(-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol

Base Information

• Chemical Name: (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol
• CAS No.: 118357-18-9
• Molecular Formula: C₄₈H₃₈O₂
• Molecular Weight: 646.829
• Mol file: 118357-18-9.mol

Synonyms:

Chemical Property of (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol

There total 16 articles about (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol 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:

methyl 3-(3,4-dimethoxyphenyl)propionate (27798-73-8) → (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol (118357-18-9)

Guidance literature:

Multi-step reaction with 13 steps

1: stannic chloride / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) RT, 15 min

2: 1.) sodium hydride / 1.) THF, 2.) reflux, 3 h

3: NaOH / methanol; H₂O / 5 h / Heating

4: 30 h / 200 °C

5: conc. H₂SO₄ / 4 h / Heating

6: 72 percent / FeCl₃, Br₂ / CCl₄ / Heating

7: aq. NaOH / aq. ethanol / 2 h / Heating

8: t-BuLi / tetrahydrofuran; hexane / 20 h / -78 °C

10: 48 percent / triethylsilane, trifluoroacetic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

11: 90 percent / boron tribromide / CH₂Cl₂ / 12 h / -78 - 20 °C

12: 39 percent / pyridine / 96 h / Ambient temperature

13: lithium aluminum hydride / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

With pyridine; triethylsilane; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; bromine; tert.-butyl lithium; boron tribromide; iron(III) chloride; tin(IV) chloride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water;

DOI:10.1021/jo00265a049

Reference yield:

methyl 3-<2-(chloromethyl)-4,5-dimethoxyphenyl>-propanoate (118357-03-2) → (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol (118357-18-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) sodium hydride / 1.) THF, 2.) reflux, 3 h

2: NaOH / methanol; H₂O / 5 h / Heating

3: 30 h / 200 °C

4: conc. H₂SO₄ / 4 h / Heating

5: 72 percent / FeCl₃, Br₂ / CCl₄ / Heating

6: aq. NaOH / aq. ethanol / 2 h / Heating

7: t-BuLi / tetrahydrofuran; hexane / 20 h / -78 °C

9: 48 percent / triethylsilane, trifluoroacetic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

10: 90 percent / boron tribromide / CH₂Cl₂ / 12 h / -78 - 20 °C

11: 39 percent / pyridine / 96 h / Ambient temperature

12: lithium aluminum hydride / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

With pyridine; triethylsilane; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; bromine; tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water;

DOI:10.1021/jo00265a049

Reference yield:

3-<2-(2-carboxyethyl)-4,5-dimethoxyphenyl>propanoic acid (118357-06-5) → (-)-3,6-bis(3,5-diphenylphenyl)-1,2,3,6,7,8-hexahydro-as-indacene-4,5-diol (118357-18-9)

Guidance literature:

Multi-step reaction with 9 steps

1: conc. H₂SO₄ / 4 h / Heating

2: 72 percent / FeCl₃, Br₂ / CCl₄ / Heating

3: aq. NaOH / aq. ethanol / 2 h / Heating

4: t-BuLi / tetrahydrofuran; hexane / 20 h / -78 °C

6: 48 percent / triethylsilane, trifluoroacetic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 90 percent / boron tribromide / CH₂Cl₂ / 12 h / -78 - 20 °C

8: 39 percent / pyridine / 96 h / Ambient temperature

9: lithium aluminum hydride / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

With pyridine; triethylsilane; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; bromine; tert.-butyl lithium; boron tribromide; iron(III) chloride; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane;

DOI:10.1021/jo00265a049

upstream raw materials:

3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 3,6-bis-[1,1';3',1'']terphenyl-5'-yl-5-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,6,7,8-hexahydro-as-indacen-4-yl ester

3,5-diphenylcyclohex-2-en-1-one

methyl 3-(3,4-dimethoxyphenyl)propionate

N'-phenyl-(1,1';3',1'-terphenyl)-5'-amine