19135-07-0

Basic information

• Product Name: 1-(prop-2-ynyl)cyclopentanol
• Synonyms: 1-(prop-2-ynyl)cyclopentanol
• CAS NO: 19135-07-0
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18028
• Mol File: 19135-07-0.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(prop-2-ynyl)cyclopentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(prop-2-ynyl)cyclopentanol(19135-07-0)
• EPA Substance Registry System: 1-(prop-2-ynyl)cyclopentanol(19135-07-0)

Safety Data

• Hazardous Substances Data: 19135-07-0(Hazardous Substances Data)

Usage

Structure

Cyclopentanol derivative with a prop-2-ynyl group attached to the cyclopentane ring

Usage

Building block in organic synthesis

Applications

a. Pharmaceuticals and fine chemicals
b. Medicinal chemistry (due to unique structure and properties)
c. Flavors and fragrances production
d. Development of new materials and polymers

Industry

Chemical industry

Value

Versatile nature and potential applications make it a valuable compound

Upstream product

• 106-96-7 propargyl bromide 
• 120-92-3 cyclopentanone 
• 146432-19-1 B-allenyl-9-BBN 
• 463-49-0 1,2-propanediene 
• 18295-60-8 propargyl magnesium bromide 
• 18295-60-8 allenylmagnesium bromide 
• 2936-44-9 allenyl iodide 
• 10024-18-7 bromoallene 

Downstream Products

• 112046-83-0 allophanic acid-(1-prop-2-ynyl-cyclopentyl ester) 
• 14442-31-0 1-(3-phenyl-isoxazol-5-ylmethyl)-cyclopentanol 
• 16741-40-5 Diethylamino-acetic acid 1-prop-2-ynyl-cyclopentyl ester 
• 42512-59-4 1-(4-Hydroxy-4-phenyl-but-2-ynyl)-cyclopentanol 
• 91240-09-4 carbamic acid-(1-prop-2-ynyl-cyclopentyl ester) 
• 40485-29-8 4-(1-hydroxy-cyclopentyl)-1-phenyl-but-2-yn-1-one 

Relevant articles and documents

One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation

A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.

A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols

An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.