triptonolide

Base Information

• Chemical Name: triptonolide
• CAS No.: 79548-61-1
• Molecular Formula: C20H22 O4
• Molecular Weight: 326.392
• Mol file: 79548-61-1.mol

Synonyms:Phenanthro[1,2-c]furan-1,5-dione,3,3b,4,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-, (3bR-trans)-;Triptonolide

Chemical Property of triptonolide

Chemical Property:

• Vapor Pressure: 5.91E-13mmHg at 25°C
• Boiling Point: 555.7°C at 760 mmHg
• Flash Point: 201.6°C
• PSA: 63.60000
• Density: 1.28g/cm³
• LogP: 3.62310

Purity/Quality:

99% ^*data from raw suppliers

(3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[2,1-c]furan-1,5(3H,9bH)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of triptonolide

There total 42 articles about triptonolide 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%

(3bR,9bS)-7-Isopropyl-6-methoxy-9b-methyl-3,3b,4,9b,10,11-hexahydro-phenanthro[1,2-c]furan-1,5-dione (225786-93-6) → (3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione (79548-61-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 2h;

DOI:10.1021/jo9919613

Reference yield: 79.0%

(3bR,9bS)-6-hydroxy-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione (1209485-42-6) + isopropyl alcohol (67-63-0,8013-70-5) → (3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione (79548-61-1)

Guidance literature:

With trifluorormethanesulfonic acid; at 0 - 65 ℃; for 3h; Reagent/catalyst; Inert atmosphere;

Reference yield: 71.0%

(S)-6-hydroxy-7-isopropyl-9b-methyl-10,11-dihydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione (1408320-09-1) → (3bR,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione (79548-61-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 2h; Reagent/catalyst;

upstream raw materials:

(3bR,9bS)-7-Isopropyl-6-methoxy-9b-methyl-3,3b,4,9b,10,11-hexahydro-phenanthro[1,2-c]furan-1,5-dione

(S)-6-hydroxy-7-isopropyl-9b-methyl-10,11-dihydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione

(4aS,10aS)-ethyl 8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate

(4aS,10aR)-ethyl 8-methoxy-4a-methyl-2-(((trifluoromethyl)sulfonyl)oxy)-3,4,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate

Downstream raw materials:

l-triptonide

triptolide

Refernces

• 1、 -. "The triptolide method for the asymmetric synthesis of intermediates". . . Retrieved 2019/02/02.
• 2、 Zhang, Hongrui,Li, Haifeng,Xue, Jijun,Chen, Rui,Li, Ying,Tang, Yu,Li, Chunxin. "New facile enantio- and diastereo-selective syntheses of (-)-triptonide and (-)-triptolide". supporting information. p. 732 - 736. Retrieved 2014/01/23.