Chaetomellic Acid B Anhydride

Base Information

• Chemical Name: Chaetomellic Acid B Anhydride
• CAS No.: 84306-79-6
• Molecular Formula: C21H34O3
• Molecular Weight: 334.499
• DSSTox Substance ID: DTXSID20438028
• Nikkaji Number: J875.190K,J741.549D
• Wikidata: Q82253638
• Metabolomics Workbench ID: 143810
• Mol file: 84306-79-6.mol

Synonyms:Chaetomellic Acid B Anhydride;Chaetomellic Anhydride B;84306-79-6;3-[(Z)-hexadec-7-enyl]-4-methylfuran-2,5-dione;SCHEMBL9188758;DTXSID20438028;3-[(Z)-7-Hexadecenyl]-4-methyl-2,5-furandione

Chemical Property of Chaetomellic Acid B Anhydride

Chemical Property:

• PSA: 43.37000
• LogP: 6.03370
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

98% ^*data from raw suppliers

Chaetomellic Acid B Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCC1=C(C(=O)OC1=O)C
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCC1=C(C(=O)OC1=O)C

Technology Process of Chaetomellic Acid B Anhydride

There total 18 articles about Chaetomellic Acid B Anhydride 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:

3-Hexadec-7-ynyl-4-methyl-furan-2,5-dione (177099-98-8) → 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione (84306-79-6)

Guidance literature:

With hydrogen; Lindlar catalyst; In cyclohexane; for 40h; under 760 Torr; Yield given; Ambient temperature;

DOI:10.1021/jo9601977

Reference yield:

1 ,6-dibromohexane (629-03-8) → 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione (84306-79-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / Ph₃CH, HMPA, BuLi / tetrahydrofuran / 44 h / Heating

2: 1.) NaH / 1.) THF, DMF, room temperature, 15 min, 2.) reflux, 1.5 h

3: 1.) NaH / 1.) THF, DMF, room temperature, 15 min, 2.) reflux, 1.5 h

4: 1.) KOH, 2.) conc. HCl / 1.) EtOH, reflux, 8-10 h, 2.) pH 2, reflux, 18 h

5: N-methylmorpholine, methyl chloroformate / tetrahydrofuran / 0.25 h / Ambient temperature

6: Et₃N / benzene / 2 h / Heating

7: n-Bu₄NBr, NBS / benzene; CH₂Cl₂ / 0.25 h / 0 °C

8: H₂ / Pd/CaCO₃/PbO / cyclohexane / 40 h / 760 Torr / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; triphenylmethane; tetrabutylammomium bromide; hydrogen; sodium hydride; triethylamine; methyl chloroformate; Lindlar catalyst; In tetrahydrofuran; dichloromethane; cyclohexane; benzene;

DOI:10.1021/jo9601977

Reference yield:

1-decyne (764-93-2) → 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione (84306-79-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / Ph₃CH, HMPA, BuLi / tetrahydrofuran / 44 h / Heating

2: 1.) NaH / 1.) THF, DMF, room temperature, 15 min, 2.) reflux, 1.5 h

3: 1.) NaH / 1.) THF, DMF, room temperature, 15 min, 2.) reflux, 1.5 h

4: 1.) KOH, 2.) conc. HCl / 1.) EtOH, reflux, 8-10 h, 2.) pH 2, reflux, 18 h

5: N-methylmorpholine, methyl chloroformate / tetrahydrofuran / 0.25 h / Ambient temperature

6: Et₃N / benzene / 2 h / Heating

7: n-Bu₄NBr, NBS / benzene; CH₂Cl₂ / 0.25 h / 0 °C

8: H₂ / Pd/CaCO₃/PbO / cyclohexane / 40 h / 760 Torr / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; triphenylmethane; tetrabutylammomium bromide; hydrogen; sodium hydride; triethylamine; methyl chloroformate; Lindlar catalyst; In tetrahydrofuran; dichloromethane; cyclohexane; benzene;

DOI:10.1021/jo9601977

upstream raw materials:

3-Hexadec-7-ynyl-4-methyl-furan-2,5-dione

citraconic acid anhydride

(Z)-Heptadec-8-enoic acid 2-thioxo-2H-pyridin-1-yl ester

(Z)-1-bromoheptadec-8-ene

Downstream raw materials:

nonanoic acid methyl ester

Refernces

• 1、 Kates, Michael J.,Herman Schauble. "Total synthesis of chaetomellic anhydrides A and B via a novel succinate to maleate oxidation". . p. 4164 - 4167. Retrieved 2007/10/03.