69672-66-8

Usage

Molecular structure

2,5-Cyclohexadiene-1,4-dione,2-hydroxy-5-methoxy-3-[[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,-8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl]is a complex molecule that contains a cyclohexadiene ring with a dihydroxy-substituted 1,4-dione functionality and a 2-hydroxy-5-methoxy-3-[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,-8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl group.

Functional groups

The compound contains several functional groups, including a cyclohexadiene ring, a 1,4-dione group, a 2-hydroxy group, a 5-methoxy group, and a 3-[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,-8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl group.

Stereochemistry

The compound has a specific stereochemistry, with the R configuration at the 1-position, S configuration at the 2-position, a-S configuration at the 4a-position, and a-S configuration at the 8a-position.

Potential applications

Due to its unique structure and functional groups, the compound has potential applications in the field of organic synthesis and pharmaceutical research.

Complexity

The compound is a complex molecule with a large number of atoms and functional groups, making it a challenging target for synthesis and characterization.

InChI:InChI=1/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h7,11,14,18,24H,6,8-10,12H2,1-5H3

Upstream product

• 71678-03-0 ilimaquinone 
• 121994-56-7 [1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione 
• 259194-86-0 4,5-Dimethoxy-3-((1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone 
• 2441-46-5 1,2,4,5-tetramethoxybenzene 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 259194-79-1 (1R,2S,4aS)-trans-(1,2,3,4,4a,7,8,8a-octahydro)-1α-[(2,3,5,6-tetramethoxyphenyl)-methyl]-1β,2β,4aβ,5-tetramethyl-naphthalene 
• 69672-73-7 [1R-(1β,2β,4aβ,8aα)-3-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione 
• 13239-13-9 2,5-dimethoxyhydroquinone 
• 3117-03-1 2,5-dimethoxyquinone 
• 583-63-1 ortoquinone 
• 86489-89-6 3-(bromomethyl)-1,2,4,5-tetramethoxybenzene 
• 1664-27-3 1,2-dihydroxy-4,5-dimethoxybenzene 
• 259194-83-7 (4aS,5S,8aS)-5,8a-Dimethyl-6-methylene-5-(2,3,5,6-tetramethoxy-benzyl)-octahydro-naphthalen-1-one 
• 213026-15-4 (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene 

Downstream Products

• 157207-60-8 N-[1-R-(1β,2β,4aβ,8aα)-5-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)methyl]-4-hydroxy-3,6-dioxo-1,4-cyclohexadienyl-glycine 
• 1207372-27-7 nakijiquinone K 

Relevant academic research and scientific papers

Unified Synthesis of the Marine Sesquiterpene Quinones (+)-Smenoqualone, (–)-Ilimaquinone, (+)-Smenospongine, and (+)-Isospongiaquinone

The marine sesquiterpene quinones (+)-smenoqualone, (–)-ilimaquinone, (+)-smenospongine, and (+)-isospongiaquinone were efficiently synthesized in a unified manner starting from a known trans-decalin derivative, which is accessible from (+)-5-methyl Wiela

Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Dactylospongia metachromia and Dactylospongia elegans collected from French Polynesia were studied with a particular focus on the variation of the diastereomeric ratio between ilimaquinone (4) and 5-epi-ilimaquinone (5). More than 100 samples, covering an area of 4100km2, were studied to try to clarify this intriguing issue. Nuclear magnetic resonance appeared as the non-destructive, straightforward technique of choice for a relative quantitative study. A random distribution, unique at that point in nature, is observed and leads to biosynthetic considerations. Biological evaluation of both compounds was also performed and showed moderate discrepancies in cytotoxicity and apoptosis induction.

Determination of the absolute stereochemistry of cyclosmenospongine

The absolute stereochemistry of the sponge metabolite cyclosmenospongine (1) was determined as 5R, 8S, 9R, 10S by chemical correlation. Substitution of the methoxyl group by an amino group in the cyclic product 3 of acid-catalyzed rearrangement of ilimaquinone (5) afforded cyclosmenospongine 1. Cyclosmenospongine was also obtained by acid-catalyzed cyclization of smenospongine (6).

Total synthesis and biological evaluation of the nakijiquinones

The Her-2/Neu receptor tyrosine kinase is vastly overexpressed in about 30% of primary breast, ovary, and gastric carcinomas. The nakijiquinones are the only naturally occurring inhibitors of this important oncogene, and structural analogues of the nakijiquinones may display inhibitory properties toward other receptor tyrosine kinases involved in cell signaling and proliferation. Here, we describe the first enantioselective synthesis of the nakijiquinones. Key elements of the synthesis are (i) the reductive alkylation of a Wieland - Mieschertype enone with a tetramethoxyaryl bromide, (ii) the oxidative conversion of the aryl ring into a p-quinoid system, (iii) the regioselective saponification of one of the two vinylogous esters incorporated therein, and (iv) the selective introduction of different amino acids via nucleophilic conversion of the remaining vinylogous ester into the corresponding vinylogous amide. The correct stereochemistry and substitution patterns are completed by conversion of two keto groups into a methyl group and an endocyclic olefin via olefination/reduction and olefination/isomerization sequences, respectively. This synthesis route also gave access to analogues of nakijiquinone C with inverted configuration at C-2 or with an exocyclic instead of an endocyclic double bond. Investigation of the kinase-inhibiting properties of the synthesized derivatives revealed that the C-2 epimer 30 of nakijiquinone C is a potent and selective inhibitor of the KDR receptor, a receptor tyrosine kinase involved in tumor angiogenesis. Molecular modeling studies based on the crystal structure of KDR and a model of the ATP binding site built from a crystal structure of FGF-R revealed an insight into the structural basis for the difference in activity between the natural product nakijiquinone C and the C-2 epimer 30.

Asymmetric synthesis of the nakijiquinones - Selective inhibitors of the Her-2/Neu protooncogene

A Wieland-Miescher type ketone and a tetramethoxyaryl derivative are the key building blocks for the enantioselective total synthesis of nakijiquinone C (1). The nakijiquinones are the only natural products known that selectively inhibit the Her-2/Neu tyr

New quinone from a marine sponge of the order dictyoceratida

Two pigments of quinoid nature, one of which has been identified as ilimaquinone, have been isolated from a hexane extract of a marine sponge Hyatella sp., family Spongiidae, order Dictyoceratida. The second was a new benzoquinone of the drimane series with the composition C22H32O5, which has been called hyatoquinone. Its structure has been established on the basis of spectral characteristics and chemical transformations.