16197-40-3

Usage

Uses

Used in Organic Synthesis:
[S,(+)]-5-Methyl-1-heptene is used as a starting material for the synthesis of various organic compounds. Its unique structure and chiral center make it a valuable component in the creation of complex molecules.
Used in Pharmaceutical Production:
[S,(+)]-5-Methyl-1-heptene is used as an intermediate in the production of various chemicals, including pharmaceuticals. Its specific enantiomeric form can be crucial for the development of effective drugs with minimal side effects.
Used in Fragrance Industry:
[S,(+)]-5-Methyl-1-heptene is also used as an intermediate in the production of fragrances. Its unique chemical properties can contribute to the creation of distinct and appealing scents for various applications.

Upstream product

• 106-95-6 allyl bromide 
• 137-32-6 (-)-2-Methylbutan-1-ol 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 32115-62-1 (S)-(2-methylbutyl)magnesium chloride 
• 534-00-9 (S)-2-methylbutyl bromide 
• 534-00-9 (+)-1-bromo-2-methylbutane 

Downstream Products

• 66007-17-8 (S)-14-Methyl-(Z)-8-hexadecenal 
• 120721-91-7 (S)-5-Methylheptyl-p-toluenesulfonate 
• 57803-73-3 (S)-(+)-5-methyl-1-heptanol 

Relevant academic research and scientific papers

First total synthesis and assignment of the absolute configuration of the neuronal cell protecting alkaloid carbazomadurin B

Using a palladium-catalyzed approach, the first enantio-selective synthesis of the neuronal cell protecting agent carbazomadurin B is described and its absolute configuration is assigned. Georg Thieme Verlag Stuttgart.

Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica

Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.

Silylformylation of chiral 1-alkynes, catalysed by solvated rhodium atoms

Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylation reaction of variously substituted alkynes R1R2CH(CH2)nC≡CH, with catalytic activities comparable with and even higher than more common species such as Rh4(CO)12. Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond. The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the α-position of the unsaturated moiety, to afford enantiomerically enriched β-silylalkenals.