Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans-

Base Information

• Chemical Name: Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans-
• CAS No.: 81824-11-5
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.33
• DSSTox Substance ID: DTXSID601002251
• Wikidata: Q82996375
• Mol file: 81824-11-5.mol

Synonyms:81824-11-5;Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans-;(14S,15S)-pentacyclo[10.7.1.02,7.08,20.013,18]icosa-1(20),2,4,6,8,10,12,16,18-nonaene-14,15-diol;11,12-Dihydrobenz(e)acephenanthrylene-11,12-diol trans-;DTXSID601002251;11,12-Dihydrobenzo[e]acephenanthrylene-11,12-diol

Chemical Property of Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans-

Chemical Property:

• Vapor Pressure: 4.47E-13mmHg at 25°C
• Boiling Point: 553.3°Cat760mmHg
• Flash Point: 268.6°C
• PSA: 40.46000
• Density: 1.46g/cm³
• LogP: 3.90830
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 472

Purity/Quality:

trans-11,12-Dihydro-11,12-dihydroxybenzo[b]fluoranthene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC4=C5C(C(C=CC5=CC2=C43)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C3=CC=CC4=C5[C@@H]([C@H](C=CC5=CC2=C43)O)O
• Uses: Trans-11,12-Dihydro-11,12-dihydroxybenzo[b]fluoranthene is a mutagenic and and possible carcnogenic compound. It is used in biological study of tumeridenicity.

Technology Process of Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans-

There total 26 articles about Benz(e)acephenanthrylene-11,12-diol, 11,12-dihydro-, trans- 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: 32.0%

trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene (88746-68-3) → cis-11,12-dihydro-11,12-dihydroxybenzofluoranthene (81824-11-5,110607-47-1) + trans-11,12-dihydro-11,12-dihydroxybenzofluoranthene (81824-11-5)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 5 ℃; for 1h;

DOI:10.1021/jo00180a026

Reference yield: 32.0%

trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene (88746-68-3) → cis-11,12-dihydro-11,12-dihydroxybenzofluoranthene (81824-11-5,110607-47-1) + trans-11,12-dihydro-11,12-dihydroxybenzofluoranthene (81824-11-5)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 5 ℃; for 1h;

DOI:10.1021/jo00180a026

Reference yield:

2-methylfluoranthene (33543-31-6) → cis-11,12-dihydro-11,12-dihydroxybenzofluoranthene (81824-11-5,110607-47-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

2: 1.85 g / diethyl ether / 8 h

3: 1.) diborane, sodium hydroxide, 2.) H₂O₂ / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h

4: 82 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h

5: 62 percent / AgNO₃, NaOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

6: 1.8 g / oxalyl chloride / CH₂Cl₂ / 3 h / Ambient temperature

7: AlCl₃ / CS₂ / 1.) 0 deg C , 1h, 2.) reflux , 30 min

8: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature

9: 72 percent / HCl / acetic acid / 1 h / 90 °C

10: 60 percent / I₂ / benzene / 3 h / Heating

11: 60 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

12: 50 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

13: sodium methoxide / tetrahydrofuran; methanol / 1 h / 5 °C

With sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; Perbenzoic acid; oxalyl dichloride; DBN; dihydrogen peroxide; iodine; sodium methylate; silver nitrate; pyridinium chlorochromate; diborane; hydrogenchloride; In tetrahydrofuran; methanol; carbon disulfide; tetrachloromethane; diethyl ether; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00180a026

upstream raw materials:

trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene

2-methylfluoranthene

4-(2-fluoranthenyl)-1-butene

9,10-dihydrobenzofluoranthene

Refernces