215321-42-9

Basic information

• Product Name: Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• Synonyms: Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS NO: 215321-42-9
• Molecular Weight: 322.832
• Mol File: 215321-42-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester(215321-42-9)
• EPA Substance Registry System: Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester(215321-42-9)

Safety Data

• Hazardous Substances Data: 215321-42-9(Hazardous Substances Data)

Upstream product

• 79-37-8 oxalyl dichloride 
• 104870-80-6 (1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 

Downstream Products

• 913255-92-2 (-)-(1R)-8-phenylisoneomenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate 
• 913255-91-1 (-)-(1R)-8-phenylisoneomenthyl (1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 
• 129214-96-6 (-)-8-phenylneoisomenthyl glyoxylate 

Relevant articles and documents

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.