41019-71-0

Basic information

• Product Name: 5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione
• Synonyms: 5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione
• CAS NO: 41019-71-0
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• Mol File: 41019-71-0.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 327 ºC
• Flash Point: 122 ºC
• Appearance: /
• Density: 1.08
• CAS DataBase Reference: 5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione(41019-71-0)
• EPA Substance Registry System: 5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione(41019-71-0)

Safety Data

• Hazardous Substances Data: 41019-71-0(Hazardous Substances Data)

Usage

General Description

5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6-(2H,7H)-naphthalenedione, also known as 2-Hydroxy-2-methyl-3-(2-methylpropyl)-4-oxobutanoic acid, is a chemical compound commonly found in certain species of fungi. It is a member of the naphthalenedione family of organic compounds and is used in medicinal research and drug development due to its potential biological properties. This chemical has been shown to exhibit anti-inflammatory and anti-fungal properties, making it of interest in the development of new pharmaceuticals. Its unique molecular structure and biological activities make it an area of interest for further investigation and potential therapeutic applications.

Upstream product

• 31062-32-5 5,5-ethylenedioxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2[3H]-naphthalenone 
• 124618-30-0 C₁₇H₂₄O₆ 
• 124618-31-1 C₁₆H₂₄O₅ 
• 1629-58-9 4-penten-3-one 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 78-94-4 methyl vinyl ketone 
• 97025-02-0 (+/-)-3,4,8,8a-tetrahydro-8a-methyl-5-methoxycarbonyl-1,6(2H,7H)-naphthalenedione 
• 57440-68-3 2-methyl-2-(3-oxopentyl)-1,3-cyclohexanedione 
• 32830-97-0 1-chloro-3-pentanone 

Downstream Products

• 4586-01-0 (+/-)-α-costal 
• 4586-01-0 (+/-)-epi-α-costal 
• 11024-56-9 paspaline 
• 82225-47-6 (+/-)-ajugarin-IV 
• 134827-28-4 6-((1S,2S,8aR)-2-Cyano-5,8a-dimethyl-6-oxo-4-phenylselanyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-2,4,4-tris-methoxycarbonyl-6-oxo-hex-2-enoic acid methyl ester 
• 134827-35-3 C₂₉H₄₁NO₇S₂ 
• 134827-27-3 2-[2-((1S,2S,8aR)-2-Cyano-5,8a-dimethyl-6-oxo-4-phenylselanyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-ethyl]-malonic acid dimethyl ester 
• 108401-51-0 (1'R,4'aR,8'aR)-6'-[1,3]Dioxolan-2-yl-1',4'a-dimethyl-6'-phenylselanyl-7'-vinyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one 
• 108401-43-0 (1'S,4'aS,8'aS)-1',4'a-Dimethyl-6'-phenylselanyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one 
• 65018-15-7 2-((2S,4aR,8aR)-4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-prop-2-en-1-ol 
• 107449-59-2 (1S,4aS,5S)-1-Benzyl-5-benzyloxy-1,4a-dimethyl-3,4,4a,5,6,7-hexahydro-1H-naphthalen-2-one 
• 107449-61-6 Benzoic acid (4'aS,5'S)-1',4'a-dimethyl-4',4'a,5',6',7',8'-hexahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl ester 
• 107449-62-7 Benzoic acid 1',4'a-dimethyl-3',4',4'a,5',6',7'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl ester 
• 102058-66-2 Benzoic acid (1S,8aS)-5,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 

Relevant articles and documents

Total Synthesis of Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structural Reassignment of Dysiherbol A

The first total synthesis of marine anti-cancer meroterpenoids dysideanone B and dysiherbol A have been accomplished in a divergent way. The synthetic route features: 1) a site and stereoselective α-position alkylation of a Wieland–Miescher ketone derivative with a bulky benzyl bromide to join the terpene and aromatic moieties together and set the stage for subsequent cyclization reactions; 2) an intramolecular radical cyclization to construct the 6/6/6/6-tetracycle of dysideanone B and an intramolecular Heck reaction to forge the 6/6/5/6-fused core structure of dysiherbol A. A late-stage introduction of the ethoxy group in dysideanone B reveals that this group might come from the solvent ethanol. The structure of dysiherbol A has been revised based on our chemical total synthesis.

Stereocontrolled synthesis of the AB rings of samaderine C

A concise synthesis of the AB rings of samaderine C (12 steps, 8 isolation steps, 7.8% overall yield), a quassinoid with antifeedant and insecticidal activity, is described. The development of the first general approach to the trans-1,2-diol A-ring motif

Synthesis of 12-epi-Protopanaxadiol and Formal Synthesis of Ginsenoside Chikusetsusaponin-LT8

In the context of the total synthesis of protopanaxadiol, two strategies were explored. One strategy from an optically active trienic epoxide, possessing a 5-membered ring, prepared from (S)-epoxy-limonene and (S)-epoxyfarnesol, which was submitted to Ti-(III)-mediated radical cascade to afford an original tetracyclic structure resulting from a 6-endo-trig 6-endo-trig 8-endo-trig process. A second strategy, starting from a Wieland-Miescher-type ketone, using a “ring-by-ring” synthesis allowed the synthesis of 12-epi-protopanaxadiol. In this latter strategy, an efficient sequence of reactions to install the two vicinal C8–C14 quaternary centers involves: i) a Barbier type reaction; ii) an oxidative allylic transposition and iii) a nickel-catalyzed addition of trimethylaluminium. By using this second strategy, 20-hydroxydammar-24-ene-3,12-dione was synthesized which represents a formal synthesis of chikusetsusaponin-LT8, isolated from Panax japonicus.