4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methylpenta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

Base Information

• Chemical Name: 4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methylpenta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione
• CAS No.: 134985-00-5
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.429
• DSSTox Substance ID: DTXSID901043757
• Mol file: 134985-00-5.mol

Synonyms:furaquinocin E

Chemical Property of 4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methylpenta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

Chemical Property:

• Vapor Pressure: 8.6E-17mmHg at 25°C
• Boiling Point: 631°Cat760mmHg
• Flash Point: 221.8°C
• PSA: 93.06000
• Density: 1.3g/cm³
• LogP: 3.22500
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 384.15728848
• Heavy Atom Count: 28
• Complexity: 763

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C2=C(C=C3C(=C2O1)C(=O)C(=C(C3=O)OC)C)O)(C)C=CC=C(C)CO
• Isomeric SMILES: CC1C(C2=C(C=C3C(=C2O1)C(=O)C(=C(C3=O)OC)C)O)(C)/C=C/C=C(\C)/CO

Technology Process of 4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methylpenta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

There total 15 articles about 4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methylpenta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione 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: 65.0%

(2R,3R)-3-[(1E,3E)-(tert-butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-4-triisopropylsilanyloxy-2,3-dihydro-naphtho[1,2-b]furan-6,9-dione (474418-86-5) → furaquinocin E (134985-00-5)

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ja0364118

Reference yield: 41.0%

C36H32O8 (143893-05-4) → furaquinocin E (134985-00-5)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/S0040-4039(00)91714-3

Reference yield:

2-iodoresorcinol (41046-67-7) → furaquinocin E (134985-00-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Pd₂(dba)3*CHCl₃; (1R,2R)-bis[2-(di-Ph-phosphinyl)-benzamino]-1,2-di-Ph-ethane / CH₂Cl₂ / 4 h / 20 °C

2.1: PdCl₂(CH₃CN)2; 1,2,2,6,6-pentamethylpiperidine; formic acid / dimethylformamide / 6 h / 50 °C

3.1: 96 percent / TEA / CH₂Cl₂

4.1: 92 percent / NBS / tetrahydrofuran / 20 °C

5.1: DIBAL-H / CH₂Cl₂ / -78 °C

6.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C

6.2: 368 mg / tetrahydrofuran / 20 °C

7.1: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

8.1: 910 mg / imidazole / CH₂Cl₂ / 2 h / Heating

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: tetrahydrofuran; hexane / 1 h / -78 °C

10.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h

11.1: toluene / 3.5 h / 110 °C

11.2: 64 percent / air / toluene / 2 h / 20 °C

12.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C

With 1,2,2,6,6-pentamethylpiperidine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dichloro bis(acetonitrile) palladium(II); N-Bromosuccinimide; n-butyllithium; formic acid; (1R,2R)-bis[2-(di-Ph-phosphinyl)-benzamino]-1,2-di-Ph-ethane; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; oxalic acid; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Heck cyclization / 6.2: Horner-Wadsworth-Emmons;

DOI:10.1021/ja0364118

upstream raw materials:

C₃₆H₃₂O₈

(2R,3R)-3-[(1E,3E)-(tert-butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-4-triisopropylsilanyloxy-2,3-dihydro-naphtho[1,2-b]furan-6,9-dione

2-iodoresorcinol

(2R,3S)-4-hydroxy-2,3-dimethyl-2,3-dihydro-benzofuran-3-carbonitrile