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
• Article Data: 4

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

Description

1-Hydroxy-6,6-Dimethyl-2-Heptene-4-Yne, also known as (E)-6,6-Dimethylhept-2-en-4-yn-1-ol, is an organic compound with a unique structure featuring a hydroxyl group, two methyl groups, and a heptene-4-yne backbone. It is characterized by its molecular formula C9H14O and is an important intermediate in the synthesis of various pharmaceutical compounds.

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

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

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.

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.