2630-39-9

Basic information

• Product Name: methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate
• Synonyms: methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1R,2R)-;(-)-trans-Dihydrojasmonic acid methyl;(1R)-2β-Amyl-3-oxo-1-cyclopentaneacetic acid methyl ester;(1R)-2β-Pentyl-3-oxocyclopentane-1α-acetic acid methyl ester;(1R)-3-Oxo-2β-pentylcyclopentane-1α-acetic acid methyl ester;2-(2-amyl-3-keto-cyclopentyl)acetic acid methyl ester;methyl 2-(3-oxo-2-pentylcyclopentyl)acetate
• CAS NO: 2630-39-9
• Molecular Formula: C13H22O3
• Molecular Weight: 226.31198
• EINECS: 220-112-5
• Mol File: 2630-39-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: bp0.03 100°
• Flash Point: 130.816 °C
• Appearance: /
• Density: d421 0.9968
• Vapor Pressure: 0.00071mmHg at 25°C
• Refractive Index: nD20 1.4583
• CAS DataBase Reference: methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate(2630-39-9)
• EPA Substance Registry System: methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate(2630-39-9)

Safety Data

• Hazardous Substances Data: 2630-39-9(Hazardous Substances Data)

Usage

General Description

Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate, also referred to as Ambroxide or C16H26O3, is a chemical compound typically used in fragrance creation due to its exceptional fixative properties. It has a complex, pleasant aroma classified as ambergris, woody, amber, warm, and sweet, which is why it is popular in perfumery. This chemical is also noted for its high stability, non-toxicity, and ability to improve and extend a scent's longevity. It's important to note that though it can be naturally sourced from ambergris, most of the Ambroxide used today is synthetically produced due to sustainability and cost-efficiency reasons.

InChI:InChI=1/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3/t10-,11-/m1/s1

Upstream product

• 24863-70-5 (3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester 
• 51806-24-7 methyl 1-hydroxy-2-pentylcyclopent-2-eneacetate 
• 154828-89-4 2-pentyl-2,3-epoxy-1-cyclopentanone 
• 119009-18-6 methyl (1R,2R,3S)-3-hydroxy-2-pentylcyclopentaneacetate 
• 186581-53-3 diazomethane 
• 3572-64-3 2-(3-oxy-2-pentylcyclopentyl)acetic acid 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 
• 67-56-1 methanol 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 67-63-0 isopropyl alcohol 
• 54562-27-5 ((1R,2S,3R)-3-Hydroxy-2-pentyl-cyclopentyl)-acetic acid methyl ester 
• 128893-61-8 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester 
• 122248-64-0 (+)-methyl 2-((1S,5R)-4-oxo-5-pentylcyclopent-2-en-1-yl)acetate 
• 145356-31-6 4,5-didehydro-9,10-dihydrojasmonic acid 

Downstream Products

• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 1128-08-1 dihydro-cis-jasmone 
• 96844-45-0 (+)-9,10-dihydro-7-iso-jasmonic acid 

Relevant articles and documents

Further explorations into the synthesis of Dehydro-Hedione

Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b, followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3-chloroperbenzoic acid, CH2Cl2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1: 2 mixture of 8a and 8b. The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (tBuO2H, [Mo(CO)6], 1,2-dichloroethane, 70°, 62% yield; or tBuO2H, [VO(acac)2], decane, 20°, 92% yield), or from 5 (AcOMe, LiN(SiMe3)2, THF, -78°, 84-87%). BF3×Et2O-Catalyzed cascade rearrangement and OH elimination of 8a afford selectively DHH 1 in 88% yield. The cis disposition of the side chains of the weakly odoriferous hedione-like analogues 2b and 2c was maintained by means of either an epoxy or a cyclopropane moiety. Copyright

Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation

The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.

A new variant of the Claisen rearrangement from malonate-derived allylic trimethylsilyl ketene acetals: Efficient, highly enantio- and diastereoselective syntheses of (+)-methyl dihydroepijasmonate and (+)-methyl epijasmonate

Complete chirality transfer occurs in the smooth Claisen rearrangement of the trimethylsilyl (TMS) ketene acetals, which were prepared from allylic malonates (R)-1 (R = pentyl, 2-(Z)-pentenyl). These are in turn accessible by enantioselective reduction/esterification or by enzymatic kinetic resolution. The cis configuration in (+)-3 was achieved by highly syn-selective epoxidation of (+)-2, followed by suprafacial 1,2-H migration.