31061-64-0

Basic information

• Product Name: Tricyclo[4.3.1.13,8]undecan-1-ol
• Synonyms: 1-Hydroxyhomoadamantane;Tricyclo[4.3.1.13,8]undecan-1-ol
• CAS NO: 31061-64-0
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.26002
• Mol File: 31061-64-0.mol

Chemical Properties

• Boiling Point: 263.7°Cat760mmHg
• Flash Point: 109.4°C
• Appearance: /
• Density: 1.116g/cm³
• Vapor Pressure: 0.00142mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: Tricyclo[4.3.1.13,8]undecan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Tricyclo[4.3.1.13,8]undecan-1-ol(31061-64-0)
• EPA Substance Registry System: Tricyclo[4.3.1.13,8]undecan-1-ol(31061-64-0)

Safety Data

• Hazardous Substances Data: 31061-64-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H18O/c12-11-5-8-1-2-9(6-11)4-10(3-8)7-11/h8-10,12H,1-7H2

Upstream product

• 281-46-9 homoadamantane 
• 31083-61-1 1-Amino-homoadamantan 
• 281-46-9 homoadamantane 

Downstream Products

• 21898-95-3 1-methoxyhomoadamantane 

Relevant articles and documents

Relative Reactivity of Bridgehead Adamantyl and Homoadamantyl Substrates from Solvolyses with Heptafluorobutyrate as a Highly Reactive Carboxylate Leaving Group. Absence of SN2 Character of Solvolysis of tert-Butyl Derivatives

Heptafluorobutyrates, conveniently prepared from alcohols, possess a reactivity similar to that of halides in solvolysis reactions.A product and isotope distribution study for the reaction of 1-adamantyl heptafluorobutyrate (1a) in 80:20 ethanol-H2(18)O demonstrated exclusive alkyl-oxygen cleavage.The reactivities of 1a, 1-(2a), and 3-homoadamantyl heptafluorobutyrate (3a) increase with the flexibility of the hydrocarbon skeleton.The rate constants are linearly correlated with the strain increase upon ionization.No acceleration attributable to nucleophilic solvent assistance was evidenced for the tert-butyl ester, 4a.A literature proposal for such assistance in solvolyses of 4 is examined.The existing data are explained better by an SN1 process with electrophilic assistance of the leaving group in the solvents that can form very strong hydrogen bonds.

Competitive and Regiospecific Bridgehead Substitution in Electrophilic Oxidation Reactions of Homoadamantane

Oxidation of homoadamantane with chromic acid, lead tetraacetate, p-nitroperbenzoic acid, or bromine occurs by competitive attack at the C-3 (major) and C-1 (minor) bridgehead positions.In striking contrast, dry ozonation of homoadamantane adsorbed on silica gel leads to regiospecific substitution at the chemically equivalent C-3 and C-6 bridgehead positions.A consequence of this observation is that some 1,3- and 3,6-disubstituted homoadamantanes can be prepared by dry ozonation of suitably substituted homoadamantane derivatives.

The Isomerisation of Homoadamantane-3-carboxylic Acid into Homoadamantane-1-carboxylic Acid

It is shown by D-, 13C-, and double labelling experiments that the title isomerisation 2 -> 3 under Koch-Haaf conditions is due to reversible decarbonylation followed by intermolecular hydride transfer between the bridgehead positions of the two bridgehead homoadamantane cations and homoadamantane derivatives.The isomerisation is accompanied by complete equilibration of an isotopically labelled methylene group over all possible positions.This is due to the known adamantylmethyl-3-homoadamantyl cation rearrangement which is likewise occuring.In contrast to hydride transfer reactions in the adamantyl system the methylene groups of the homoadamantyl system are not participating in the hydride transfer between the bridgehead positions.