511-59-1

Basic information

• Product Name: (1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane
• Synonyms: (1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane;2-methyl-3-methylene-2-(4-methylpent-3-enyl)norbornane;6-methyl-5-methylidene-6-(4-methylpent-3-enyl)bicyclo[2.2.1]heptane;(-)-beta-santalene
• CAS NO: 511-59-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• EINECS: 208-130-1
• Mol File: 511-59-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 260.1 °C at 760 mmHg
• Flash Point: 100.8 °C
• Appearance: /
• Density: 0.89 g/cm³
• Vapor Pressure: 0.0202mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: (1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane(511-59-1)
• EPA Substance Registry System: (1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane(511-59-1)

Safety Data

• Hazardous Substances Data: 511-59-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A sesquiterpene and carbobicyclic compound that is bicyclo[2.2.1]heptane in which the hydrogens at position 3 are substituted by a methylidene group, while the 2-exo- and 2-endo- hydrogens are subsitituted by 2-methylpent- -en-5-yl and methyl groups, respectively (the 1S,2R,4R enantiomer).

InChI:InChI=1/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3

Upstream product

• 512-61-8 (+)-α-santalene 
• 77-42-9 (-)-(Z)-β-santalol 
• 131232-80-9 3-(2-Methyl-3-methylenebicyclo<2.2.1>hept-2-yl)propanal 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 131726-03-9 (1R,3R,4S)-3-Methyl-3-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptan-2-one 
• 74-95-3 1,1-dibromomethane 
• 43161-11-1 5-iodo-2-methylpent-2-ene 
• 18530-03-5 (+/-)-Isoepicampherenol 
• 88941-07-5 (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1S,2S)-3-methylidene-2-(4-methyl-3-pentenyl)bicyclo<2.2.1>heptane-2-carboxylate 
• 131232-79-6 3-(2-Methyl-3-methylenebicyclo<2.2.1>hept-2-yl)propanenitrile 
• 67-56-1 methanol 
• 37172-32-0 (2E)-2-methyl-5-(2-methyl-3-methylidenebicyclo[2.2.1]hept-2-yl)pent-2-en-1-ol 
• 7664-41-7 ammonia 
• 106708-91-2 (1S,2S)-3-methylidene-2-(4-methyl-3-pentenyl)bicyclo<2.2.1>heptane-2-methanol 

Downstream Products

• 77-42-9 (-)-(Z)-β-santalol 

Relevant articles and documents

A SESQUITERPENOID ANT REPELLENT FROM DYSOXYLUM SPECTABILE

(2S,3R)-2,3-Dimethyl-3-(4-methyl-3-pentenyl)-2-norbornanol was isolated as the ant repellent in an activity guided separation of the fruits of Dysoxylum spectabile.The structure of the alcohol was established by NMR.Other sesquiterpenes were recognized in a GCMS analysis of the steam distillate.

Syntheses of epi-β-santalene, β-santalene and an isomer of β-santalene with 4-methyl-4-pentenyl side chain

-

Total Syntheses of Sandalwood Fragrances: (Z)- and (E)-β-Santalol and Their Enantiomers, ent-β-Santalene

Via asymmetric Diels-Alder reactions, large scale preparations of enantiomerically pure norbornane-2-carboxylic acids were carried out.Oxidative degradation furnished 2-norbornanone and 3-methyl-2-norbornanone which gave the title compounds via stereoselective alkylations, subsequent Wittig reactions and reductions.