(+/-)-cis-4'-acetylkhellactone

Base Information

• Chemical Name: (+/-)-cis-4'-acetylkhellactone
• CAS No.: 4955-21-9
• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.299
• Mol file: 4955-21-9.mol

Synonyms:

Chemical Property of (+/-)-cis-4'-acetylkhellactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-cis-4'-acetylkhellactone

There total 6 articles about (+/-)-cis-4'-acetylkhellactone 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:

seseline (523-59-1) → (+/-)-cis-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent Turnov_. / OsO₄, N-methylmorpholine-N-oxide dihydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 72 h / Ambient temperature

2: 65 percent Turnov_. / BF₃*Et₂O / tetrahydrofuran / 2.8 h / Ambient temperature

With osmium(VIII) oxide; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.3987/R-1987-05-1239

Reference yield:

seseline (523-59-1) → qianhucomarin B (152615-14-0) + (+/-)-cis-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone / 24 h / 20 °C

2: dimethyltin dichloride; potassium carbonate / tetrahydrofuran / 24 h / 0 °C

With osmium(VIII) oxide; water; dimethyltin dichloride; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; acetone;

Reference yield:

seseline (523-59-1) + acetic acid (64-19-7,77671-22-8) → (+/-)-trans-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2)

Guidance literature:

With water; iodine; silver(I) acetate; Yield given. Multistep reaction; 1.) 30 min, 2.) from 95 to 100 deg C, 2 5 h;

DOI:10.3987/R-1987-05-1239

upstream raw materials:

seseline

acetic acid

acetyl chloride

(±)-cis-khellactone

Downstream raw materials:

(±)-cis-khellactone

(±)-trans-khellactone

(+/-)-trans-4'-acetyl-3'-isovalerylkhellactone

(+/-)-trans-4'-acetyl=3'-tigloylkhellactone

Refernces

• 1、 Bal-Tembe, Swati,Bhedi, Dilip N.,Souza, Noel J. de,Rupp, Richard Helmut. "SYNTHESIS OF (+/-)-PRAERUPTORIN A AND RELATED KHELLACTONE DERIVATIVES". . p. 1239 - 1249. Retrieved 2007/10/02.