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1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE Structure
CAS No.
287471-30-1
Chemical Name:
1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE
Synonyms
1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE;Terbinafine Impurity 45;Terbinafine Impurity 22;1-Chloro-6,6-dimethyl-2-hepten-4-yne;2-HEPTEN-4-YNE,1-CHLORO-6,6-DIMETHYL;1-Chloro-6,6-dimethyl-2-hepten-4-ino;(E)-1-chloro-6,6-diMethylhept-2-en-4-yne;(2E)-1-chloro-6,6-dimethylhept-2-en-4-yne;1-CHLORO-6,6-DIMETHYL-2-ENE-4-YNE-HEPTANE;2-HEPTEN-4-YNE, 1-CHLORO-6,6-DIMETHYL-, (2E)-
CBNumber:
CB0198486
Molecular Formula:
C9H13Cl
Molecular Weight:
156.65
MOL File:
287471-30-1.mol
MSDS File:
SDS
Modify Date:
2023/12/7 13:00:17

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE Properties

Boiling point 207.5±23.0 °C(Predicted)
Density 0.946±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere, 2-8°C
InChI InChI=1S/C9H13Cl/c1-9(2,3)7-5-4-6-8-10/h4,6H,8H2,1-3H3/b6-4+
InChIKey ZIXABMZBMHDFEZ-GQCTYLIASA-N
SMILES C(Cl)/C=C/C#CC(C)(C)C
CAS DataBase Reference 287471-30-1(CAS DataBase Reference)

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE Chemical Properties,Uses,Production

Description

1-Chloro-6,6-dimethyl-2-hepten-4-yne is the allylamine antifungal agents terbinafine intermediate.1-Chloro-6,6-dimethyl-2-hepten-4-yne choose to inhibit COX-fungal squalene, so that reduction of membrane ergosterol, thus inhibiting the growth of fungi play an inhibitory role; right ergosterol synthesis of precursors and no inhibitory effect on other stages.

Uses

1-Chloro-6,6-dimethyl-2-heptene-4-yne is a hydrocarbon derivative and can be used as a pharmaceutical intermediate.

Application

1-Chloro-6,6-dimethyl-2-hepten-4-yne is a chlorinating agent that has been used to minimise hydrochloric acid by converting it to chloride. It is also used in the chlorination of magnesium and other metals. 1-Chloro-6,6-dimethyl-2-hepten-4-yne has been shown to be an effective antifungal agent against dermatophytes such as Trichophyton rubrum and Microsporum canis. The compound is toxic to humans and animals because it produces acrolein and terbinafine during chlorination. It also produces hydrochloric acid as a by-product of chlorination.

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.Synthesis_287471-30-1

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE Preparation Products And Raw materials

Raw materials

Preparation Products

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2-HEPTEN-4-YNE, 1-CHLORO-6,6-DIMETHYL-, (2E)- 1-CHLORO-6,6-DIMETHYL-2-ENE-4-YNE-HEPTANE 1-Chloro-6,6-dimethyl-2-hepten-4-ino 2-HEPTEN-4-YNE,1-CHLORO-6,6-DIMETHYL 1-Chloro-6,6-dimethyl-2-hepten-4-yne (E)-1-chloro-6,6-diMethylhept-2-en-4-yne (2E)-1-chloro-6,6-dimethylhept-2-en-4-yne Terbinafine Impurity 22 Terbinafine Impurity 45 1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE 287471-30-1 Chemical intermediate for Terbinafine