168104-54-9

Basic information

• Product Name: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetate
• Synonyms: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetate
• CAS NO: 168104-54-9
• Molecular Weight: 474.616
• Mol File: 168104-54-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetate(168104-54-9)
• EPA Substance Registry System: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetate(168104-54-9)

Safety Data

• Hazardous Substances Data: 168104-54-9(Hazardous Substances Data)

Upstream product

• 168104-52-7 (S)-Hydroxy-(4-hydroxymethyl-phenyl)-phenyl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 107556-40-1 <4-<<(tert-butyldimethylsilyl)oxy>methyl>phenyl>magnesium bromide 
• 88002-15-7 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 168104-53-8 (S)-Hydroxy-(4-methanesulfonyloxymethyl-phenyl)-phenyl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 168104-56-1 (S)-α-hydroxy-α-<4-(fluoromethyl)phenyl>benzeneacetic acid 

Relevant articles and documents

Syntheses and biological properties of chiral fluoroalkyl quinuclidinyl benzilates

Previously, (R)-quinuclidinyl (R)-4-iodobenzilate ((R,R)-IQNB), a muscarinic receptor antagonist, has been labeled with 123I and 125I for use in in vitro and in vivo studies in animals and humans. We have prepared fluoroalkyl analogs of QNB, which are amenable to labeling with 18F, for potential imaging applications with positron emission tomography. The enantiomers of (fluoroalkyl)benzilic acids were prepared via an enantioselective Grignard addition reaction. Subsequent coupling of the enantiomeric (fluoroalkyl)benzilic acid with a selected enantiomer of quinuclidinol provides fluorinated analogs of QNB with known stereochemistry at each of the stereogenic centers. These compounds exhibit different affinities for the muscarinic receptor tissue subtypes in vitro. (R,R)-4- (Fluoromethyl)-QNB, (R,R)-IQNB, and (R,R)-4-(fluoroethyl)-QNB exhibit selectivity for the M1 subtype, and (R,S)-4-(fluoromethyl)-QNB exhibits selectivity for the M2 subtype.