sofa form. Compound (I) is much less photoreactive in the solid state than in solution.",

author = "Ryouko Yoshihara and Kazuki Mori and Shigeru Nishiyama and Syousuke Yamamura and Hiroyuki Hosomi and Shigeru Ohba and Yoshikatsu Ito",

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language = "English",

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AU - Yoshihara, Ryouko

AU - Mori, Kazuki

AU - Nishiyama, Shigeru

AU - Yamamura, Syousuke

AU - Hosomi, Hiroyuki

AU - Ohba, Shigeru

AU - Ito, Yoshikatsu

PY - 1999/7/15

Y1 - 1999/7/15

N2 - The structures of dimethyl 8,8-dimethoxy-7-oxo-1,4-(1, 1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate, C24H28O10, (I), and its photocage product, dimethyl 6,6,12,12-tetramethoxy-5,11-dioxotetracyclo[6.2.2.03,10.0 4,9]dodecane-2,9-diyldiacrylate, C24H28O10, (II), were determined in order to investigate the conformational change caused by the intramolecular [2+2] photoreaction. The high efficiency (70%) of the photoreaction of (I) in a 1,4-dioxane solution is attributed to the fact that two C=C double bonds in (I) can become close and parallel to each other simply by changing the configuration of the cyclohexene ring moiety from an envelope to a sofa form. Compound (I) is much less photoreactive in the solid state than in solution.

AB - The structures of dimethyl 8,8-dimethoxy-7-oxo-1,4-(1, 1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate, C24H28O10, (I), and its photocage product, dimethyl 6,6,12,12-tetramethoxy-5,11-dioxotetracyclo[6.2.2.03,10.0 4,9]dodecane-2,9-diyldiacrylate, C24H28O10, (II), were determined in order to investigate the conformational change caused by the intramolecular [2+2] photoreaction. The high efficiency (70%) of the photoreaction of (I) in a 1,4-dioxane solution is attributed to the fact that two C=C double bonds in (I) can become close and parallel to each other simply by changing the configuration of the cyclohexene ring moiety from an envelope to a sofa form. Compound (I) is much less photoreactive in the solid state than in solution.

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An asatone-type neolignan and its photocage product

Abstract

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