106540-16-3

Basic information

• Product Name: 7βH-8-Oxoisolongifolane tosylhydrazone
• Synonyms: 7βH-8-Oxoisolongifolane tosylhydrazone
• CAS NO: 106540-16-3
• Molecular Weight: 388.574
• Mol File: 106540-16-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7βH-8-Oxoisolongifolane tosylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 7βH-8-Oxoisolongifolane tosylhydrazone(106540-16-3)
• EPA Substance Registry System: 7βH-8-Oxoisolongifolane tosylhydrazone(106540-16-3)

Safety Data

• Hazardous Substances Data: 106540-16-3(Hazardous Substances Data)

Upstream product

• 103873-45-6 7βH-8-oxoisolongifol-9-ene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 26839-51-0 7αH-8-oxoisolongifolane 
• 26839-72-5 7βH-8-oxoisolongifolane 

Downstream Products

• 1135-66-6 (-)-isolongifolene 
• 1028175-80-5 (2S,4aS,8S,8aR)-1,1,5,5-Tetramethyl-octahydro-2,4a-methano-naphthalen-8-ol 
• 106540-17-4 (2S,4aS,8aR)-1,1,5,5-Tetramethyl-1,3,4,5,6,8a-hexahydro-2H-2,4a-methano-naphthalene 
• 106540-18-5 2-((2S,4aS,8R,8aR)-1,1,5,5-Tetramethyl-octahydro-2,4a-methano-naphthalen-8-yloxy)-ethanol 
• 106540-18-5 2-((2S,4aS,8S,8aR)-1,1,5,5-Tetramethyl-octahydro-2,4a-methano-naphthalen-8-yloxy)-ethanol 

Relevant articles and documents

Base-induced Thermal Decomposition of Terpenoid Tosylhydrazones: Part II - Chemistry of 8-diazoisolongifolane/9-Diazoisolongifolene

7αH-8-Oxoisolongifolane (3) on refluxing with tosylhydrazine in CHCl3 gives the tosylhydrazone (7) of the more stable epimer 7βH-8-oxoisolongifolane (6).Refluxing 7 with NaOMe in diglyme gives the disubstituted olefin (15, 31percent), isolongifolene (2, 23percent) and the unusual alcohol (16, 7percent).Two pure C-8 epimers of the 2-hydroxyethyl ether 17 (27percent)/18 (6percent) are formed in the protic Bamford-Stevens reaction (Na in ethylene glycol) on 7; isolongifolene (2, 20percent) and 15 (13percent) are the other products.Attempted preparation of the tosylhydrazone (10) from 8-oxoisolongifol-9-ene (9) generates only the saturated tosylhydrazone (7) via a concomitant reduction of the the olefinic bond in 9 during the reaction. 9-Diazoisolongifolene (14) generated from the tosylhydrazone (13) under aprotic conditions gives the vinylcarbene-derived olefinic methyl ether epimers (20/21) in a major yield (47percent) while the the diene (19, 6percent) and the crystalline azine (22, 4percent) are also formed.Refluxing 13 with Na in ethylene glycol generates the C-9 ethylene glycol substituted compound (23) (54percent) with only a trace (4percent) of 19.