3859-35-6

Basic information

• Product Name: 1-ethenylcyclopentanol
• CAS NO: 3859-35-6
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.1696
• Mol File: 3859-35-6.mol

Chemical Properties

• Boiling Point: 157.7°C at 760 mmHg
• Flash Point: 58.1°C
• Density: 1.068g/cm³
• Vapor Pressure: 0.973mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 1-ethenylcyclopentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethenylcyclopentanol(3859-35-6)
• EPA Substance Registry System: 1-ethenylcyclopentanol(3859-35-6)

Safety Data

• Hazardous Substances Data: 3859-35-6(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Classification

Vinyl alcohol

Structure

Cyclopentane ring with a vinyl group (C=C) and a hydroxyl group (OH) attached

Common uses

Synthesis of other organic compounds

Applications

Building block in production of organic chemicals and pharmaceuticals

Role in synthesis

Reagent in organic synthesis

Industrial use

Intermediate in production of polymers and plastics

Research potential

Applications in the field of organic chemistry research and development

Upstream product

• 28256-63-5 2-methyl-1-oxaspiro<2.4>heptane 
• 3742-34-5 vinylcyclopentane 
• 120-92-3 cyclopentanone 
• 67-56-1 methanol 
• 17356-19-3 1-ethynylcyclopentanol 
• 1826-67-1 vinyl magnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 593-60-2 Vinyl bromide 

Downstream Products

• 96534-89-3 2-(2-Cyclopentyliden-aethyl)-dihydroresorcin 
• 100-47-0 benzonitrile 
• 51679-32-4 2-(phenylthiomethyl)cyclohexanone 
• 87567-39-3 [2-(2-Cyclopentylidene-ethanesulfonyl)-1,1-dimethyl-ethyl]-benzene 
• 502-42-1 cycloheptanone 
• 583-60-8 2-Methylcyclohexanone 
• 73089-99-3 1-[2-(1-Hydroxycyclopentyl)ethyl]cyclohexanol 
• 114694-23-4 1-(2-Phenylsulfanyl-ethyl)-cyclopentanol 
• 4549-20-6 2-methyl cyclohexanone semicarbazone 

Relevant articles and documents

Synthesis of (polyfluoroalkyl)cyclopentenes as model compounds for fluorophilic cyclopentadienes

Nucleophilic opening of the epoxide ring in 6-oxabicyclo[3.1.0]hexane (1) with ethenyl-magnesium bromide was employed for the preparation of 2-ethenylcyclopentan-1-ol (2). Radical addition of perfluoroalkyl iodides 3 to alcohol 2 afforded (polyfluoroiodoalkyl)cyclopentanols 4, which were deiodinated with tributylstannane to (polyfluoroalkyl)-cyclopentanols 5, followed by dehydration with Nafion-H to the target (polyfluoroalkyl)-cyclopentenes 6, which are potential intermediates for fluorous chemistry. Attempts to synthesize (polyfluoroalkyl)cyclopentadienes or bis(polyfluoroalkyl)cyclopentadienes failed due to the exclusive formation of unexpected side product, polyfluoroiodoalkanol 7, in the course of radical addition of perfluoroalkyl iodides 3 to ethenylcyclopentenol (8) or diethenylcyclopentanediol (9), respectively.

Photoinduced Cross-Coupling of Aryl Iodides with Alkenes

A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes has been developed. The radical cascade mechanism involving generation of aryl radicals via C-I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes is proposed. The method enables iodide-selective cross-coupling over other halogen leaving groups with functional group compatibility on both arene and alkene motifs.

