173200-56-1

Basic information

• Product Name: 1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne
• Synonyms: 1-Hydroxy-6,6-dimethyl-2-hepten-4-yne;(E)-6,6-DIMETHYLHEPT-2-EN-4-YN-1-OL;Terbinafine Related Compound 4
• CAS NO: 173200-56-1
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.20686
• Mol File: 173200-56-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne(173200-56-1)
• EPA Substance Registry System: 1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne(173200-56-1)

Safety Data

• Hazardous Substances Data: 173200-56-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne is used as an intermediate in the synthesis of N-Desmethyl Terbinafine (D294300), a metabolite of Terbinafine. Terbinafine is an orally active, antimycotic allylamine related to naftifine, which is used to treat various fungal infections. The compound plays a crucial role in the development of new antimycotic drugs, contributing to the fight against fungal diseases.

Upstream product

• 52323-98-5 4,4-dimethylpent-2-yn-1-ol 
• 78629-21-7 (E)-6,6-dimethyl-2-hepten-4-ynyl bromide 
• 126764-15-6 (E/Z)-1-bromo-6,6-dimethylhept-2-ene-4-yne 
• 54599-49-4 ethyl 6,6-dimethyl-2-hepten-4-ynoate 

Relevant articles and documents

Chemo-, regio-, and stereoselective hydroboration of conjugated enyne alcohol/amine: Facile synthesis of Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group

Hydroboration of conjugated enyne alcohol/amine is studied by using copper salts and bis(pinacolato)diboron as pre-catalysts and boron source respectively. It is suggested that the chemo-selectivity is derived from a combined electronic influence of the heteroatoms on the substrate and the ligand on the transition metal. The regioselectivity is probably dominated mainly by electronic effect of the alkyne substituent. This study resulted in a highly selective protocol to access Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group.

Identification of a reactive metabolite of terbinafine: Insights into terbinafine-induced hepatotoxicity

Oral terbinafine treatment for superficial fungal infections of toe and fingernails is associated with a low incidence (1:45000) of hepatobiliary dysfunction. Due to the rare and unpredictable nature of this adverse drug reaction, the mechanism of toxicity has been hypothesized to be either an uncommon immunological or metabolically mediated effect. However, there is little evidence to support either mechanism, and toxic metabolites of terbinafine have not been identified. We incubated terbinafine with both rat and human liver microsomal protein in the presence of GSH and were able to trap an allylic aldehyde, 7,7-dimethylhept-2-ene-4-ynal (TBF-A), which corresponds to the N-dealkylation product of terbinafine. TBF-A was also prepared synthetically and reacted with excess GSH to yield conjugates with HPLC retention times and mass spectra identical to those generated in the microsomal incubations. The major GSH conjugate, characterized by 1H NMR, corresponds to addition of GSH in a 1,6-Michael fashion. There remains a second electrophilic site on this metabolite, which can bind either to a second molecule of GSH or to cellular proteins via a 1,4-Michael addition mechanism. Moreover, we demonstrated that the formation of the GSH conjugates was reversible. We speculate that this allylic aldehyde metabolite, formed by liver enzymes and conjugated with GSH, would be transported across the canalicular membrane of hepatocytes and concentrated in the bile. The mono-GSH conjugate, which is still reactive, could bind to hepatobiliary proteins and lead to direct toxicity. Alternatively, it could modify canalicular proteins and lead to an immune-mediated reaction causing cholestatic dysfunction.

Synthesis of vinylallenes by conjugate 1,6-, 1,8-, 1,10- and 1,12-addition reactions of organocuprates with acetylenic Michael acceptors and their use as dienes in intermolecular Diels-Alder reactions

Various vinylallenes were synthesized by conjugate cuprate additions to acetylenic Michael acceptors. Thus, 1,6-addition reactions with 2-en-4-ynoates 1, 3, and 5a, respectively, furnished vinylallenes 2, 4, and 7 after regioselective electrophilic capture of the allenyl enolates formed. Likewise, 1,8-addition to 2,4-dien-6-ynoates 8a and 10 gave the vinylallenes 9 and 11, whereas the 1,10-addition of Me2CuLi to 2,4,6-trien-8-ynoate 12 provided allene 13, and the analogous 1,12-addition to 2,4,6,8-tetraen-10-ynoate 14 furnished the polyene 15. These vinylallenes are valuable dienophiles in regio- and stereoselective Diels-Alder reactions, as evidenced by the formation of the cycloaddition products 16-24. In the presence of Lewis acids, vinylallene 4a presumably rearranges to a cyclopentadiene derivative which then forms the cycloadducts 25 and 26. VCH Verlagsgesellschaft mbH, 1996.

Antifungal derivatives of N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine and method of using same

N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine derivatives are provided having the general formula STR1 wherein R1 is methoxy, iminomethyl or 1-iminoethyl and R2 and R3 are each hydrogen; or R1 is methyl and one of R2 and R3 is hydrogen and the other is halogen. The above compounds as well as acid-addition salts thereof are useful as antifungal agents.