41429-52-1

Basic information

• Product Name: (+)-Norpatchoulenol
• Synonyms: (+)-Norpatchoulenol;(1R)-1,2,4aβ,5,6,7,8,8a-Octahydro-8aβ,9,9-trimethyl-1α,6α-methanonaphthalene-1-ol;(1R)-4aβ,5,6,7,8,8a-Hexahydro-8aβ,9,9-trimethyl-1α,6α-methanonaphthalen-1β(2H)-ol;Norpatchoulenol
• CAS NO: 41429-52-1
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.3239
• Mol File: 41429-52-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 275.6°Cat760mmHg
• Flash Point: 114.3°C
• Appearance: /
• Density: 1.055g/cm³
• Vapor Pressure: 0.000631mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: (+)-Norpatchoulenol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Norpatchoulenol(41429-52-1)
• EPA Substance Registry System: (+)-Norpatchoulenol(41429-52-1)

Safety Data

• Hazardous Substances Data: 41429-52-1(Hazardous Substances Data)

Usage

Chemical Description

(+)-Norpatchoulenol is a natural product with a bicyclic structure, while (+)-camphor-10-sulphonic acid is a chiral starting material.

InChI:InChI=1/C14H22O/c1-12(2)10-6-8-13(3)11(9-10)5-4-7-14(12,13)15/h4-5,10-11,15H,6-9H2,1-3H3/t10-,11-,13+,14+/m0/s1

Upstream product

• 130852-87-8 (1S,4R,6R)-6-((S)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 130852-86-7 (1S,4R,6R)-6-((R)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 130740-90-8 (1S,4R)-6-[1-Methoxy-meth-(Z)-ylidene]-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 130852-84-5 (1S,2R,4R)-1,5,5-Trimethyl-6-oxo-bicyclo[2.2.2]octane-2-carbaldehyde 
• 77584-08-8 (1S,4R,6R)-6-((R)-1-Methoxymethoxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 62731-83-3 (1R,2R,4S)-1,5,5-Trimethyl-6-oxo-bicyclo[2.2.2]octane-2-carbaldehyde 
• 62731-83-3 1,5,5-trimethyl-6-oxobicyclo<2.2.2>octane-2-endo-2-carbaldehyde 
• 77584-07-7 (1R,4S,6S)-6-((S)-1-Hydroxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 57576-19-9 (1S,4R,4aR,6S,8aR)-1-Hydroxy-8a,9,9-trimethyl-decahydro-1,6-methano-naphthalene-4-carboxylic acid 
• 57576-18-8 (+/-)-hydroxy patchouli alcohol 
• 91997-91-0 (1S,4R,4aR,6S,8aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-8a,9,9-trimethyl-octahydro-1,6-methano-naphthalen-1-ol 
• 77646-42-5 (1R,4S,6S)-6-((S)-1-Hydroxy-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 

Relevant articles and documents

STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-NORPATCHOULENOL AND TWO METABOLITES OF PATCHOULI ALCOHOL, (+/-)-HYDROXY PATCHOULI ALCOHOL AND THE CORRESPONDING (+/-)-CARBOXYLIC ACID

The first total synthesis of the two biooxidation products of patchouli alcohol (2), (+/-)-hydroxy patchouli alcohol (3) and the corresponding (+/-)-carboxylic acid 4, has been achieved in highly stereocontrolled manners.Synthesis of (+/-)-norpatchoulenol (1), the real odoriferous substance of patchouli oil, has been accomplished by the biogenetic route via (+/-)-3 and (+/-)-4.

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A new total synthesis of (±) norpatchoulenol is described with a ScN′ type reaction as the key step.