Accessing Frustrated Lewis Pair Chemistry through Robust Gold@N-Doped Carbon for Selective Hydrogenation of Alkynes

Pyrolysis of Au(OAc)3 in the presence of 1,10-phenanthroline over TiO2 furnishes a highly active and selective Au nanoparticle (NP) catalyst embedded in a nitrogen-doped carbon support, Au@N-doped carbon/TiO2 catalyst. Parameters such as pyrolysis temperature, type of support, and nitrogen ligands as well as Au/ligand molar ratios were systematically investigated. Highly selective hydrogenation of numerous structurally diverse alkynes proceeded in moderate to excellent yield under mild conditions. The high selectivity toward the industrially important alkene substrates, functional group tolerance, and the high recyclability makes the catalytic system unique. Both high activity and selectivity are correlated with a frustrated Lewis pairs interface formed by the combination of gold and nitrogen atoms of N-doped carbon that, according to density functional theory calculations, can serve as a basic site to promote the heterolytic activation of H2 under very mild conditions. This "fully heterogeneous" and recyclable gold catalyst makes the selective hydrogenation process environmentally and economically attractive.

Gold-Ligand-Catalyzed Selective Hydrogenation of Alkynes into cis-Alkenes via H2 Heterolytic Activation by Frustrated Lewis Pairs

The selective hydrogenation of alkynes to alkenes is an important synthetic process in the chemical industry. It is commonly accomplished using palladium catalysts that contain surface modifiers, such as lead and silver. Here we report that the adsorption of nitrogen-containing bases on gold nanoparticles results in a frustrated Lewis pair interface that activates H2 heterolytically, allowing an unexpectedly high hydrogenation activity. The so-formed tight-ion pair can be selectively transferred to an alkyne, leading to a cis isomer; this behavior is controlled by electrostatic interactions. Activity correlates with H2 dissociation energy, which depends on the basicity of the ligand and its reorganization on activation of hydrogen. High surface occupation and strong Au atom-ligand interactions might affect the accessibility and stability of the active site, making the activity prediction a multiparameter function. The promotional effect found for nitrogen-containing bases with two heteroatoms was mechanistically described as a strategy to boost gold activity. (Graph Presented).

Organic Compounds

Described are spiroalkyl- and -alkenylketones and esters thereof, a method for their production and fragrance compositions comprising them.

Synthesis of spirocyclic butenolides by ring closing metathesis

Spirocyclic butenolides were efficiently prepared by a ring closing metathesis strategy.

Synthesis of carbo- and heterocyclic aldehydes bearing an adjacent donor group - Ozonolysis versus OsO4/KIO4-oxidation

The synthesis of carbo- and heterocyclic aldehydes bearing an ipso-methoxy group is investigated. The synthetic sequence is based on an initial Grignard addition of an olefin to a cyclic ketone followed by methylation of the resulting tertiary alcohol. The terminal olefin serves as precursor for the aldehyde functionality. Oxidation by ozonolysis turned out to depend significantly on the distance of the donor methoxy group. The observed side reactions could be circumvented by applying a one-pot OsO4 mediated diol formation followed by Malaprade oxidation using KIO4. A series of carbo- and heterocyclic precursors were successfully converted to the title products. Springer-Verlag 2004.

OXAZOLIDINONE AND / OR ISOXAZOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

A compound of the formula (I), or a pharmaceutically-acceptable salt, or in-vivo hydrolysable ester thereof: formula (I) wherein in (I) C is for example formula (D), formula (E), formula (H) wherein A and B are independently selected from (i) formula (J)

Synthesis of spirocyclic butenolides by ring closing metathesis

Spirocyclic butenolides were efficiently prepared by a ring closing metathesis strategy.

Cyclopentylalkyl-nitriles

The present invention provides compounds of formula I wherein R1and R3are independently H or C1-3alkyl, and R2is H, C1-3alkyl, methylene or ethylidene, with the proviso that R1and R2are not simultaneously H; n is 0 or 1; and - - -is a single or a double bond, wherein a maximum of two double bonds are present in the compound. Compounds of formula II are also provided: wherein A is selected from the group of CR4R5OH, CR4R5OC(O)R6, CO2R6, CN and C(O)R4; R1, R3, R4, and R5are independently H or C1-3-alkyl; R2is H, C1-3-alkyl, methylene, or ethylidene; R6is H, C1-3alkyl, C2-4alkenyl, or alkinyl; n is 0 or 1; and - - -is a single or a double bond, wherein a maximum of two double bonds are present. Compositions containing compounds of formulae I and II, as well as methods for imparting fragrance to substrates using such compounds are also provided.