69672-66-8

Basic information

• Product Name: 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]-
• Synonyms: 2,5-Cyclohexadiene-1.4-dione, 2-hydroxy-5-methoxy-3-((1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-
• CAS NO: 69672-66-8
• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.4712
• Mol File: 69672-66-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 477.9°Cat760mmHg
• Flash Point: 159.7°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 3.86E-11mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 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]- (CAS DataBase Reference)
• NIST Chemistry Reference: 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]- (69672-66-8)
• EPA Substance Registry System: 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]- (69672-66-8)

Safety Data

• Hazardous Substances Data: 69672-66-8(Hazardous Substances Data)

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

• 114019-14-6 hyatoquinone 
• 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 
• 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 
• 71678-03-0 ilimaquinone 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 2441-46-5 1,2,4,5-tetramethoxybenzene 
• 583-63-1 ortoquinone 
• 3117-03-1 2,5-dimethoxyquinone 
• 13239-13-9 2,5-dimethoxyhydroquinone 
• 21086-65-7 4,5-dimethoxy-1,2-benzoquinone 
• 1664-27-3 1,2-dihydroxy-4,5-dimethoxybenzene 
• 41722-49-0 (S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 
• 86489-89-6 3-(bromomethyl)-1,2,4,5-tetramethoxybenzene 
• 213026-20-1 (1R,2S,4aS)-trans-decahydro-1α[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2β,4aβ-trimethyl-naphthalen-5-one 

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 articles and documents

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).

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