Colouring matters of australian plants. xxii† ventilagone: Crystal structure and an approach to synthesis

Raymond G. Cooke; Anita Liu; Colin L. Raston; Allan H. White

doi:10.1071/CH9800303

Colouring matters of australian plants. xxii† ventilagone: Crystal structure and an approach to synthesis

Raymond G. Cooke, Anita Liu, Colin L. Raston, Allan H. White

Research output: Contribution to journal › Article

8 Citations (Scopus)

Abstract

The crystal structure of the title compound, a naturally occurring tricyclic quinone, C₁₆H₁₆O₅, has been found to be (1R*, 3S*)-7, 10-dihydroxy-1, 3, 8-trimethy1-3, 4, 6, 9-tetrahydro-1H-naphtho[2, 3-c]- pyran-6, 9-dione by single-crystal X-ray diffraction methods at 295(1) K and refined by least squares to a residual of 0·033 for 1143 ‘observed’ reflections. Crystals are monoclinic, P2₁, a 8·346(8), b 16·79(2), c 4·911(5) Å, β 101·17(8)°, Z 2. The molecule is shown to have the cis configuration. As an approach to the synthesis of the pigment the model compound 5-chloro-8-methoxy-1, 3- dimethylisochroman has been prepared and the two racemic forms have been separated and characterized.

Original language	English
Pages (from-to)	303-311
Number of pages	9
Journal	Australian Journal of Chemistry
Volume	33
Issue number	2
DOIs	https://doi.org/10.1071/CH9800303
Publication status	Published - 1980
Externally published	Yes

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Cooke, R. G., Liu, A., Raston, C. L., & White, A. H. (1980). Colouring matters of australian plants. xxii† ventilagone: Crystal structure and an approach to synthesis. Australian Journal of Chemistry, 33(2), 303-311. https://doi.org/10.1071/CH9800303

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title = "Colouring matters of australian plants. xxii† ventilagone: Crystal structure and an approach to synthesis",

abstract = "The crystal structure of the title compound, a naturally occurring tricyclic quinone, C16H16O5, has been found to be (1R*, 3S*)-7, 10-dihydroxy-1, 3, 8-trimethy1-3, 4, 6, 9-tetrahydro-1H-naphtho[2, 3-c]- pyran-6, 9-dione by single-crystal X-ray diffraction methods at 295(1) K and refined by least squares to a residual of 0·033 for 1143 {\textquoteleft}observed{\textquoteright} reflections. Crystals are monoclinic, P21, a 8·346(8), b 16·79(2), c 4·911(5) {\AA}, β 101·17(8)°, Z 2. The molecule is shown to have the cis configuration. As an approach to the synthesis of the pigment the model compound 5-chloro-8-methoxy-1, 3- dimethylisochroman has been prepared and the two racemic forms have been separated and characterized.",

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year = "1980",

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journal = "Australian Journal of Chemistry",

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T2 - Crystal structure and an approach to synthesis

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AU - Liu, Anita

AU - Raston, Colin L.

AU - White, Allan H.

PY - 1980

Y1 - 1980

N2 - The crystal structure of the title compound, a naturally occurring tricyclic quinone, C16H16O5, has been found to be (1R*, 3S*)-7, 10-dihydroxy-1, 3, 8-trimethy1-3, 4, 6, 9-tetrahydro-1H-naphtho[2, 3-c]- pyran-6, 9-dione by single-crystal X-ray diffraction methods at 295(1) K and refined by least squares to a residual of 0·033 for 1143 ‘observed’ reflections. Crystals are monoclinic, P21, a 8·346(8), b 16·79(2), c 4·911(5) Å, β 101·17(8)°, Z 2. The molecule is shown to have the cis configuration. As an approach to the synthesis of the pigment the model compound 5-chloro-8-methoxy-1, 3- dimethylisochroman has been prepared and the two racemic forms have been separated and characterized.

AB - The crystal structure of the title compound, a naturally occurring tricyclic quinone, C16H16O5, has been found to be (1R*, 3S*)-7, 10-dihydroxy-1, 3, 8-trimethy1-3, 4, 6, 9-tetrahydro-1H-naphtho[2, 3-c]- pyran-6, 9-dione by single-crystal X-ray diffraction methods at 295(1) K and refined by least squares to a residual of 0·033 for 1143 ‘observed’ reflections. Crystals are monoclinic, P21, a 8·346(8), b 16·79(2), c 4·911(5) Å, β 101·17(8)°, Z 2. The molecule is shown to have the cis configuration. As an approach to the synthesis of the pigment the model compound 5-chloro-8-methoxy-1, 3- dimethylisochroman has been prepared and the two racemic forms have been separated and characterized.

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