487-73-0

Basic information

• Product Name: (1S,3aα,8aα,9R)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carboxylic acid
• Synonyms: (1S,3aα,8aα,9R)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carboxylic acid
• CAS NO: 487-73-0
• Molecular Formula: C15H24O2
• Molecular Weight: 236.35
• Mol File: 487-73-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,3aα,8aα,9R)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3aα,8aα,9R)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carboxylic acid(487-73-0)
• EPA Substance Registry System: (1S,3aα,8aα,9R)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carboxylic acid(487-73-0)

Safety Data

• Hazardous Substances Data: 487-73-0(Hazardous Substances Data)

Upstream product

• 475-20-7 (+)-Longifolen 
• 475-20-7 longifolene 
• 19067-29-9 longifolene 
• 469-27-2 Isolongifolol 
• 13928-57-9 (7R)-longifolanoic acid-⁽¹⁵⁾-methyl ester 

Relevant articles and documents

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The ozonolysis of longifolene: A tool for the preparation of useful chiral compounds. Configuration determination of new stereogenic centers by NMR spectroscopy and X-ray crystallography

The ozonolysis of (+)-longifolene (1) in different solvents (Et2O, CH2Cl2, CHCl3, acetone) at -80° provided quantitatively longifolene epoxide (3) as a single diastereoisomer in which the O-atom is endopositioned (Scheme 2). Upon warming to room temperature, the epoxide remained stable only in acetone and was isolated as a low-melting crystalline compound. In CH2Cl2, Et2O, or CHCl3 solution, epoxide 3 rapidly rearranged to the isomeric enols 4 and 5, which underwent further rearrangement to give the exo-aldehyde 6. On standing for several weeks in CH2Cl2 solution, or in CHCl3 and Et2O as well, at room temperature, aldehyde 6 slowly rearranged into its epimer 7. The aldehydes 6 and 7 were isolated on the preparative scale for further synthetic use. The addition of methylmagnesium iodide to 6 and 7 provided the corresponding alcohols 13/14 and 15/16. respectively, which were isolated as pure diastereoisomers (Scheme 4). The configurations of the new chiral centers in 13-16 were determined by NMR methods and X-ray crystallography.

A Convenient One-pot Hydroboration / Isomerization / Oxidation of Longifolene to Isolongifolol

A convenient one-pot hydroboration / isomerization / oxidation of longifolene (1) to the thermodynamically more stable epimer, isolongifolol (3) is described.Furthermore, a practical in situ method for the hydroboration of 1 in THF, has been optimised to generate the less stable epimer, longifolol (2).