169555-85-5

Basic information

• Product Name: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2-oxo-1-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexyl ester
• Synonyms: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2-oxo-1-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexyl ester
• CAS NO: 169555-85-5
• Molecular Weight: 404.579
• Mol File: 169555-85-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2-oxo-1-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2-oxo-1-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexyl ester(169555-85-5)
• EPA Substance Registry System: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2-oxo-1-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexyl ester(169555-85-5)

Safety Data

• Hazardous Substances Data: 169555-85-5(Hazardous Substances Data)

Upstream product

• 765-87-7 cyclohexane-1,2-dione 
• 51128-50-8 2-[(trimethylsilyl)oxy]cyclohex-2-en-1-one 
• 39637-74-6 (1S)-(-)-camphanic chloride 
• 128939-10-6 2-hydroxy-2-(3-trimethylsilylprop-2-ynyl)cyclohexanone 

Downstream Products

• 169555-86-6 (+)-2-hydroxy-2-(3-trimethylsilylprop-2-ynyl)cyclohexanone 

Relevant articles and documents

Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications

In refluxing diglyme, rearrangement of α-hydroxy imines bearing diversely substituted allyl groups or a 3-trimethylsilylpropargyl group on the α-carbon to the nitrogen afforded in good yields α-amino ketones. Migration of allyl or 3-trimethylsilylallyl groups occurred without allylic transposition in contrast to be 1-methylallyl group. In the 3 cases studied, the rearrangement of enantioenriched α-hydroxy imines took place with complete 1,2-chirality transfer. The rearrangement was applied to the preparation of (+)-1-benzyl-1-azaspiro[5.5]undecan-7-one, a precursor in the synthesis of (-)-perhydrohistrionicotoxin.