Khellactone, trans-(+)-

Base Information

• Chemical Name: Khellactone, trans-(+)-
• CAS No.: 20516-17-0
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• UNII: T15EPI22YM
• ChEMBL ID: CHEMBL1452260
• Nikkaji Number: J2.739.453A
• Wikidata: Q105030012
• Mol file: 20516-17-0.mol

Synonyms:(+)-trans-khellactone;Khellactone, trans-(+)-;trans-(+)-Khellactone;T15EPI22YM;UNII-T15EPI22YM;20516-17-0;(9S,10R)-9,10-Dihydro-9,10-dihydroxy-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-2-one;2H,8H-Benzo(1,2-b:3,4-b')dipyran-2-one, 9,10-dihydro-9,10-dihydroxy-8,8-dimethyl-, (9S,10R)-;2H,8H-Benzo(1,2-b:3,4-b')dipyran-2-one, 9,10-dihydro-9,10-dihydroxy-8,8-dimethyl-, (9S-trans)-;MLS002472925;CHEMBL1452260;HMS2198O12;SMR001397036

Chemical Property of Khellactone, trans-(+)-

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 262.08412354
• Heavy Atom Count: 19
• Complexity: 416

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C(C2=C(O1)C=CC3=C2OC(=O)C=C3)O)O)C
• Isomeric SMILES: CC1([C@H]([C@@H](C2=C(O1)C=CC3=C2OC(=O)C=C3)O)O)C

Technology Process of Khellactone, trans-(+)-

There total 98 articles about Khellactone, trans-(+)- 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: 98.0%

seseline (523-59-1) → (±)-cis-khellactone (518-76-3,4968-31-4,15575-68-5,15645-11-1,20516-17-0,23458-04-0,24144-61-4,54712-23-1,80124-45-4)

Guidance literature:

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 24h;

Reference yield: 95.0%

(+)-(3'S,4'S)-seselin epoxide (1148112-58-6) → (+)-(3'S,4'R)-trans-khellactone (518-76-3,4968-31-4,15575-68-5,15645-11-1,23458-04-0,24144-61-4,54712-23-1,80124-45-4,20516-17-0)

Guidance literature:

With sulfuric acid; In water; acetone; at 20 ℃; for 1h; optical yield given as %ee;

DOI:10.1021/ol900444h

Reference yield: 74.0%

(+)-(3'R,4'R)-3'-acetyl-4'-angeloylkhellactone (20098-03-7,27800-79-9,130464-56-1,130464-57-2,13161-75-6) → Angelic acid (565-63-9) + (+)-cis-khellactone (518-76-3,4968-31-4,15575-68-5,15645-11-1,20516-17-0,23458-04-0,24144-61-4,54712-23-1,80124-45-4) + trans-kellactone (518-76-3,4968-31-4,15575-68-5,15645-11-1,20516-17-0,23458-04-0,24144-61-4,54712-23-1,80124-45-4)

Guidance literature:

(+)-(3'R,4'R)-3'-acetyl-4'-angeloylkhellactone; With potassium hydroxide; water; at 60 ℃; for 2h;

With sulfuric acid; water; pH=4;

DOI:10.1007/s10600-008-9144-6

upstream raw materials:

(+)-samidin

hystrixarin

junosmarin

campestrinol

Downstream raw materials:

trans-4'-O-methylkhellactone

(+/-)-3',4'-ditigloylkhellactone

cis-3'-senecioylkhellactone

3,4-disenecioyloxy-3,4-dihydroseselin