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(6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is a bicyclic chemical compound with a unique structure that features a six-membered ring and a three-membered oxygen-containing ring. It has a molecular formula of C9H14O2 and a molecular weight of 154.21 g/mol. As a ketone, it contains a carbonyl group, and the (6R) designation specifies the stereochemistry of the molecule. (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is known for its potential applications in various fields due to its distinct structure and reactivity.

17957-87-8

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17957-87-8 Usage

Uses

Used in Organic Synthesis:
(6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is used as an intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable building block for creating a wide range of molecules with different properties and applications.
Used as a Flavoring Agent:
In the food and beverage industry, (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is used as a flavoring agent. Its distinct chemical structure contributes to the development of specific flavors and scents, enhancing the overall sensory experience of various products.
Used in Medicinal Chemistry and Pharmaceutical Research:
(6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one holds potential in medicinal chemistry and pharmaceutical research. Its unique structure and reactivity make it a promising candidate for the development of new drugs and therapeutic agents. Researchers can leverage its properties to design and synthesize novel compounds with potential applications in treating various diseases and medical conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 17957-87-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,9,5 and 7 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 17957-87:
(7*1)+(6*7)+(5*9)+(4*5)+(3*7)+(2*8)+(1*7)=158
158 % 10 = 8
So 17957-87-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O2/c1-6-2-3-7-4-9(10)11-5-8(6)7/h6-8H,2-5H2,1H3/t6-,7-,8-/m1/s1

17957-87-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-boschnialactone

1.2 Other means of identification

Product number -
Other names (4aR,7R,7aR)-7-Methyl-hexahydro-cyclopenta[c]pyran-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17957-87-8 SDS

17957-87-8Relevant articles and documents

Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products

Chavez, David E.,Jacobsen, Eric N.

, p. 2563 - 2565 (2003)

(Matrix presented) Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.

A Free-Radical and Protecting-Group-Free Approach to (-)-Boschnialactone and γ-Lycorane

Basante-Avenda?o, Alberto,Guerra-Ayala, Víctor E.,Sánchez-Eleuterio, Alma,Cordero-Vargas, Alejandro

, p. 2207 - 2213 (2019)

The protecting-group-free (PGF) and free-radical-based synthesis of two structurally different natural products, (-)-boschnialactone and γ-lycorane, is reported. The key step in both syntheses is a radical-ionic sequence for construction of the principal structure (a six-membered lactone and a 1,4-dicarbonyl compound, respectively), allowing short and rapid access to these natural products through a PGF route.

Intramolecular Horner-Wadsworth-Emmons reaction in base sensitive substrates: Enantiospecific synthesis of iridoid monoterpene lactones

Nangia,Prasuna,Bheema Rao

, p. 3755 - 3758 (1994)

The cyclopentapyranones (-)-7 and (-)-13, representing the cis-fused 9- carbon core of iridoid lactones, are synthesised from (+)-pulegone.

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

Salam, Abdus,Ray, Sayan,Zaid, Md. Abu,Kumar, Dileep,Khan, Tabrez

, p. 6831 - 6842 (2019/07/22)

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

Chang, Meng-Yang,Hsu, Ru-Ting,Lin, Chun-Yu,Chen, Bor-Fong,Lin, Shiang-Tsern,Chang, Nein-Chen

, p. 271 - 282 (2007/10/03)

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

Ernst, Martin,Helmchen, Guenter

, p. 1953 - 1955 (2007/10/03)

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

Chang, Meng-Yang,Lin, Ching-Han,Lee, An-Yang,Tai, Huo-Mu,Chang, Nein-Chen

, p. 205 - 210 (2007/10/03)

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

Chiu, Jiun-Yuh,Chiu, Chih-Tsao,Chang, Nein-Chen

, p. 59 - 63 (2007/10/03)

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.

Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization

Taniguchi, Takahiko,Goto, Yasuo,Ogasawara, Kunio

, p. 707 - 709 (2007/10/03)

A cyclobutanone possessing a bicyclo[2.2.1]heptene framework {endo-tricyclo[4.2.1.02,5]non-7-en-3-one} has been prepared in both enantiomeric forms employing lipase-mediated kinetic resolution as the key step. To determine the absolute configuration, as well as to demonstrate the synthetic potential, both enantiomers of the cyclobutanone obtained have been transformed enantioconvergently into the key intermediate of the sesquiterpene (+)-β-santalene and the iridoid monoterpene (-)-boschnialactone.

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

Ohba,Haneishi,Fuji

, p. 26 - 31 (2007/10/02)

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.

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