1137-12-8

Basic information

• Product Name: (+)-LONGICYCLENE
• Synonyms: LONGICYCLENE, (+)-;(1S,2S)-1,2,6,6-TETRAMETHYLTETRACYCLO[8.1.0.0(2.8).0(7.11)]UNDECANE;1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-, [1S-(1alpha,2alpha,3abeta,4alpha,8abeta,9R)]-;1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-, [1S-(1alpha,2alpha,3abeta,4alpha,8abeta,9R*)]-;[1S-(1alpha,2alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-1,5,5,8a-tetramethyl-1,2,4-methenoazulene;LONGICYCLEN;C15 H24, 1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-,;(+)-LONGICYCLENE 95+%
• CAS NO: 1137-12-8
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 214-504-5
• Mol File: 1137-12-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 252-254 °C(lit.)
• Flash Point: 92 °C
• Appearance: /
• Density: 0.937 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0614mmHg at 25°C
• Refractive Index: n20/D 1.493
• BRN: 2039581
• CAS DataBase Reference: (+)-LONGICYCLENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-LONGICYCLENE(1137-12-8)
• EPA Substance Registry System: (+)-LONGICYCLENE(1137-12-8)

Safety Data

• RIDADR: UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous
• WGK Germany: 3
• Hazardous Substances Data: 1137-12-8(Hazardous Substances Data)

Usage

General Description

Longicyclene is the first tetracarbocyclic sesquiterpene isolated from the essential oil of Pinus longifolia, Roxb.

InChI:InChI=1/C15H24/c1-13(2)6-5-7-14(3)9-8-10-12(11(9)13)15(10,14)4/h9-12H,5-8H2,1-4H3

Upstream product

• 65395-71-3 10-oxolongibornane 
• 103864-76-2 Longicamphor tosylhydrazone 
• 33496-00-3 (2R)-1t-bromo-2,5,9,9-tetramethyl-(4at,9at)-decahydro-2r,5-cyclo-benzocycloheptene 
• 61262-66-6 (2R)-1t-iodo-2,5,9,9-tetramethyl-(4at,9at)-decahydro-2r,5-cyclo-benzocycloheptene 
• 60909-27-5 (10S, 11S)-himachala-2,4-diene 
• 475-20-7 longifolene 
• 65395-71-3 longicamphor 
• 475-20-7 longifolene 
• 465-23-6 (2R)-1t-chloro-2,5,9,9-tetramethyl-(4at,9at)-decahydro-2r,5-cyclo-benzocycloheptene 

Downstream Products

• 84029-99-2 1,1-Dimethyl-7-t-butylnaphthalene 
• 20051-72-3 C₁₅H₂₄O 
• 63025-62-7 (1R,2R,3aR,4S,8aS)-4,8,8-Trimethyl-9-methylene-decahydro-2,4-methano-azulen-1-ol 
• 64854-50-8 4-Hydroxylongifolene 
• 65395-71-3 longicamphor 
• 20051-72-3 Pseudolongifolol 
• 64854-50-8 4,8,8-Trimethyl-9-methylene-decahydro-1,4-methano-azulen-2-ol 

Relevant articles and documents

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NEW SESQUITERPENOIDS FROM THE OLEORESIN OF Abies alba

The structures of four new sesquiterpenoids from the oleoresin of Abies alba have been studied, On the basis of various spectral characteristics, the structures of (10S, 11S)-himachala-2,4-diene, (10S, 11S)-himachala-3(12),4-diene, humula-4,9-dien-8-ol, and (4S, 5S, 10S)-selina-6-en-4-ol have been proposed for the compounds isolated.The stereochemistry of the assymetric centers was determined by the conversion of these compounds into known sesquiterpenes and also by analysis of PMR spectra with a shift reagent.

A SYNTHESIS OF CULMORIN FROM LONGIFOLENE VIA 8,11-DIBROMO-LONGIBORNANE

A 10-step synthesis of culmorin (XII) from longifolene (I), which involves the formation of 8,11-dibromo-longibornane (VII) as the key intermediate from longicyclene (III), is described.

STABLE CARBOCATIONS FROM TERPENOIDS. III. GENERATION OF STABLE IONS FROM LONGIFOLENE

The salts of the stable carbocations previously postulated for the rearrangement of longifolene (I) into isolongifolene (II) were generated, and their spectral characteristics and some of their chemical properties were studied.A scheme is proposed for the rearrangement of the compounds (I) -> (II).It was shown that if the optically active olefin (I) is used the degree of racemization of the product (II) decreases with decrease in the acidity of the medium as a result, evidently, of a change in the ratio of the rates of the intramolecular rearrangements in the initially formed cation (IV), depending on the nature of the medium.