15186-51-3

Usage

Uses

Used in Fragrance Industry:
(methylbutenyl)-methylfuran,2-(3-methyl-2-butenyl)-3-methylfuran is used as a fragrance ingredient for its strong, caramellic aroma. Its natural occurrence and appealing scent make it a valuable addition to the fragrance industry, where it can be used to create a wide range of scents for various products, including perfumes, cosmetics, and cleaning products.
Used in Flavor Industry:
In addition to its use in the fragrance industry, (methylbutenyl)-methylfuran,2-(3-methyl-2-butenyl)-3-methylfuran can also be used as a flavor ingredient. Its caramel aroma can be utilized to enhance the taste of various food and beverage products, providing a rich and complex flavor profile.
Used in Aromatherapy:
Given its natural occurrence and pleasant aroma, (methylbutenyl)-methylfuran,2-(3-methyl-2-butenyl)-3-methylfuran can be used in aromatherapy for its potential therapeutic benefits. Its calming and comforting scent may help to reduce stress and anxiety, promote relaxation, and improve overall well-being.
Used in Research and Development:
As a naturally occurring compound with unique chemical properties, (methylbutenyl)-methylfuran,2-(3-methyl-2-butenyl)-3-methylfuran can be used in research and development for various applications. Scientists and researchers can study its chemical structure and properties to develop new compounds, materials, or processes that can be applied in different industries, such as pharmaceuticals, materials science, or environmental science.

InChI:InChI=1/C10H14O/c1-8(2)4-5-10-9(3)6-7-11-10/h4,6-7H,5H2,1-3H3

Upstream product

• 930-27-8 3-methylfuran 
• 870-63-3 prenyl bromide 
• 2190-48-9 3-chloro-3-methyl-1-butene 
• 77949-41-8 trifluoroacetate de methyl-3 butene-2 ol-2 
• 62823-74-9 3,7-Dimethyl-1,3,6-octatrienyl acetate 
• 130817-56-0 5-Hydroxycitral 
• 130817-55-9 5-Oxogeraniol 
• 84735-63-7 3-methyl-2-(3-methyl-2-butenyl)furan 
• 92356-07-5 2-(3'-hydroxy-3'-methylbutyl)-3-methylfuran 
• 92215-02-6 (2,6-Dimethyl-hepta-1,5-diene-3-sulfinyl)-benzene 
• 149694-46-2 (2Z)-3,7-dimethylocta-2,6-dien-4-yn-1-ol 
• 149694-50-8 3-Hydroxy-2,2-dimethyl-4-(3-methyl-furan-2-yl)-butyric acid 
• 63184-61-2 3-(bromomethyl)furan 
• 81719-68-8 (3-furylmethyl)magnesium bromide 

Downstream Products

• 92356-06-4 rosefuran epoxide 
• 102230-49-9 (6E,10E)-2,6,10-Trimethyl-12-(3-methyl-2-furyl)-8-(4-methylphenylsulfonyl)-2,6,10-dodecatrien 

Relevant academic research and scientific papers

Regioselective Pd(0)-catalyzed coupling reactions on methyl 2,3-dibromofuran-5-carboxylate as a facile entry into 2,3,5-tri- and 2,3-disubstituted furans

Regioselective Pd(0)-catalyzed cross-coupling reactions on the title compound 1 occur at the C-2 carbon atom in excellent yields with a variety of organometallic reagents. The products 2 react under Pd(0)-catalysis at the 3-position with MeZnCl or SnMesu

A Nitrile Oxide Cycloaddition Approach to (-)-Pyrenophorin, and Rosefuran.

Nitrile oxide cycloaddition chemistry has been conveniently applied as carbon-carbon bond forming reaction for the assemblage of the functionalized carbon atom fragments required for the synthesis of two simple but different targets such as the macrolide antibiotic (-)-pyrenophorin 1 and rosefuran 2, a trace component of the high prized oil of rose.In both cases, an intermediate 3,5-disubstituted isoxazoline ring system has been used as serviceable precursor of the the salient structural feature of the targets, namely a γ-oxoacrylate moiety, common to many biologically active compounds, and a β,γ-dihydroxyketone functionality, easily converted by mild acid treatment to rosefuran.

