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

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE 구조식 이미지
카스 번호:
287471-30-1
상품명:
1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE
동의어(영문):
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
분자식:
C9H13Cl
포뮬러 무게:
156.65
MOL 파일:
287471-30-1.mol

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

끓는 점
207.5±23.0 °C(Predicted)
밀도
0.946±0.06 g/cm3(Predicted)
저장 조건
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 데이터베이스
287471-30-1(CAS DataBase Reference)

안전

1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE C화학적 특성, 용도, 생산

개요

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.

용도

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

주요 응용

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 준비 용품 및 원자재

원자재

준비 용품


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