287471-30-1 Usage
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 287471-30-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,7,4,7 and 1 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 287471-30:
(8*2)+(7*8)+(6*7)+(5*4)+(4*7)+(3*1)+(2*3)+(1*0)=171
171 % 10 = 1
So 287471-30-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H13Cl/c1-9(2,3)7-5-4-6-8-10/h4,6H,8H2,1-3H3/b6-4+
287471-30-1Relevant articles and documents
A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: A key intermediate for terbinafine
Chou, Shan-Yen,Tseng, Chin-Lu,Chen, Shyh-Fong
, p. 3895 - 3898 (2000)
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.
Process for the preparation of terbinafine and salts thereof
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Page/Page column 8; 10, (2008/06/13)
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.
Pyrazole compounds, insecticidal and acaricidal compositions and use
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, (2008/06/13)
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.
