2,5-Cyclohexadiene-1,4-dione,3-[(8Z)-16-(3,- 5-dihydroxy-4-methylphenyl)-8- hexadecenyl]-2-hydroxy-5-methoxy-

Base Information

• Chemical Name: 2,5-Cyclohexadiene-1,4-dione,3-[(8Z)-16-(3,- 5-dihydroxy-4-methylphenyl)-8- hexadecenyl]-2-hydroxy-5-methoxy-
• CAS No.: 99621-86-0
• Molecular Formula: C₃₀H₄₂O₆
• Molecular Weight: 498.66
• Mol file: 99621-86-0.mol

Synonyms:

Chemical Property of 2,5-Cyclohexadiene-1,4-dione,3-[(8Z)-16-(3,- 5-dihydroxy-4-methylphenyl)-8- hexadecenyl]-2-hydroxy-5-methoxy-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-Cyclohexadiene-1,4-dione,3-[(8Z)-16-(3,- 5-dihydroxy-4-methylphenyl)-8- hexadecenyl]-2-hydroxy-5-methoxy-

There total 19 articles about 2,5-Cyclohexadiene-1,4-dione,3-[(8Z)-16-(3,- 5-dihydroxy-4-methylphenyl)-8- hexadecenyl]-2-hydroxy-5-methoxy- 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: 80.0%

1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene (219630-97-4) → ardisiaquinone F (99621-86-0)

Guidance literature:

With perchloric acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.1770

Reference yield:

1,7-dibromoheptane (4549-31-9) → ardisiaquinone F (99621-86-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, hexane, -78 deg C, 1 h, 2.) toluene, hexane, from -78 deg C to RT, 2.5 h

2: 1.) nBuLi, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, 4.5 h

3: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight

5: H₂ / Pd/BaSO₄ / pyridine / 36 h

6: 1.) 48 percent aq. HBr, 2.) O₂, NaHCO₃ / 1.) MeOH, 50 deg C, 15 min, 2.) MeOH, 30 min

7: 80 percent / 70 percent aq. HClO₄ / CH₂Cl₂ / 1 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; perchloric acid; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; oxygen; sodium hydrogencarbonate; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1248/cpb.46.1770

Reference yield:

1,3-dimethoxy-5-(7'-hydroxyheptyl)benzene (52483-31-5) → ardisiaquinone F (99621-86-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / Amberlist-15 / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) n-BuLi, TMEDA / 1.) hexane, -20 deg C, 1 h, 2.) hexane, THF, RT, 4 h

3: 67 percent / p-toluenesulfonic acid, MeOH / 24 h

4: 1.3 g / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 94 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

6: 86 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / Ambient temperature

7: 95 percent / NaI / acetone / 48 h / Heating

8: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight

9: H₂ / Pd/BaSO₄ / pyridine / 36 h

10: 1.) 48 percent aq. HBr, 2.) O₂, NaHCO₃ / 1.) MeOH, 50 deg C, 15 min, 2.) MeOH, 30 min

11: 80 percent / 70 percent aq. HClO₄ / CH₂Cl₂ / 1 h / Ambient temperature

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; perchloric acid; N,N,N,N,-tetramethylethylenediamine; Amberlist-15; hydrogen bromide; hydrogen; oxygen; boron tribromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium diisopropyl amide; Pd-BaSO₄; In pyridine; dichloromethane; acetone;

DOI:10.1248/cpb.46.1770

upstream raw materials:

1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene

1,7-dibromoheptane

1,3-dimethoxy-5-(7'-hydroxyheptyl)benzene

6-benzyloxy-1-hexanal