90925-09-0

Basic information

• Product Name: Cyclopentanol, 1-(3-methyl-3-buten-1-ynyl)- (7CI,9CI)
• Synonyms: Cyclopentanol, 1-(3-methyl-3-buten-1-ynyl)- (7CI,9CI)
• CAS NO: 90925-09-0
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• Mol File: 90925-09-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentanol, 1-(3-methyl-3-buten-1-ynyl)- (7CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanol, 1-(3-methyl-3-buten-1-ynyl)- (7CI,9CI)(90925-09-0)
• EPA Substance Registry System: Cyclopentanol, 1-(3-methyl-3-buten-1-ynyl)- (7CI,9CI)(90925-09-0)

Safety Data

• Hazardous Substances Data: 90925-09-0(Hazardous Substances Data)

Upstream product

• 120-92-3 cyclopentanone 
• 78-80-8 2-methylbut-1-en-3-yne 
• 38341-85-4 (3-methyl-but-3-en-1-ynyl)-lithium 

Downstream Products

• 1313867-28-5 1-benzyloxy-1-(3-methylbut-3-en-1-ynyl)-cyclopentane 
• 1313867-50-3 4-methyl-N-(2-methyl-3-(spiro[cyclopentane-1,3'-isochroman]-4'-ylidene)allyl)benzenesulfonamide 
• 1313867-37-6 2-((1-(benzyloxy)cyclopentyl)ethynyl)-2-methyl-1-tosylaziridine 
• 158530-50-8 spiro-methyl-5'-oxa-2'-phenylsulfinyl-2',2-cyclohexeneone> 
• 158530-39-3 (2-phenylsulfinyl-3-methyl-1,3-butadienylidene)cyclopentane 

Relevant articles and documents

C-H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes

gem-Hydrogenation of an internal alkyne with the aid of [Cp*RuCl]4 as the precatalyst is a highly unorthodox transformation, in which one C atom of the triple bond is transformed into a methylene group, whereas the second C atom gets converted into a ruthenium carbene. In the case of 1,3-enynes bearing a propargylic steering substituent as the substrates, the reaction occurs regioselectively, giving rise to vinyl carbene complexes that adopt interconverting η1/η3-binding modes in solution; a prototypical example of such a reactive intermediate was characterized in detail by spectroscopic means. Although both forms are similarly stable, only the η3-vinyl carbene proved kinetically competent to insert into primary, secondary, or tertiary C-H bonds on the steering group itself or another suitably placed ether, acetal, orthoester, or (sulfon)amide substituent. The ensuing net hydrogenative C-H insertion reaction is highly enabling in that it gives ready access to spirocyclic as well as bridged ring systems of immediate relevance as building blocks for medicinal chemistry. Moreover, the reaction scales well and lends itself to the formation of partly or fully deuterated isotopologues. Labeling experiments in combination with PHIP NMR spectroscopy (PHIP = parahydrogen induced polarization) confirmed that the reactions are indeed triggered by gem-hydrogenation, whereas kinetic data provided valuable insights into the very nature of the turnover-limiting transition state of the actual C-H insertion step.

Gold(i)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]

Alkynylaziridines carrying an aryl group could be efficiently converted to spiro[isochroman-4,2′-pyrrolines] with gold salts as catalysts. This new rearrangement involved a Friedel-Crafts type intramolecular reaction followed by cyclization of the aminoallene intermediate, both initiated by the dual σ and π Lewis acidities of gold.

The Intramolecular Enyne Diels-Alder Reaction. Stereoselective Construction of Tricyclic Dioxadienones and Mechanistic Outline

4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H-pyran-3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.