287471-30-1

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Chloro-6,6-dimethyl-2-hepten-4-yne is used as a pharmaceutical intermediate for the synthesis of terbinafine, an allylamine antifungal agent. It plays a crucial role in inhibiting the COX-fungal squalene, leading to a reduction in membrane ergosterol. This reduction in ergosterol synthesis effectively inhibits the growth of fungi, making it a valuable component in the development of antifungal medications.
2. Used in Antifungal Applications:
1-Chloro-6,6-dimethyl-2-hepten-4-yne is employed as an active ingredient in the development of antifungal drugs. Its ability to target and inhibit specific stages of fungal growth, particularly the ergosterol synthesis, makes it a potent agent against various fungal infections. It does not affect the synthesis of other precursors, making it a selective and effective compound in antifungal treatments.

Synthesis

1-Chloro-6,6-dimethyl-2-hepten-4-yne mainly due to keratin aggregation produce squalene, was squalene cyclooxygenase inhibition, squalene in the cells of a large number gathered in the form of lipid droplets penetrate fungal cell membrane, destruction of the membrane lipid composition, resulting in fungal death. A typical procedure for preparing of 1-chloro-6,6-dimethyl-2-hepten-4-yne using boron trichloride is as follows: Compound 1 (53 g, 0.38 mol) in 2800 mL of n-hexane was cooled to 10～15℃. Boron trichloride (1 M in hexane, 480 mL, 0.48 mol) was added to the mixture at 15～20℃ over a 10 min period. After 10 min of stirring at 20℃, the mixture was quenched with 1000 mL of water and stirred for 10 min. The separated organic phase was washed with 20% NaCl, dried (MgSO4), and evaporated to afford the title compound 2 (57.1 g, 95%) in 9:1 E:Z ratio.

InChI:InChI=1/C9H13Cl/c1-9(2,3)7-5-4-6-8-10/h4,6H,8H2,1-3H3/b6-4+

Upstream product

• 78629-20-6 3-hydroxy-6,6-dimethylhept-1-ene-4-yne 
• 108-10-1 4-methyl-2-pentanone 

Downstream Products

• 78628-80-5 terbinafine hydrochloride 
• 91161-71-6 terbinafin 
• 176168-78-8 N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthylmethyl amine hydrochloride 

Relevant academic research and scientific papers

A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: A key intermediate for terbinafine

A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4- yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1(max)). The resulting (E)-1-halo-6,6- dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally related enyne alcohols have been studied likewise and shown similar versatility. (C) 2000 Elsevier Science Ltd.

A PROCESS FOR THE PURIFICATION OF 1-HALO-6,6-DIMETHYL-HEPT-2-ENE-4-YNE

The invention relates to a process for purification of 1-halo-6,6-dimethyl-hept-2-ene-4-yne of Formula (I), wherein X represents a halogen atom subjecting crude 1-halo-6,6-dimethyl-hept-2-ene-4-yne to distillation under reduced pressure to obtain pure 1-halo-6,6-dimethyl-hept-2-ene-4-yne. This compound is an important intermediate for the production of the widely used antifungal drug Terbinafine.

Process for the preparation of terbinafine and salts thereof

A process for the preparation of Terbinafine and salts thereof by reacting 1-chloro-6,6-dimethylhept-2-en-4-yne and N-methyl-N-(1-naphthylmethyl)amine in a basic aqueous medium is disclosed. Also disclosed is a process for the preparation of 1-chloro-6,6-dimethylhept-2-en-4-yne.

PROCESS FOR PREPARING A SUBSTITUTED ALLYLAMINE DERIVATIVE AND THE SALTS THEREOF

The antifungal agent (E)-N-methyl-N-(1-naphthylmethyl)-6,6-dimethyl-hept-2-ene-4-ynyl-1-amine of formula (I)and acid addition salts thereof are prepared by reacting a chloro-compound of formula (IIIb)with a secondary amine of formula (II)in an aliphatic ketone-type solvent in the presence of a base and optionally iodide salt catalyst, and subsequently treating the resulting reaction mixture directly with aqueous hydrochloric acid to precipitate the hydrochloride of the compound of formula (I). The precipitate is separated, and the base of formula (I) can be liberated from the hydrochloride and can be converted into other pharmaceutically acceptable acid addition salts.

Pyrazole compounds, insecticidal and acaricidal compositions and use

There are disclosed a pyrazole compound represented by the formula, STR1 wherein the substituents of R1 to R8 and the symbol Z have the specified meanings as described in the text, an insecticidal and acaricidal composition containing the same, use of said composition for control of insects and mites and a method of preparing said compound, and its intermediate.

Intermediate compounds for an insecticidal and acaricidal pyrazole compound

There are disclosed intermediate compounds of the formula, STR1 wherein the substitutents of R1 to R7 and R9 have the same meanings as described in the text, for producing a insecticidal and acaricidal pyrazole compound represented by the formula, STR2 wherein the substituents of R1 ' to R8 and the symbol Z have the specified meanings as described in the text.