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Synthesis and Catalytic Use of Gold(I) Complexes Containing a Hemilabile Phosphanylferrocene Nitrile Donor

Removal of the chloride ligand from [AuCl(1-κP)] (2) containing a P-monodentate 1′-(diphenylphosphanyl)-1-cyanoferrocene ligand (1), by using silver(I) salts affords cationic complexes of the type [Au(1)]X, which exist either as cyclic dimers [Au(1)]2X2 (3a, X=SbF6; 3 c, X=NTf2) or linear coordination polymers [Au(1)]nXn (3 a′, X=SbF6; 3 b′, X=ClO4), depending on anion X and the isolation procedure. As demonstrated for 3 a′, the polymers can be readily cleaved by the addition of donors, such as Cl-, tetrahydrothiophene (tht) or 1, giving rise to the parent compound 2, [Au(tht)(1-κP)][SbF6] (5 a) or [Au(1-κP)2][SbF6] (4 a), respectively, of which the last two compounds can also be prepared by stepwise replacement of tht in [Au(1-κP)2][SbF6]. The particular combination of a firmly coordinated (phosphane) and a dissociable (nitrile) donor moieties renders complexes 3/3′ attractive for catalysis because they can serve as shelf-stable precursors of coordinatively unsaturated AuI fragments, analogous to those that result from the widely used [Au(PR3)(RCN)]X catalysts. The catalytic properties of the Au-1 complexes were evaluated in model annulation reactions, such as the synthesis of 2,3-dimethylfuran from (Z)-3-methylpent-2-en-4-yn-1-ol and oxidative cyclisation of alkynes with nitriles to produce 2,5-disubstituted 1,3-oxazoles. Of the compounds tested (2, 3 a′, 3 b′, 3 a, 4 a and 5 a), the best results were consistently achieved with dimer 3 c, which has good solubility in organic solvents and only one firmly bound donor at the gold atom. This compound was advantageously used in the key steps of annuloline and rosefuran syntheses.

Iridium(I)-catalyzed coupling of (Z)-2-En-4-yn-1-ols with activated alkynes: A new synthetic route to 7-oxanorbornadienes

Taking advantage of the ability shown by the iridium(I) dimer [{Ir(μ-Cl)(COD)}2] to promote the cycloisomerization of (Z)-enynols into furans, an unprecedented synthetic route to 7-oxanorbornadienes has been developed just by performing the cat

The preparation of 2,3,5-tri- and 2,3-disubstituted furans by regioselective palladium(0)-catalyzed coupling reactions: Application to the syntheses of rosefuran and the F5 furan fatty acid

The 5-acceptor-substituted 2,3-dibromofurans 1 and 2 underwent a regioselective Pd0-catalyzed coupling reaction at the C-2 carbon atom. With alkynes the corresponding 2-alkynylfurans 4 and 5 were accessible (49-97% yield) Alkyl-, aryl-, and alk

A general and facile synthesis of substituted furans by palladium- catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols

A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 °C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

Regiospecific synthesis of polysubstituted furans from silylated furans: Expedient syntheses of rosefuran

By utilizing a sequence of regiospecific lithiation-alkylation, ipso-iodination, boroxine formation, Sonogashira cross-coupling, nickel-catalyzed cross-coupling and Suzuki cross-coupling reactions, several methods have been developed for the syntheses of 2,3-disubstituted furans; 2,4-disubstituted furans, 2,3,4-trisubstituted furans and 2,3,5-trisubstituted furans; Our approach uses as the key theme trimethylsilyl groups as both blacking groups as well as ipso-directing groups. The advantage of this program is aptly illustrated by two expedient syntheses of rosefuran (9c).

A new and efficient synthesis of rosefuran. A general synthesis of furans by palladium-catalysed cycloisomerization of (Z)-2-en-4-yn-1-ols

(Z)-3,7-Dimethylocta-2,6-dien-4-yn-1-ol, readily available from (Z)-3-methylpent-2-en-4-yn-1-ol, undergoes cycloisomerization in the presence of catalytic amounts of K2PdI4 to give rosefuran in high yield.

Structure-Odor Correlation, XXI. Olfactory Properties and Convenient Synthesis of Furans and Thiophenes Related to Rose Furan and Perillene and Their Isomers

Starting from 3-bromofuran (1) or 3-bromothiophene (2) via alkylation in 2-position (-> 3-8) followed by the corresponding second alkylation in 3-position, we obtained rose furan (9), rose thiophene (10), and their analogs 11-16.From the α,β-unsaturated esters 17-20 by hydrogenation (-> 21-24), DIBAH reduction (-> 25-28), and Wittig reaction, perillene (29), thioperillene (30), and their analogs 29-36 were obtained.Olfactory evaluation showed that the difference between the furans and thiophene derivatives is remarkably small, particularly for perillene (29) compared with thioperillene (30), and their analogs.Also the influence of position and structure of the side chain is lower than expected within the compared compounds 9-36. - Keywords: Rose furan / Perillene / Furans / Thiophenes / Structure-odor correlation / Odoriferous substances