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

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

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

Downstream Products

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

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.

Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier

Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.

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

Oxy-phenyl-(phenyl)glycinolamides with heterocyclic substituents

Oxy-phenyl-(phenyl)gycinolamides with heterocyclic substituents are prepared by reaction of the corresponding oxyphenylcarboxylic acids with heterocyclic substituents with phenylglycinol. The new substances are suitable as active compounds in medicaments,

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.

The Predominance and Quantification of Steric Effects in the Solvolysis of Secondary Aliphatic Esters

The solvolysis rates of 35 tosylates in hexafluoroisopropyl alcohol are measured and compared to MM2 calculated strain energies, ΔSI, between weighted sp3 states and the lowest sp2 state.For unhindered (pseudo)equatorially substituted cycloalkyl tosylates a linear correlation, free from ambiguities involved, e.g., with the leaving group simulation, is obtained which shows a sensitivity of m=1.04+/-0.05, indicating an extremely late transition state or limiting behavior.Based on the corresponding equation, it is shown that alkyl substituents in the γ- and in the β-position do not promote significant rate increases, even when there is an antiperiplanar disposition between the leaving group and a migrating β-methyl substituent.Instead, these substituents can lead to substantial ΔG* increase (by up to 5 kcal/mol in comparison to the ΔSI prediction), which is related to steric hindrance of solvation and/or hindrance for elimination. 17-(Tosyloxy)androstanes show extremely large epimeric rate ratios of>30000; these are not due to anchimeric assistance but only to the exceedingly slow reaction of the hindered 17β isomer, whereas the fast reaction of the 17α tosylate (e.g. 200 times higher than cyclopentyl tosylate) is in line with the ΔSI calculation. endo-Bicycloheptane esters show evidence for steric hindrance; exo-norbornyl tosylate has, however, a ΔG* value lower by 4 kcal/mol than predicted. ks/kc values, obtained by rate comparison in 80percent ethanol and 97percent HFIP, vary between 0.5 and 300, mainly as a result of different steric hindrance to rearside nucleophilic subnstitution

MIGRATION APTITUDES OF CYCLIC AND POLYCYCLIC BRIDGEHEAD GROUPS IN THE CRIEGEE REARRANGEMENT

The migration aptitudes of cyclic and polycyclic bridgehead groups in the Criegee Rearrangement support ?-neighbouring group participation by pentacoordinated bonding and vertical charge stabilisation in the migrating group and therefore favour transition state 2b and not 2a.