24469-57-6

Basic information

• Product Name: Cycloundecanol
• Synonyms: Cycloundecanol
• CAS NO: 24469-57-6
• Molecular Formula: C₁₁H₂₂O
• Molecular Weight: 170.29
• Mol File: 24469-57-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cycloundecanol(CAS DataBase Reference)
• NIST Chemistry Reference: Cycloundecanol(24469-57-6)
• EPA Substance Registry System: Cycloundecanol(24469-57-6)

Safety Data

• Hazardous Substances Data: 24469-57-6(Hazardous Substances Data)

Upstream product

• 57620-93-6 2-Hydroxy-1-cycloundecanon 
• 109701-92-0 Isobutyric acid cycloundecyl ester 
• 78052-04-7 toluene-4-sulfonic acid cycloundecyl ester 
• 878-13-7 cycloundecanone 

Downstream Products

• 878-13-7 cycloundecanone 
• 3246-80-8 9-phenyl-9H-xanthene 
• 1361407-99-9 C₁₈H₂₇NO 
• 78052-04-7 toluene-4-sulfonic acid cycloundecyl ester 
• 91459-01-7 Cycloundecyl-acetat 
• 13151-60-5 trans-cycloundecane 
• 502-41-0 cycloheptanol 

Relevant articles and documents

A Catalytic Model for the Dioldehydratase Reaction

The diastereoisomeric 6,7-dihydroxycycloundecyl iodides (3a), (3b), and (3c) have been synthesised; their conversion into cycloundecanone (12) in the presence of sodium borohydride and traces of cobalt complexes provides the first catalytic model for the coenzyme B12 catalysed dioldehydratase reaction.

Structure-reactivity relationship for alcohol oxidations via hydride transfer to a carbocationic oxidizing agent

Second-order rate constants were determined for the oxidation of 27 alcohols (R1R2CHOH) by a carbocationic oxidizing agent, 9-phenylxanthylium ion, in acetontrile at 60°C. Alcohols include open-chain alkyl, cycloalkyl, and unsaturated alcohols. Kinetic isotope effects for the reaction of 1-phenylethanol were determined at three H/D positions of the alcohol (KIEα-D=3.9, KIEβ-D3=1.03, KIE OD=1.10). These KIE results are consistent with those we previously reported for the 2-propanol reaction, suggesting that these reactions follow a hydride-proton sequential transfer mechanism that involves a rate-limiting formation of the α-hydroxy carbocation intermediate. Structure-reactivity relationship for alcohol oxidations was deeply discussed on the basis of the observed structural effects on the formation of the carbocationic transition state (Cδ+-OH). Efficiencies of alcohol oxidations are largely dependent upon the alcohol structures. Steric hindrance effect and ring strain relief effect win over the electronic effect in determining the rates of the oxidations of open-chain alkyl and cycloalkyl alcohols. Unhindered secondary alkyl alcohols would be selectively oxidized in the presence of primary and hindered secondary alkyl alcohols. Strained C7-C11 cycloalkyl alcohols react faster than cyclohexyl alcohol, whereas the strained C5 and C12 alcohols react slower. Aromatic alcohols would be efficiently and selectively oxidized in the presence of aliphatic alcohols of comparable steric requirements. This structure-reactivity relationship for alcohol oxidations via hydride-transfer mechanism is hoped to provide a useful guidance for the selective oxidation of certain alcohol functional groups in organic synthesis. Copyright

β'β ANIONIC ELIMINATION OF CARBOXYLIC ESTERS

The elimination of lithium, magnesium and aluminium enolates of isobutyrates of medium ring cyclanols occurs in a syn fashion.A set of experimental procedures is presented.This elimination seems to be restricted to strained systems.The stereochemistry has been determined on stereospecifically deuterated cyclooctanol isobutyrates.The primary isotope effect kH/k2 was 3.0 +/- 0.1 and the secondary 1.1.The name β'β elimination is proposed for this syn elimination and related elimination.