(2S,3S)-2,3-dihydrobenzo[j]fluoranthene-2,3-diol

Base Information

• Chemical Name: (2S,3S)-2,3-dihydrobenzo[j]fluoranthene-2,3-diol
• CAS No.: 106542-80-7
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.33
• Mol file: 106542-80-7.mol

Synonyms:trans-4,5-Dihydro-4,5-dihydroxybenzo[j]fluoranthene

Chemical Property of (2S,3S)-2,3-dihydrobenzo[j]fluoranthene-2,3-diol

Chemical Property:

• Vapor Pressure: 1.12E-13mmHg at 25°C
• Boiling Point: 566.6°Cat760mmHg
• Flash Point: 275.4°C
• Density: 1.43g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S)-2,3-dihydrobenzo[j]fluoranthene-2,3-diol

There total 17 articles about (2S,3S)-2,3-dihydrobenzo[j]fluoranthene-2,3-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: 84.0%

Acetic acid (4S,5S)-5-acetoxy-4,5-dihydro-benzo[j]fluoranthen-4-yl ester (106521-03-3,106521-06-6) → trans-4,5-dihydro-4,5-dihydroxybenzofluoranthene (106542-80-7,151258-40-1)

Guidance literature:

With methanol; ammonia; for 96h; Ambient temperature;

DOI:10.1021/jo00381a025

Reference yield:

9-methoxy-11H-benzofluorene (6235-04-7) → trans-4,5-dihydro-4,5-dihydroxybenzofluoranthene (106542-80-7,151258-40-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) ether, hexane, -30 deg C, 1 h, 2.) ether, hexane, from -30 deg C to RT

2: 69 percent / conc,. H₂SO₄ / benzene / 20 h / Heating

3: 96 percent / 10 N NaOH / pyridine / 3 h / Ambient temperature

4: 97 percent / 10 N NaOH / ethanol / 17 h / Heating

5: 70 percent / methanesulfonic acid / 19 h / Ambient temperature

6: NaBH₄ / methanol / 0.67 h / Ambient temperature

7: p-toluenesulfonic acid / benzene / 2 h / Heating

8: 100 percent / 1-methylnaphthalene / benzene / 7 h / Heating

9: 96 percent / BBr₃ / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) RT, 2 h

10: 94 percent / Adogen 464, potassium nitrosodisulfonate, 1/6 M KH₂PO₄ / benzene; H₂O / 2 h / Ambient temperature

11: 1.) KBH₄, 2.) pyridine / 1.) ethanol, 21 h, 2.) 0 deg C, overnight

12: 84 percent / ammonia, methanol / 96 h / Ambient temperature

With pyridine; methanol; sodium hydroxide; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; potassium borohydride; adogen 464; methanesulfonic acid; potassiuim nitrosodisulfonate; sulfuric acid; ammonia; boron tribromide; toluene-4-sulfonic acid; 1-Methylnaphthalene; In pyridine; methanol; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo00381a025

Reference yield:

phenyl 2-methoxy-1-naphthoate (106542-96-5) → trans-4,5-dihydro-4,5-dihydroxybenzofluoranthene (106542-80-7,151258-40-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 68 percent / diethyl ether; benzene / 1.) reflux, 3 h, 2.) RT, overnight

2: 100 percent / methanesulfonic acid / 1.5 h / Ambient temperature

3: 59 percent / zinc amalgam, conc. HCl / toluene; acetic acid / 27 h / Heating

4: 1.) n-BuLi / 1.) ether, hexane, -30 deg C, 1 h, 2.) ether, hexane, from -30 deg C to RT

5: 69 percent / conc,. H₂SO₄ / benzene / 20 h / Heating

6: 96 percent / 10 N NaOH / pyridine / 3 h / Ambient temperature

7: 97 percent / 10 N NaOH / ethanol / 17 h / Heating

8: 70 percent / methanesulfonic acid / 19 h / Ambient temperature

9: NaBH₄ / methanol / 0.67 h / Ambient temperature

10: p-toluenesulfonic acid / benzene / 2 h / Heating

11: 100 percent / 1-methylnaphthalene / benzene / 7 h / Heating

12: 96 percent / BBr₃ / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) RT, 2 h

13: 94 percent / Adogen 464, potassium nitrosodisulfonate, 1/6 M KH₂PO₄ / benzene; H₂O / 2 h / Ambient temperature

14: 1.) KBH₄, 2.) pyridine / 1.) ethanol, 21 h, 2.) 0 deg C, overnight

15: 84 percent / ammonia, methanol / 96 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; potassium dihydrogenphosphate; amalgamated zinc; n-butyllithium; potassium borohydride; adogen 464; methanesulfonic acid; potassiuim nitrosodisulfonate; sulfuric acid; ammonia; boron tribromide; toluene-4-sulfonic acid; 1-Methylnaphthalene; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; toluene; benzene;

DOI:10.1021/jo00381a025

upstream raw materials:

benzofluoranthene-4,5-dione

Acetic acid (4S,5S)-5-acetoxy-4,5-dihydro-benzo[j]fluoranthen-4-yl ester

9-methoxy-11H-benzofluorene

phenyl 2-methoxy-1-naphthoate

Downstream raw materials:

trans-4,5-dihydroxy-syn-6,6a-epoxy-4,5,6,6a-tetrahydrobenzofluoranthene

trans-4,5-dihydroxy-anti-6,6a-epoxy-4,5,6,6a-tetrahydrobenzofluoranthene

Refernces

• 1、 Rice, Joseph E.,Shih, Hsien-Cheng,Hussain, Nalband,LaVoie, Edmond J.. "Synthesis of the Major Metabolic Dihydrodiols of Benzofluoranthene". . p. 849 - 855. Retrieved 2007/10/02.