70913-79-0

Basic information

• Product Name: 2,4-Methanoazulene,decahydro-5,5,8a-trimethyl-1-methylene-, (2R,3aR,4S,8aS)- (9CI)
• Synonyms: 2,4-Methanoazulene,decahydro-5,5,8a-trimethyl-1-methylene-, [2R-(2a,3ab,4a,8ab)]-; Neolongifolene
• CAS NO: 70913-79-0
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Mol File: 70913-79-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,4-Methanoazulene,decahydro-5,5,8a-trimethyl-1-methylene-, (2R,3aR,4S,8aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Methanoazulene,decahydro-5,5,8a-trimethyl-1-methylene-, (2R,3aR,4S,8aS)- (9CI)(70913-79-0)
• EPA Substance Registry System: 2,4-Methanoazulene,decahydro-5,5,8a-trimethyl-1-methylene-, (2R,3aR,4S,8aS)- (9CI)(70913-79-0)

Safety Data

• Hazardous Substances Data: 70913-79-0(Hazardous Substances Data)

Usage

Class

Azulene derivatives

Molecular structure

Bicyclic compound with a fused cyclopropane ring

Chemical and physical properties

Unique properties valuable for various applications in organic chemistry

Stereochemistry

(2R,3aR,4S,8aS) configuration determines reactivity and potential effects

Potential uses

Pharmaceuticals, fragrances, industrial applications

Need for further research

To fully understand properties and uses

Upstream product

• 103864-76-2 Longicamphor tosylhydrazone 

Downstream Products

• 1135-66-6 (-)-isolongifolene 

Relevant articles and documents

Base-induced Thermal Decomposition of Terpenoid Tosylhydrazones: Part I - Chemistry of Diazolongibornanes

The elusive progenitor neolongifolene (6) of Isolongifolene (2) has been synthesized (44percent yield) from longicamphor tosylhydrazone (8) by generating the crucial longibornyl-10-cation (5) under basic conditions in a protic (sodium-ethylene glycol) Bamford-Stevens reaction; Longicyclene (13, 15percent) and the ether-carbinol(14, 16percent) are the other products.Exposure of 6 to BF3.OEt2 in benzene transforms it to 2.Under aprotic conditions (sodium methoxide-diglyme) 8 gives longicyclene (13) as the major product (41percent) with a trace (5percent) of 6.When 8 is exposed to n-butyllithium in hexane, the novel longibornylene (21) (54percent) is formed.Generation of anelectron-deficient species at the C-4 position on the longibornane skeleton via 24->25->26 has been studied: a novel transannular carbene insertion product 30 is formed from 24 under aprotic conditions only .In this reaction olefins 27 and 28 are very minor (5percent); the major crystalline compound is the 4-oxolongibornane azine (31) (ca. 30percent).Refluxing 24 in ethylene glycol with the sodium salt of ethylene glycol yields 27 (15percent) and 28 (16percent), besides the oxygenated compound 29 (19percent).