178243-92-0

Basic information

• Product Name: Cyclohexane, 2-ethynyl-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI)
• Synonyms: Cyclohexane, 2-ethynyl-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI)
• CAS NO: 178243-92-0
• Molecular Formula: C12H20
• Molecular Weight: 164.2872
• Product Categories: ISOPROPYL
• Mol File: 178243-92-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexane, 2-ethynyl-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexane, 2-ethynyl-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI)(178243-92-0)
• EPA Substance Registry System: Cyclohexane, 2-ethynyl-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI)(178243-92-0)

Safety Data

• Hazardous Substances Data: 178243-92-0(Hazardous Substances Data)

Relevant articles and documents

Enantiospecific Alkynylation of Alkylboronic Esters

Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves use of α-lithio vinyl bromide or vinyl carbamate species, for which application to Zweifel-type reactions has not previously been explored. The resulting functionalized 1,1-disubstituted alkenes undergo facile base-mediated elimination to generate terminal alkyne products in high yield and excellent levels of enantiospecificity over a wide range of pinacolboronic ester substrates. Furthermore, along with terminal alkynes, internal and silyl-protected alkynes can be formed by simply introducing a suitable carbon- or silicon-based electrophile after the base-mediated 1,2-elimination reaction. Enantiospecific alkynylation: Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction to give alkynes in high yield and essentially complete enantiospecificity.

Stereogenic propargylic centers via base-mediated terminal allne isomerization

A study of alkali metal amide-mediated isomerizations of terminal allenes is described. The isomerizations of substituted ethenylidenecyclohexanes to form diastereomeric mixtures of terminal alkynes have been conducted to determine factors which may influence the stereochemistry at the newly formed propargylic centers. An initial base screen revealed that potassium N-methylbutylamide (KMBA) exhibits the highest level of equatorial to axial alkyne diastereoselectivity. With the severely hindered terminal allene 26, the use of potassium 3-aminopropylamide is required to effect isomerization. A general synthesis of deuterated terminal allenes has also been achieved, and a mechanistic study using d2-allenes 18a,b has revealed the involvement of a propargylic anion in the course of the KMBA-mediated isomerizations.