55968-41-7

Usage

Uses

Used in the Food Industry:
(Z)-Oct-5-en-2-ol is used as a flavoring agent for its appealing green apple-like aroma, enhancing the sensory experience of various food products.
Used in the Perfume Industry:
(Z)-Oct-5-en-2-ol is utilized in the production of perfumes, where its unique scent contributes to the creation of distinct and attractive fragrances.
Used in the Cosmetic Industry:
(Z)-Oct-5-en-2-ol serves as a fragrance in a range of cosmetic products, adding to their appeal and enhancing consumer experience.
Used in the Chemical Industry:
Due to its antimicrobial properties, (Z)-Oct-5-en-2-ol is employed in the development of antimicrobial agents, which have potential applications in various sectors requiring sanitization and preservation.

InChI:InChI=1/C8H16O/c1-3-4-5-6-7-8(2)9/h4-5,8-9H,3,6-7H2,1-2H3/b5-4-

Synthetic route

(Z)-4-heptenal (6728-31-0) + methylmagnesium bromide (75-16-1) → cis-5-octen-2-ol (55968-41-7)

Conditions	Yield
Stage #1: (Z)-4-heptenal; methylmagnesium bromide In tetrahydrofuran; toluene at -78 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran; toluene	83%

cis-5-octen-2-ol (55968-41-7) + tert-butyl (methylsulfonyl)carbamate (147751-16-4) → (Z)-tert-butyl methylsulfonyl(oct-5-en-2-yl)carbamate (1214888-41-1)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16h;	82%

cis-5-octen-2-ol (55968-41-7) + methanesulfonyl chloride (124-63-0) → cis-5-Octen-2-yl Methanesulfonate

Conditions	Yield
With pyridine at 0 - 5℃;

cis-5-octen-2-ol (55968-41-7) → (Z)-5-octen-2-yl hydroperoxide (89122-02-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 0 - 5 °C 2: H2O2, KOH / methanol; H2O / 1.) 0-5 deg C, 2.) room temperature View Scheme

Upstream product

• 6728-31-0 (Z)-4-heptenal 
• 75-16-1 methylmagnesium bromide 

Relevant academic research and scientific papers

New modes for the osmium-catalyzed oxidative cyclization

(Figure Presented) The osmium-catalyzed oxidative cyclization of amino alcohol initiators formally derived from 1,4-dienes Is an effective method for the construction of pyrrolidines, utilizing a novel reoxidant (4-nltropyridlne N-oxide = NPNO). The cyclization of enantlopure syn- and anti-amino alcohols gives rise to enantlopure cis- and frans-2,5-disubstituted pyrrolidines, respectively. Moreover, the cyclization of Ws-homoallylic amines bearing an exocyclic chelating group Is shown to be a complementary method for irans-pyrrolidine formation.