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

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)

Access to Document

10.1107/S0108270199004205

Fingerprint Dive into the research topics of 'An asatone-type neolignan and its photocage product'. Together they form a unique fingerprint.

Cite this

Yoshihara, R., Mori, K., Nishiyama, S., Yamamura, S., Hosomi, H., Ohba, S., & Ito, Y. (1999). An asatone-type neolignan and its photocage product. Acta Crystallographica Section C: Crystal Structure Communications, 55(7), 1144-1147. https://doi.org/10.1107/S0108270199004205

@article{c93e9203ea4045a4a0bbd15c4f14e482,

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",

year = "1999",

month = jul,

day = "15",

doi = "10.1107/S0108270199004205",

language = "English",

volume = "55",

pages = "1144--1147",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "International Union of Crystallography",

number = "7",

}

TY - JOUR

T1 - An asatone-type neolignan and its photocage product

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.

UR - http://www.scopus.com/inward/record.url?scp=0141769479&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141769479&partnerID=8YFLogxK

U2 - 10.1107/S0108270199004205

DO - 10.1107/S0108270199004205

M3 - Article

AN - SCOPUS:0141769479

VL - 55

SP - 1144

EP - 1147

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

SN - 0108-2701

IS - 7

ER -