97743-96-9

Basic information

• Product Name: xestoquinone
• Synonyms: xestoquinone;(12bS)-1,2,3,12b-Tetrahydro-12bβ-methyl-6H-benzo[6,7]phenanthro[10,1-bc]furan-6,8,11-trione;(12bS)-12b-Methyl-2,3-dihydro-1H-5-oxabenzo[k]acephenanthrylene-6,8,11(12bH)-trione;[12bS,(+)]-1,2,3,12b-Tetrahydro-12bβ-methyl 5(6H)-oxabenzo[k]acephenanthrylene-6,8,11-trione;(12bS)-2,3-Dihydro-12b-methyl-1H-benzo[6,7]phenanthro[10,1-bc]furan-6,8,11(12bH)-trione
• CAS NO: 97743-96-9
• Molecular Formula: C20H14O4
• Molecular Weight: 318.32276
• Mol File: 97743-96-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 567.8°Cat760mmHg
• Flash Point: 284.3°C
• Appearance: /
• Density: 1.415
• Vapor Pressure: 6.58E-13mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: xestoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: xestoquinone(97743-96-9)
• EPA Substance Registry System: xestoquinone(97743-96-9)

Safety Data

• Hazardous Substances Data: 97743-96-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H14O4/c1-20-6-2-3-10-9-24-19(17(10)20)18(23)13-7-11-12(8-14(13)20)16(22)5-4-15(11)21/h4-5,7-9H,2-3,6H2,1H3/t20-/m0/s1

Upstream product

• 127232-66-0 (4aR,5S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5-<(methoxymethoxy)methyl>-8a-methyl-1(2H)-naphthalenone 
• 127232-63-7 (4aR,5S,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-<(methoxymethoxy)methyl>-8a-methyl-1(2H)-naphthalenone 1-ethylene acetal 
• 127255-10-1 (4aS,8S,8aR)-4a,5,6,7,8,8a-hexahydro-8-<(methoxymethoxy)methyl>-4a-methyl-2(1H)-naphthalenone 
• 117439-20-0 (4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal 
• 127232-62-6 (4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-<(methoxymethoxy)methyl>-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal 
• 183727-69-7 12b-methyl-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one 
• 158991-34-5 4,7-dimethoxybenzofuran 
• 188648-37-5 12b-methyl-2,3-dihydro-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one 
• 127232-71-7 (4S,12bS)-1,2,3,4-tetrahydro-5-hydroxy-8,11-dimethoxy-4-<(methoxymethoxy)methyl>-12b-methyl-6(12bH)-benzanthracenone 
• 127232-70-6 (4S,4aR,12bR)-1,2,3,4,4a,12b-hexahydro-8,11-dimethoxy-4-<(methoxymethoxy)methyl>-12b-methyl-6(5H)-benzanthracenone 
• 127232-67-1 C₂₁H₃₂N₂O₄S 
• 127232-72-8 (4S,12bS)-1,2,3,4-tetrahydro-5-hydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)-benzanthracenone 
• 127232-69-3 (4S,4aR,6aξ,12aξ,12bR)-1,2,3,4,4a,6a,7,12,12a,12b-decahydro-8,11-dimethoxy-4-<(methoxymethoxy)methyl>-12b-methyl-6(5H)-benzanthracenone 
• 127232-64-8 O-<(4aR,5S,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5-<(methoxymethoxy)methyl>-8a-methyl-1(2H)-oxonaphthalen-6-yl>S-methyl dithiocarbonate ethylene acetal 

Relevant articles and documents

Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B

The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6-7 steps using an easily accessiblemeso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B-C ring and the all-carbon quaternary stereocenter at C-6 were preparedviaa desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D-E ring was constructed through a sequence of Ti(Oi-Pr)4-promoted photoenolization/Diels-Alder, dehydration, and aromatization reactions. This asymmetric strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies.

Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

Syntheses of (±)-xestoquinone, (±)-9-methoxyxestoquinone and (±)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolite

Intramolecular Diels-Alder and Cope reactions of o-quinonoid monoketals and their adducts: Efficient syntheses of (±)-xestoquinone and heterocycles related to viridin

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