29480-18-0

Basic information

• Product Name: 2-PHENYL-2-ADAMANTANOL
• Synonyms: 2-PHENYL-2-ADAMANTANOL;AKOS BC-0734;Adamantan-2-ol, 2-phenyl-
• CAS NO: 29480-18-0
• Molecular Formula: C₁₆H₂₀O
• Molecular Weight: 228.33
• Product Categories: Adamantane derivatives
• Mol File: 29480-18-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 80℃
• Appearance: /
• Density: 1.147±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 2-PHENYL-2-ADAMANTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2-ADAMANTANOL(29480-18-0)
• EPA Substance Registry System: 2-PHENYL-2-ADAMANTANOL(29480-18-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 29480-18-0(Hazardous Substances Data)

Usage

General Description

2-Phenyl-2-adamantanol is a chemical compound with the molecular formula C22H30O. It is a white solid at room temperature and is insoluble in water but soluble in organic solvents. It is a derivative of adamantane with a phenyl group attached to the carbon 2 position. 2-Phenyl-2-adamantanol is commonly used as a chiral auxiliary in asymmetric synthesis, as well as a building block in organic chemistry. It also exhibits biological activity, particularly as an inhibitor of the enzyme acetylcholinesterase, making it a potential candidate for the development of new drugs for the treatment of Alzheimer's disease and other neurological disorders.

InChI:InChI=1S/C16H20O/c17-16(13-4-2-1-3-5-13)14-7-11-6-12(9-14)10-15(16)8-11/h1-5,11-12,14-15,17H,6-10H2

Upstream product

• 51757-47-2 2,2-Dimethyl-5-(tricyclo<3.3.1.1^3,7>decanylidene)-1,3-dioxane-4,6-dione 
• 281-23-2 adamantane 
• 700-58-3 2-Adamantanone 
• 100-58-3 phenylmagnesium bromide 
• 166540-14-3 trans-5-chloro-2-phenyladamantan-2-ol 
• 591-51-5 phenyllithium 
• 108-90-7 chlorobenzene 
• 133709-17-8 2,2-Dimethyl-5-(2-phenyltricyclo<3.3.1.1^3,7>decan-2-yl)-1,3-dioxane-4,6-dione 
• 29480-21-5 2-chloro-2-phenyladamantane 
• 64-17-5 ethanol 
• 108-86-1 bromobenzene 

Downstream Products

• 700-58-3 2-Adamantanone 
• 21898-84-0 4-oxohomoadamantan-5-one 
• 87840-08-2 3-Adamantyliden-6-(2-phenyl-2-adamantyl)-1,4-cyclohexydien 
• 287173-13-1 2-Phenyl-2-adamantanemethanamine hydrochloride 
• 72094-92-9 2-phenyl(tricyclo[3.3.1.1^3,7]decan)-2-amine 
• 73032-81-2 2-phenyltricyclo[3.3.1.1^3,7]decan-2-amine hydrochloride 
• 233669-11-9 2-phenyl-2-adamantanecarbonitrile 
• 129302-84-7 2-phenyladamantane-2-d 
• 74693-85-9 endo-1-(3-endo-hydroxybicyclo<3.3.1>nonan-7-yl)-1-phenylethanol 
• 74693-87-1 2-oxa-1-adamantyl phenyl ketone 
• 29480-21-5 2-chloro-2-phenyladamantane 
• 33831-38-8 2-bromo-2-phenyladamantane 
• 19066-24-1 2-Phenyladamantane 

Relevant articles and documents

X-Ray Crystal Structure of the 2-Phenyladamant-2-yl Cation

The crystal structure of the Sb2F11 salt of the 2-phenyladamant-2-yl cation, 1*Sb2F11, was determined at 183 K (P21/c, R1 = 0.0652, ?(C-C) = 0.02 Angstroem), because earlier published results indicated a charge delocalization from the cationic

2-Substituted and 2,2-disubstituted adamantane derivatives as models for studying substituent chemical shifts and C-Hax?Yax cyclohexane contacts - results from experimental and theoretical NMR spectroscopic chemical shifts and DFT structures

Abstract The complete 1H and 13C NMR chemical shifts assignment for various 2-substituted and 2,2-disubstituted adamantane derivatives 1-38 in CDCl3 solution was realized on the basis of NMR experiments combined with chemical structure information and DFT-GIAO (B3LYP/6-31+G(d,p)-GIAO) calculations of chemical shifts in solution. Substituent-induced 13C NMR chemical shifts (SCS) are discussed. C-Hax?Yax contacts are a textbook prototype of steric hindrance in organic chemistry. The nature of these contacts will be further investigated in this work on basis of new adamantane derivatives, which are substituted at C-2 to provide models for 1,4-C-Hax?Yax and 1,5-C-Hax?Yax contacts. The B3LYP/6-31+G(d,p) calculations predicted the presence of NBO hyperconjugative attractive interactions between C-Hax and Yax groups along C-Hax?Yax contacts. The 1H NMR signal separation, Δδ(γ-CH2), reflects the strength of the H-bonded C-Haxa?Yax contact.

13C NMR spectroscopic comparison of sterically stabilized meta and para-substituted o-tolyldi(adamant-l-yl)methyl cations with conjugatively stabilized benzyl cations

A series of meta- and para-substituted anti-o-tolyldi(adamant-1-yl)methyl cations has been generated by reaction of anti-o-tolyldi(adamant-1-yl)methanols with trifluoroacetic acid in chloroform. 13C NMR spectroscopy indicates small but significant variations in the chemical shifts of the charged carbon and its nearest neighbours on the adamantyl groups, and departures from additivity of substituent effects on the shifts of the aromatic carbons. Previous work on the closely related di(adamant-1-yl)benzyl cations is discussed. Comparison with data on aryl-substituted carbocations in superacid media reveals marked differences in the aromatic carbon shifts in the two types of carbocation. The dihedral angle between aryl and carbocation planes in aryldi(adamant-1-yl)methyl cations is estimated to be about 60°.