41744-26-7

Basic information

• Product Name: Eupomatenoid 6
• Synonyms: Eupomatenoid 6;4-[3-Methyl-5-[(E)-1-propenyl]benzofuran-2-yl]phenol;Ratanhiaphenol II;rataniaphenol II
• CAS NO: 41744-26-7
• Molecular Formula: C₁₈H₁₆O₂
• Molecular Weight: 0
• Mol File: 41744-26-7.mol

Chemical Properties

• Boiling Point: 421.9°C at 760 mmHg
• Flash Point: 208.9°C
• Appearance: /
• Density: 1.162g/cm³
• Vapor Pressure: 1.03E-07mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: Eupomatenoid 6(CAS DataBase Reference)
• NIST Chemistry Reference: Eupomatenoid 6(41744-26-7)
• EPA Substance Registry System: Eupomatenoid 6(41744-26-7)

Safety Data

• Hazardous Substances Data: 41744-26-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Eupomatenoid 6 is used as a bioactive compound for its potential therapeutic applications. The expression is: Eupomatenoid 6 is used as a pharmaceutical agent for its potential medicinal properties derived from the roots of Krameria lappa.
Used in Research and Development:
In the field of research and development, Eupomatenoid 6 is used as a subject of study for understanding its chemical structure, biological activities, and potential applications in drug discovery. The expression is: Eupomatenoid 6 is used as a research subject for exploring its chemical and biological properties and its potential role in drug development.
Used in Traditional Medicine:
Eupomatenoid 6 may also be utilized in traditional medicine, where it could be employed for its potential health benefits and therapeutic effects. The expression is: Eupomatenoid 6 is used as a traditional medicine ingredient for its potential health benefits and therapeutic applications derived from Krameria lappa roots.

InChI:InChI=1/C18H16O2/c1-3-4-13-5-10-17-16(11-13)12(2)18(20-17)14-6-8-15(19)9-7-14/h3-11,19H,1-2H3/b4-3+

Upstream product

• 568593-04-4 2-(4-Methoxy-phenyl)-3-methyl-5-((E)-propenyl)-benzofuran 
• 123-11-5 4-methoxy-benzaldehyde 
• 86253-69-2 4-Acetoxy-benzoic acid 2-(1-bromo-ethyl)-4-(1-bromo-propyl)-phenyl ester 
• 86253-68-1 2-ethyl-4-propylphenyl 4-acetoxybenzoate 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 489422-99-3 {4-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}-tert-butyldimethylsilane 
• 365448-15-3 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)phenoxy]dimethylsilane 
• 67963-68-2 t-butyldimethylsilyl-4-bromophenol 
• 568593-05-5 2,3,5-tribromo-2,3-dihydrobenzofuran 
• 64150-67-0 2,3,5-tribromobenzofuran 
• 99660-97-6 dibromo-3,5 benzofuranne 
• 23145-07-5 5-bromobenzofuran 
• 65440-82-6 O-(4-bromophenyl)hydroxylamine 
• 70-70-2 4-hydroxypropiophenone 

Downstream Products

• 1609690-96-1 E-[4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltri-O-benzoyl]-α-L-rhamnopyranoside 
• 130659-21-1 iso-ratanhiaphenol A 
• 130659-21-1 iso-ratanhiaphenol B 
• 130659-22-2 iso-ratanhiaphenol D 
• 130659-22-2 iso-ratanhiaphenol C 
• 40341-60-4 4-(3-Methyl-5-propyl-benzofuran-2-yl)-phenol 
• 40341-58-0 (E)-2-(4-methoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 

Relevant articles and documents

Synthetic method for eupomatenoid-6

The present invention relates to a simple method for synthesizing a natural benzofuran derivative eupomatenoid 6 by using a horner-emmons type condensation reaction as a main step. In addition, the polarity reversal properties of an aldehyde derivative andalpha;-aminophosphonate are effectively used for the reaction. Deoxybenzoin is obtained by reacting the andalpha;-aminophosphonate from anisaldehyde with 5-bromo-2-methoxybenzaldehyde, using the horner-emmons type condensation, and then the obtained deoxybenzoin is methylated and becomes a benzofuran structure with remarkable yield via random demethylation-cyclodehydration. Finally, the eupomatenoid 6 is obtained at 56.8% of the total yield from a total of five steps by a Suzuki coupling reaction with propenyl boronic acid.COPYRIGHT KIPO 2016

One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols

(Chemical Equation Presented) A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excelle

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6

Matrix presented. A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran

Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15

Regioselective C-C-bond formation reactions at 2,3-dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (6) were studied. Pd-catalyzed Sonogashira and Negishi cross-coupling occurred with perfect regioselectivity at carbon atom C-2 to provide 2-substituted 3-bromobenzofurans (12, 14) and 3,5-dibromobenzofurans (17, 18) in 50-91% yield. A regioselective displacement of the bromine substituents in 3,5-dibromobenzofurans 18 was achieved by a halogen-metal exchange reaction at carbon atom C-3 and by a Nicatalyzed Kumada cross-coupling at C-5. The methodology was applied to the synthesis of eupomatenoids 3, 4, 5, 6, and 15 (5). The synthesis of these compounds was achieved in overall yields of up to 60%.

Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions

Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribromobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high

Natural Benzofuranes. Synthesis of Eupomatenoids-1, -3, -4, -5, -6, -7, and -13

A group of eupomatenoids, natural lignans possessing 2-aryl-3-methyl-5-propenylbenzofuran structures have been synthesized by short pathways which include the intramolecular Wittig reaction of an o-bromoethylaryl benzoate ester as a key step.