165602-45-9

Basic information

• Product Name: O-(8-tert-butyldimethylsilyloxy-5-oxo-6-octynyl) O-phenyl thionocarbonate
• Synonyms: O-(8-tert-butyldimethylsilyloxy-5-oxo-6-octynyl) O-phenyl thionocarbonate
• CAS NO: 165602-45-9
• Molecular Weight: 406.618
• Mol File: 165602-45-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: O-(8-tert-butyldimethylsilyloxy-5-oxo-6-octynyl) O-phenyl thionocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(8-tert-butyldimethylsilyloxy-5-oxo-6-octynyl) O-phenyl thionocarbonate(165602-45-9)
• EPA Substance Registry System: O-(8-tert-butyldimethylsilyloxy-5-oxo-6-octynyl) O-phenyl thionocarbonate(165602-45-9)

Safety Data

• Hazardous Substances Data: 165602-45-9(Hazardous Substances Data)

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 91509-32-9 3-(t-butyldimethylsilyloxy)prop-1-ynyllithium 
• 1005-56-7 phenylcarbonochloridothioate 

Downstream Products

• 165602-46-0 O-(8-tert-butyldimethylsilyloxy-5-hydroxy-6-octynyl) O-phenyl thionocarbonate 

Relevant articles and documents

Sigmatropic Ring Expansion of Cyclic Thionocarbonates. 13. Synthesis of Medium-Membered Heterocyclic Allenes and Synthetic Application to Antifungal Constituent of Sapium Japonicum

Cyclic allenes (3a-k, 3n) containing a SCOO moiety in the range of 8- to 11-membered ring were synthesized by the sigmatropic rearrangement of the alkynyl cyclic thionocarbonates (2).Ring expansion of 6-membered cyclic thionocarbonates (2i-k) afforded a new type of strained 8-membered heterocyclic allenes (3i-k) in high yields.The MNDO optimized structure of 3i indicated the allenyl moiety was bent and strained.The reactivity of 8-membered cyclic allenes was also examined.Further, using this methodology with a novel application of a SmI2-HMPA reduction of resulting heterocyclic allene (3n), an antifungal constituent of a Sapium japonicum, (+/-)-methyl 8-hydroxy-5,6-octadienoate (24), was synthesized.