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

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

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

Downstream Products

• 112046-83-0 allophanic acid-(1-prop-2-ynyl-cyclopentyl ester) 
• 40485-29-8 4-(1-hydroxy-cyclopentyl)-1-phenyl-but-2-yn-1-one 
• 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) 

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.

Regioselective access to CF3S-substituted dihydrofurans from homopropargylic alcohols with trifluoromethanesulfenamide

A facile access to 4-((trifluoromethyl)thio)-2,3-dihydrofurans from unprotected homopropargylic alcohols in high regioselectivity is reported. This method is the first example of using a free hydroxy group as a nucleophile to complete a trifluoromethylthiolation/cyclization protocol with an alkyne in moderate to excellent yields. This journal is

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.

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.

Preparation of 5-membered rings via radical addition-translocation- cyclization (RATC) processes mediated by diethyl thiophosphites

A practical method for the formation of thiophosphonates bearing functionalized monocyclic, fused bicyclic and spirocyclic residues is presented. The procedure requires the easily available terminal alkynes as starting materials as well as commercially an

INHIBITORS OF DIACYLGLYCEROL O-ACYLTRANSFERASE TYPE 1 ENZYME

The present invention relates to compounds of formula (I): wherein R1, R2, and R3, are defined herein. Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.

Preparation of homoallylic homopropargylic alcohols from 2-vinyloxiranes

(Chemical Equation Presented) β,γ-Unsaturated aldehydes generated in situ by treatment of 2-vinyloxiranes with a catalytic amount of Sc(OTf)3 or BF·OEt2 are effectively trapped by B-allenyl-9-BBN to afford homoallylic homopropargylic alcohols in high yield. An enantioselective version has been demonstrated, and a convenient synthesis of 9-allenyl-9-BBN is described.

A new method for the preparation of 1,3-dilithiopropyne: An efficient synthesis of homopropargyl alcohols

Controlled dilithiation of propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with aldehydes and ketones to produce homo

Propargylation of carbonyl compounds: An efficient method for the synthesis of homopropargyl alcohols

Controlled dilithiation of allene, with two equivalents of n- butyllithium, produces the propargyl dianion 5. The latter couples efficiently with carbonyl compounds to produce homopropargyl alcohol in high yields.