Boschnialactone

Base Information

• Chemical Name: Boschnialactone
• CAS No.: 17957-87-8
• Deprecated CAS: 25368-14-3
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.209
• DSSTox Substance ID: DTXSID00939240
• Nikkaji Number: J37.623J
• Wikidata: Q27105962
• Metabolomics Workbench ID: 69307
• Mol file: 17957-87-8.mol

Synonyms:Boschnialactone;(-)-Boschnialactone;17957-87-8;C09772;(4aR,7R,7aR)-7-methyl-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one;AC1L9CSB;7-Methylhexahydrocyclopenta[c]pyran-3(1H)-one;CHEBI:3158;(6R)-9-METHYL-3-OXABICYCLO[4.3.0]NONAN-4-ONE;DTXSID00939240;Q27105962

Chemical Property of Boschnialactone

Chemical Property:

• Vapor Pressure: 0.00926mmHg at 25°C
• Boiling Point: 265.2°Cat760mmHg
• Flash Point: 105.1°C
• PSA: 26.30000
• Density: 1.04g/cm³
• LogP: 1.59560
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 176

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C1COC(=O)C2
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@@H]1COC(=O)C2

Technology Process of Boschnialactone

There total 123 articles about Boschnialactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(+/-)-cis-5,6,7,7a-tetrahydro-7-methylcyclopentapyran-3(1H)-one → (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one (16802-11-2,16802-12-3,16802-13-4,16802-14-5,17957-87-8,105181-38-2,131726-13-1)

Guidance literature:

With hydrogen; platinum; In ethanol; for 1h; under 760 Torr; Ambient temperature;

DOI:10.1248/cpb.43.26

Reference yield: 98.0%

(7R,7aR)-7-Methyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one (158512-67-5) → (-)-boschnialactone (17957-87-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h;

DOI:10.1016/S0040-4039(00)73091-7

Reference yield: 95.0%

7-(4-methylphenylsulfonyloxymethyl)-3-oxoperhydrocyclopenta[c]pyran → (+/-)-boschnialactone (16802-11-2,16802-12-3,16802-13-4,16802-14-5,17957-87-8,105181-38-2,131726-13-1)

Guidance literature:

With sodium iodide; zinc; In 1,4-dioxane; at 100 ℃; for 3h;

DOI:10.1002/jccs.199900032

upstream raw materials:

-2 ethanoate de tert-butyle

(4aS,7R,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

7-methoxy-heptane-2,5-dione

2-(methoxymethyl)-3-methyl-2-cyclopenten-1-one

Downstream raw materials:

(+/-)-Isoiridomyrmecin

(+/-)-iridomyrmecin

isoiridomyrmecin, iridomyrmecin

(+/-)-teucriumlactone C

Refernces

• 1、 Basante-Avenda?o, Alberto,Guerra-Ayala, Víctor E.,Sánchez-Eleuterio, Alma,Cordero-Vargas, Alejandro. "A Free-Radical and Protecting-Group-Free Approach to (-)-Boschnialactone and γ-Lycorane". . p. 2207 - 2213. Retrieved 2019.
• 2、 Salam, Abdus,Ray, Sayan,Zaid, Md. Abu,Kumar, Dileep,Khan, Tabrez. "Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic solution". . p. 6831 - 6842. Retrieved 2019/07/22.