67242-75-5

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-1-Chloro-2-nonene is used as an intermediate in the synthesis of Falcarinol (F101100), a covalent cannabinoid CB1 receptor antagonist. It is known to induce pro-allergic effects in the skin, making it a potential candidate for the development of new drugs targeting allergic reactions and inflammation.

Upstream product

• 97463-22-4 1-[(Z)-2-nonenyl]piperidine 
• 21369-64-2 n-hexyllithium 
• 41453-56-9 (Z)-2-nonen-1-ol 
• 541-41-3 chloroformic acid ethyl ester 

Relevant academic research and scientific papers

A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group

Figure Presented. A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (±)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.

Copper-catalyzed hydroallylation of allenes employing hydrosilanes and allyl chlorides

The hydroallylation of allenes was developed by employing a hydrosilane and allyl chlorides in the presence of a copper catalyst. The reaction provided (E)-1,5-dienes mainly in good to high yields.

α-Selective Allylation of Isatin Imines Using Metallic Barium

The Barbier-type allylation of isatin imines with allylic chlorides was achieved by using metallic barium as the promoter. Various α-allylated 3-amino-2-oxindoles were synthesized from the corresponding allylic chlorides and isatin imines. The double-bond geometry of allylic chlorides was retained throughout the reaction. An arylic bromide or iodide functionality of the products was robust to metalation under the optimum reaction conditions.

Formation of isoxazolidines by enantioselective copper-catalyzed annulation of 2-nitrosopyridine with allylstannanes

Click! Formal [3+2] cycloadditions of 2-nitrosopyridine with various allylstannanes give 4-stannyl-substituted isoxazolidines. The use of [Cu(MeCN)4]PF6, in combination with a Walphos ligand, leads to excellent enantioselectivies and high yields. With cis-2- alkenylstannanes as nucleophiles, 3-alkyl-4-stannyl-substituted isoxazolidines are formed with excellent diastereo- and enantioselectivities. Copyright

Alkenyl-copper derivatives. 28 (1) : Stereospecific synthesis of tertiary allylic amines of E and Z configuration

Aminoethers and aminothioethers react smoothly with organocopper and cuprate reagents to afford tertiary amines.The use of Z alkenyl cuprates or E alkenyl aluminium derivatives leads to Z or E tertiary allylic amines.Polysubstituted and variously functionalized alkenyl copper reagents react in the same way, and a straightforward synthesis of pure N,N-diethylnerylamine is described.The stereoisomeric purity of these allylic amines is in the 99.5-99.9percent range, and their conversion to the corresponding allylic chlorides is not accompanied by any stereochemical scrambling.