4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl-
• CAS No.: 91682-96-1
• Molecular Formula: C₃₀H₄₂O₇
• Molecular Weight: 514.659
• European Community (EC) Number: 620-944-2
• DSSTox Substance ID: DTXSID40903940
• Wikipedia: Stigmatellin
• Mol file: 91682-96-1.mol

Synonyms:stigmatellin

Chemical Property of 4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl-

Chemical Property:

• Vapor Pressure: 1.01E-16mmHg at 25°C
• Melting Point: 129°C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 635°Cat760mmHg
• PKA: 8.67±0.40(Predicted)
• Flash Point: 198.1°C
• PSA: 87.36000
• Density: 1.081g/cm³
• LogP: 6.13760
• Storage Temp.: −20°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 514.29305367
• Heavy Atom Count: 37
• Complexity: 858

Purity/Quality:

98%Min ^*data from raw suppliers

STIGMATELLIN 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C=CC=CC(C(C)C(C(C)CCC1=C(C(=O)C2=C(O1)C(=C(C=C2OC)OC)O)C)OC)OC
• Isomeric SMILES: C/C=C(/C)\C=C\C=C\C(C(C)C(C(C)CCC1=C(C(=O)C2=C(O1)C(=C(C=C2OC)OC)O)C)OC)OC
• Uses: Stigmatellin is a cytochrome bc1 complex inhibitor.

Technology Process of 4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl-

There total 50 articles about 4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl- 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: 85.0%

allyl {2-[(3S,4S,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-5,7-dimethoxy-3-methyl-4-oxo-4H-chromen-8-yl} carbonate → stigmatellin A (91682-96-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; triphenylphosphine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1246/bcsj.20140271

Reference yield: 77.0%

(2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester (104701-95-3) + (2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal (276690-23-4) → stigmatellin A (91682-96-1)

Guidance literature:

(2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 15h;

(2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal; In tetrahydrofuran; hexane; at -78 - 20 ℃;

Reference yield:

1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)propan-1-one (94190-89-3) → stigmatellin A (91682-96-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / DIPEA / CH₂Cl₂ / 20 °C

2.1: 240 mg / DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: 75 percent / NaOMe / methanol / 2 h / Heating

4.1: 74 percent / H₂ / 10 percent Pd/C / methanol / 0.07 h

5.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

6.1: aq. HCl / CH₂Cl₂ / 0.5 h

7.1: LDA / tetrahydrofuran; hexane / 15 h / -78 °C

7.2: 77 percent / tetrahydrofuran; hexane / -78 - 20 °C

With hydrogenchloride; dmap; oxalyl dichloride; hydrogen; sodium methylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Etherification / 2.1: Esterification / 3.1: Cyclization / 4.1: Hydrogenolysis / 5.1: Swern oxidation / 6.1: Hydrolysis / 7.1: Metallation / 7.2: Condensation;

upstream raw materials:

(2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester

(2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal

(2S,3S,4S)-6-(8-Benzyloxy-5,7-dimethoxy-3-methyl-4-oxo-4H-chromen-2-yl)-3-methoxy-2,4-dimethyl-hexanal

methyl iodide

Downstream raw materials:

2,4-Dimethoxy-3,5-dimethyl-1,8-octandisaeure-bis(p-bromphenacylester)

Refernces

• 1、 Enders, Dieter,Geibel, Gunter,Osborne, Simon. "Diastereo- and enantioselective total synthesis of stigmatellin A". . p. 1302 - 1309. Retrieved 2007/10/03.