167777-52-8

Usage

General Description

"1,3-Dioxolane, 2,2-dimethyl-4-[(1S,2E)-2-methyl-1-(phenylmethoxy)-2-butenyl]-, (4R)-" is a chemical compound with the molecular formula C15H24O3. It is also known as nepetalactone, a natural organic compound found in the essential oil of catnip (Nepeta cataria). Nepetalactone is known for its effects on cats, causing euphoria and excitement when they come into contact with it. Due to these effects, it is often used in cat toys and repellents. Nepetalactone has also been studied for potential pharmaceutical applications, including insect repellent and insecticide properties. However, its potential effects on humans are still being researched.

Upstream product

• 88424-95-7 2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol 
• 100-44-7 benzyl chloride 
• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 
• 109121-41-7 (R)-4-((1S,2R)-1-benzyloxy-2-methylbut-3-enyl)-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 333302-67-3 (E)-(2R,3S)-3-benzyloxy-4-methyl-hex-4-ene-1,2-diol 

Relevant academic research and scientific papers

The Anionic [1,3]-H-Shift Applied in Synthesis: A Novel Access to (+)-Citreoviral

In this paper we present a highly stereoselective and concise synthesis of the tetrahydrofuran derivative 3 and thus, a formal synthesis of the mycotoxin metabolite (+)-citreoviral (2). In our route we made use of a novel anionic [1,3]-H-shift to convert the homoallylic alcohol 9 into the allylic benzyl ether 10. Another key step was the regio- and stereo-controlled cyclization of epoxide 18b to tetrahydrofuran 19b, which was then converted into ester 3.

A mechanistically unusual base induced [1,3]-H-shift in homoallylic ethers

Upon treatment with NaH in DMF the homoallylic ethers 1a-g and the amine 1h undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of 1a and 1b show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mode.

Synthesis of optically active β,γ-unsaturated α-amino acids of α,β-unsaturated γ-amino acids. S(N)2- vs. S(N)2'-dichotomy of the Mitsunobu amination of allylic alcohols

Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean S(N)2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities.