131726-13-1

Basic information

• Product Name: (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one
• CAS NO: 131726-13-1
• Molecular Weight: 154.209
• Mol File: 131726-13-1.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one(131726-13-1)
• EPA Substance Registry System: (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one(131726-13-1)

Safety Data

• Hazardous Substances Data: 131726-13-1(Hazardous Substances Data)

Upstream product

• 100475-84-1 -2 ethanoate de tert-butyle 
• 89502-68-1 (4aS,7R,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 
• 100475-83-0 Methoxymethyl-2 methyl-1 -3 cyclopentene-1 
• 89502-68-1 (4aS,7S,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 
• 4166-63-6 1-methylbicyclo[2.2.2]oct-5-ene-2-one 
• 28839-89-6 (1S,2S,3S,6S,7R,9S)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 89502-66-9 (1R,4R,5S,6R)-5-Hydroxymethyl-6-methyl-bicyclo[2.2.1]heptan-2-one 
• 89502-74-9 (1R,3R,6R,7S,9R)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-one 

Downstream Products

• 485-43-8 iridomyrmecin 
• 485-43-8 isoiridomyrmecin 
• 485-43-8 isoiridomyrmecin, iridomyrmecin 
• 485-43-8 (+/-)-Isoiridomyrmecin 
• 485-43-8 (+/-)-iridomyrmecin 
• 60419-55-8 (+/-)-teucriumlactone C 
• 60419-55-8 (+)-teucriumlactone 

Relevant articles and documents

Cyclopentenyllithium Additions to Chiral Aldehydes. Diastereofacial Selectivity Indicating the Absence of a Pronounced Neighboring Carboxylate Anion Effect

The 1,2-addition of cyclopentenyllithium to a series of three five-membered aldehydo esters and their hemiacylals has been examined in order to assess the level and direction of facial selectivity surrounding nucleophilic attack at the aldehyde carbonyl and to clarify possible electronic and steric contributions stemming from neighboring functional groups.Neither methyl substitution of the acetic acid (ester) side chain nor the interchange of ester for carboxylate anion serve as important diastereocontrol elements.Instead, diastereofacial selectivity in these and related cyclic carboxyaldehydes is governed by the inherent structural features of the ring system to which the functional group is attached.The convinient preparation of a complete subset of isomerically pure bicyclic lactones carrying five stereogenic centers is reported.

Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic solution

A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson-Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3-5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A.

Formal synthesis of (±)-hop ether, (±)-isoboonein, and (±)-iridomyrmecin

A general synthesis of (±)-hop ether (5), (±)-isoboonein (6), and (±)-iridomyrmecin (7) from bicyclo[2.2.1]ketone (9) is described. Cyclopentenoid aldehyde (10) and bicyclo[3.2.1]lactone (11) are the key intermediates.

A novel route to iridoids: Enantioselective syntheses of isoiridomyrmecin and α-skytanthine

Enantio- and diastereoselective syntheses of the iridoids (-)-isoiridomyrmecin and (+)-α-skytanthine from a common intermediate (6-bromo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one) were achieved. Key steps in both syntheses are conjugated nucleophilic substitutions (SN2′ anti-reactions) with C1 zinc cyanocu-prates.

Total synthesis of (±)-boschnialactone and (±)-tetrahydroanhydrodesoxyaucubigenin

A total synthesis of (±)-boschnialactone (1) and (±)-tertahydroanhydrodesoxyaucubigenin (2) is described and trisubstitued cyclopentenoid 3 is a key intermediate.

Total Synthesis of (±)-Patriscabrol and (±)-Boschnialactone

A total synthesis of (±)-patriscabrol (1) and (±)-boschnialactone (2) is described. The cyclopentapyranone skeleton is assembled by means of Baeyer-Villiger oxidation of ketol 5.

Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester

Formal syntheses of (±)-boschnialactone (5) and three cyclopentano-monoterpene lactones [i.e., (±)-(iridomyrmecin (6), (±)-isoiridomyrmecin (7), and (±)-allodolicholactone (8)] have been accomplished in the form of the syntheses of 2-(methoxymethyl)-3-methyl-2-cyclopenten-1-one (11) and (±)-(4aα,7α,7aα)-hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one (19), respectively, starting from 6,7-dihyd;ocyclopenta-1,3-dioxin-5(4H)-one (2). A synthesis of (±)-isodehydroiridomyrmecin (9) has also been achieved through a route including direct substitution of the hydroxy group of 2-(tert-butyldimethylsilyloxymethyl)-3- methyl-2-cyclopenten-1-ol (22) with 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (23) as a key step.

AN EXPEDIENT AND STEREOSELECTIVE SYNTHESIS OF (+/-) BOSCHNIALACTONE

An expedient and stereoselective synthesis of (+/-) boschnialactone via an easily accessible cyclopentenone is described, the three asymmetric centers being formed in a single hydrogenation step.

IRIDOIDS : STEREOSPECIFIC SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANOID INTERMEDIATES VIA BICYCLOHEPTANONES

An efficient synthesis of functionalized trialkyl substituted cyclopentanoids is presented.Stereocontrol is secured by their formation from norbornane precursors.The strategy is illustrated by the total synthesis of (+/-)-boschnialactone (13), (+/-)-teucriumlactone C (14), and (+/-)-loganin (2).