178740-32-4

Usage

Uses

Used in Pharmaceutical Research:
Rel-(8R,8'R)-diMethyl-(7S,7'R)-bis(3,4-Methylenedioxyphenyl)tetrahydro-furan is used as a research compound for exploring its potential psychoactive properties and understanding its effects on the human body. The presence of the 3,4-methylenedioxyphenyl group hints at possible interactions with the central nervous system, making it a candidate for further investigation in the development of new therapeutic agents.
Used in Chemical Synthesis:
In the field of organic chemistry, rel-(8R,8'R)-diMethyl-(7S,7'R)-bis(3,4-Methylenedioxyphenyl)tetrahydro-furan may serve as a key intermediate or building block in the synthesis of more complex molecules. Its unique structure and functional groups could be utilized in the creation of novel compounds with specific applications in various industries.
Used in Material Science:
The properties of rel-(8R,8'R)-diMethyl-(7S,7'R)-bis(3,4-Methylenedioxyphenyl)tetrahydro-furan could be harnessed in the development of new materials with tailored characteristics. Its potential use in material science applications may include the creation of advanced polymers, coatings, or other materials with specific properties, such as improved stability or reactivity.
Note: The uses listed above are speculative and based on the information provided. Further research and experimentation are necessary to validate these potential applications and to explore additional uses in various industries.

Upstream product

• 52190-28-0 1-(3,4-(methylenedioxy)phenyl)-2-bromopropan-1-one 
• 110420-30-9 1,4-bis(benzo[d][1,3]dioxol-5-yl)-2,3-dimethylbutane-1,4-dione 
• 28281-49-4 3,4-methylenedioxypropiophenone 
• 75-36-5 acetyl chloride 
• 120-57-0 piperonal 
• 274-09-9 Methylenedioxybenzene 
• 4676-34-0 5,5'-(3,4-dimethylfuran-2,5-diyl)bis(benzo[d][1,3]dioxole) 

Relevant academic research and scientific papers

Lignans from the roots of Saururus chinensis

Four new lignans, saucerneol F (1), saucerneol G (2), saucerneol H (3), and saucerneol I (4), were isolated from the EtOAc extract of the roots of Saururus chinensis, together with one known compound, saucerneol D (5). The structures of compounds 1-4 were

A diastereoselective route to 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans: Protection free synthesis of (+)-galbelgin and (+)-galbacin

An efficient and protection free asymmetric synthesis has been reported for all-trans variant 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans in seven steps from N-succinyl-2-oxazolidinone. (+)-Galbelgin and (+)-galbacin were synthesized in very good overall yields by this route where diastereoselective aldol reaction, stereoselective C-alkylation over O-alkylation and Friedel-Crafts reaction serve as key steps.

Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo

(–)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan, shows potent neurotrophic activities such as neurite-outgrowth promotion and neuroprotection. Previously, we found that (–)-(1S,2R,3S,4R)-stereoisomer 2 exhibited more significant activity than did the natural product talaumidin (1). However, the preparation of optically active (–)-2 requires a complicated synthetic route. To explore new neurotrophic compounds that can be obtained on a large scale, we established a short step synthetic route for talaumidin derivatives and synthesized fourteen analogues based on the structure of (–)-2. First, we synthesized a racemic compound of (–)-2 (2a) and assessed its neurotrophic activity. We found that the neurotrophic property of racemic 2a is similar in activity to that of (–)-2. Using the same synthetic methodology, several talaumidin derivatives were synthesized to optimize the oxy-functionality on aromatic rings. As a result, bis(methylenedioxybenzene) derivative 2b possessed the highest neurotrophic activity. Furthermore, examination of the structure-activity relationships of 2b revealed that the 2,5-diphenyl-tetrahydrofuran structure was an essential structure and that two methyl groups on THF ring could enhance neurotrophic activity. In addition, compounds 2a and 2b were found to induce mouse optic nerve regeneration in vivo.

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.

Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin

An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.