2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)-

Base Information

• Chemical Name: 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)-
• CAS No.: 81800-41-1
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• Hs Code.: 2932209090
• Mol file: 81800-41-1.mol

Synonyms:2(4H)-benzofuranone,5,6,7,7a-tetrahydro-4,4,7a-trimethyl;(S)-4,4,7a-Trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one;2(4H)-Benzofuranone,5,6,7,7a-tetrahydro-4,4,7a-trimethyl-,(S);4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one;(+/-)-dihydroactinidiolide;5,6,7,7a-tetrahydro-4,4,7a-trimethyl-2-(4H)-benzofuranone;

Chemical Property of 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)-

Chemical Property:

• Vapor Pressure: 0.00147mmHg at 25°C
• Melting Point: 36 °C
• Boiling Point: 296.1°C at 760 mmHg
• Flash Point: 120.2°C
• PSA: 26.30000
• Density: 1.05g/cm³
• LogP: 2.43840

Purity/Quality:

97% ^*data from raw suppliers

(S)-4,4,7A-Trimethyl-5,6,7,7A-tetrahydrobenzofuran-2(4H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Flavor ingredient; inhibitor of seed germination.

Technology Process of 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)-

There total 55 articles about 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)- 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: 92.0%

(2,6,6-trimethylcyclohex-1-enyl)acetic acid (472-68-4) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With diphenyl diselenide; tetraethylammonium bromide; water; sodium carbonate; In acetonitrile; for 0.6h; Ambient temperature; electrolysis under a constant current 70 mA;

DOI:10.1021/ja00405a064

Reference yield: 90.0%

(3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran (104446-40-4) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; acetic acid; at 0 - 20 ℃; for 4.5h;

DOI:10.1016/j.tetlet.2009.07.067

Reference yield: 87.0%

2,2-Diethoxy-4,4,7a-trimethyl-4,5,6,7,7a-pentahydro-2H-benzofuran (120211-66-7) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; water; for 2h;

DOI:10.1016/S0040-4020(01)86013-0

upstream raw materials:

4,4,7a-trimethylhexahydro-1-benzofuran-2(3H)-one

(+/-)-aeginetolide

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

(2,6,6-trimethylcyclohex-1-enyl)acetic acid

Downstream raw materials:

C₁₁H₂₀O₂

Refernces

Cyclisation of Polyenic β-Keto Sulphoxides. A Novel Route to Optically Active Intermediates for Cyclic Terpenoid Synthesis

10.1039/c39910001173

The research focuses on the cyclisation of polyenic β-keto sulphoxides as a novel route to optically active intermediates for cyclic terpenoid synthesis. The purpose of this study was to explore the potential of using polyenic β-keto sulphoxides as precursors for the biogenetic-like cyclisation of polyenes, which could lead to the synthesis of optically pure cyclic terpenoids. The researchers successfully demonstrated that optically active polyenic β-keto sulphoxides 4 and 5, when mediated by SnCl4, undergo cyclisation to yield diastereoisomeric dihydropyran derivatives 6a,b and 10a,b, respectively. These derivatives could be further converted into (+)-dihydroactinidiolide 7 and (-)-norambreinolide 11. The study concluded that this method provides an efficient route to optically active intermediates for the synthesis of cyclic terpenoids, using chemicals such as SnCl4, geranyl bromide, farnesyl bromide, and RuO2-NaIO4 in the process.