2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(8-tridecenyl)-, (Z)-

Base Information

• Chemical Name: 2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(8-tridecenyl)-, (Z)-
• CAS No.: 97987-90-1
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Hs Code.: 2914690090
• Mol file: 97987-90-1.mol

Synonyms:5-hydroxy-2-methoxy-6-((Z)-8'-tridecenyl)-1,4-benzoquinone;ardisianone B

Chemical Property of 2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(8-tridecenyl)-, (Z)-

Chemical Property:

• Vapor Pressure: 1.66E-10mmHg at 25°C
• Boiling Point: 462.7°Cat760mmHg
• Flash Point: 154.6°C
• PSA: 63.60000
• Density: 1.068g/cm³
• LogP: 4.46440
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 514

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CCC(C=CCC)OC)C1=C(C(=O)C=CC1=O)O
• Isomeric SMILES: CCCCCC(CCC(/C=C/CC)OC)C1=C(C(=O)C=CC1=O)O

Technology Process of 2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(8-tridecenyl)-, (Z)-

There total 11 articles about 2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(8-tridecenyl)-, (Z)- 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: 53.0%

(Z)-1-(2,3,5,6-tetramethoxyphenyl)-8-tridecene (219144-62-4) → 2-hydroxy-5-methoxy-3-(Z-8-tridecenyl)-1,4-benzoquinone (97987-90-1) + 2,5-dimethoxy-3-(Z-8-tridecenyl)-1,4-benzoquinone (99621-95-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; 1.) -7 deg C, 1 h, 2.) room temp., 2 h;

DOI:10.1016/S0040-4020(98)00927-2

Reference yield:

1,7-dibromoheptane (4549-31-9) → 2-hydroxy-5-methoxy-3-(Z-8-tridecenyl)-1,4-benzoquinone (97987-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1: HMPA, Ph₃CH, n-BuLi / tetrahydrofuran / 48 h / Heating

2: H₂ / Pd/CaCO₃/Pb / benzene / 12 h / 760 Torr

3: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight

4: 1.) ammonium cerium(IV) nitrate, 2.) HClO₄ / 1.) CH₃CN, H₂O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH₂Cl₂, room temp., 4 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; perchloric acid; ammonium cerium(IV) nitrate; triphenylmethane; hydrogen; Lindlar's catalyst; In tetrahydrofuran; benzene;

DOI:10.1016/S0040-4020(98)00927-2

Reference yield:

1-bromo-8-tridecyne (80436-75-5) → 2-hydroxy-5-methoxy-3-(Z-8-tridecenyl)-1,4-benzoquinone (97987-90-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/CaCO₃/Pb / benzene / 12 h / 760 Torr

2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight

3: 1.) ammonium cerium(IV) nitrate, 2.) HClO₄ / 1.) CH₃CN, H₂O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH₂Cl₂, room temp., 4 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; perchloric acid; ammonium cerium(IV) nitrate; hydrogen; Lindlar's catalyst; In benzene;

DOI:10.1016/S0040-4020(98)00927-2

upstream raw materials:

(Z)-1-(2,3,5,6-tetramethoxyphenyl)-8-tridecene

1,7-dibromoheptane

1,2,4,5-tetramethoxybenzene

asaraldehyde

Downstream raw materials:

1-(2,5-dimethoxy-1,4-benzoquinon-3-yl)-8,9-epoxytridecane

2,5-dimethoxy-3-(Z-8-tridecenyl)-1,4-benzoquinone