(+)-(1S,2R,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene

Base Information

• Chemical Name: (+)-(1S,2R,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene
• CAS No.: 82510-57-4
• Molecular Formula: C₁₈H₁₄O₃
• Molecular Weight: 278.307
• Nikkaji Number: J511.688K

Synonyms:CCRIS 7368;3,4-Dihydroxy-1,2-epoxybenzo(c)phenanthrene;82510-57-4;(-)-Benzo(c)phenanthrene-3,4-diol-1,2-epoxide-2;(+)-anti-Benzo(c)phenanthrene-3,4-diol-1,2-epoxide;(+)-Benzo(c)phenanthrene-3,4-diol-1,2-epoxide (anti);(-)-anti-Benzo(c)phenanthrene-3,4-dihydrodiol-1,2-epoxide;(1S,2R,3R,4S)-(+)-anti-Benzo(c)phenanthrene-3,4-diol 1,2-epoxide;(+)-(1R,2S,3R,4S)-3,4-Dihydorxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(C)phenanthrene;Benzo(c)phenanthrene-3,4-diol, 1,2,3,4-tetrahydro-1,2-epoxy-, (E)-(-)-(1R,2S,3S,4R)-;trans-1-beta,2-beta-Epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene-3-beta,4-alpha-diol;(1aR-(1aalpha,2beta,3alpha,11dalpha))-1a,2,3,11d-tetrahydrobenzo(5,6)phenanthro(3,4-b)oxirene-2,3-diol;Benzo(5,6)phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,11d-tetrahydro-, (1aR,2R,3S,11dS)-;(+)-anti-BPhDE;B(c)PH diol epoxide-2;CCRIS 4191;SCHEMBL1278220;NIOSH/DI8520000;LS-38823;DI85200000;(+-)-B(c)PH-3,4-Diol-1,2-epoxide-2;(+-)-Benzo(c)phenanthrene-3,4-diol-1,2-epoxide-2;anti-(+-)-1,2,3,4-Tetrahydrobenzo(c)phenanthrene-3,4-diol-1,2-epoxide;(+-)-3-alpha,4-beta-Dihydroxy-1-alpha,2-alpha-epoxy-1,2,3,4-tetrahydrobenz(c)phenanthracene;(1AR-(1AALPHA,2BETA,3ALPHA,11DALPHA))-1A,2,3,11D-TETRAHYDROBENZO[5,6]PHENANTHRO[3,4-B]OXIRENE-2,3-DI OL;(3S,5R,6R,7S)-4-oxapentacyclo[9.8.0.0?,?.0?,?.0??,??]nonadeca-1(11),2(8),9,12,14(19),15,17-heptaene-6,7-diol;(3S,5R,6R,7S)-4-oxapentacyclo[9.8.0.02,8.03,5.014,19]nonadeca-1(11),2(8),9,12,14,16,18-heptaene-6,7-diol;Benzo(c)phenanthrene-3-alpha,4-beta-diol, 1,2,3,4-tetrahydro-1-alpha,2-alpha-epoxy-, (+-)-

Chemical Property of (+)-(1S,2R,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene

Chemical Property:

• Vapor Pressure: 1.03E-13mmHg at 25°C
• Boiling Point: 567.5°Cat760mmHg
• Flash Point: 297°C
• Density: 1.478g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 278.094294304
• Heavy Atom Count: 21
• Complexity: 425

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=C3)C(C(C5C4O5)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=C3)[C@@H]([C@H]([C@@H]5[C@H]4O5)O)O

Technology Process of (+)-(1S,2R,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene

There total 9 articles about (+)-(1S,2R,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene 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:

3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene (73093-19-3,79117-84-3,81345-49-5,86631-73-4,86631-74-5,88244-27-3) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrobenzophenanthrene (75410-89-8,75443-72-0,76024-59-4,76024-60-7,81371-24-6,82510-56-3,82510-57-4,82510-58-5,82510-59-6,111001-48-0,82373-05-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; for 2h;

DOI:10.1021/jo00265a023

Reference yield:

3-hydroxybenzophenanthrene (22717-95-9) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrobenzophenanthrene (75410-89-8,75443-72-0,76024-59-4,76024-60-7,81371-24-6,82510-56-3,82510-57-4,82510-58-5,82510-59-6,111001-48-0,82373-05-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.19 g / (KSO₃)2NO, Adogen 464, KH₂PO₄ / benzene / 1 h

2: 1.64 g / NaBH₄, O₂ / ethanol / 126 h

3: 33 mg / m-chloroperbenzoic acid / tetrahydrofuran / 2 h

With sodium tetrahydroborate; potassium dihydrogenphosphate; adogen 464; potassium nitrososulfonate; oxygen; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; benzene;

DOI:10.1021/jo00265a023

Reference yield:

benzophenanthrene-3,4-dione (118658-88-1) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrobenzophenanthrene (75410-89-8,75443-72-0,76024-59-4,76024-60-7,81371-24-6,82510-56-3,82510-57-4,82510-58-5,82510-59-6,111001-48-0,82373-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.64 g / NaBH₄, O₂ / ethanol / 126 h

2: 33 mg / m-chloroperbenzoic acid / tetrahydrofuran / 2 h

With sodium tetrahydroborate; oxygen; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00265a023

upstream raw materials:

3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene

3-hydroxybenzophenanthrene

benzophenanthrene-3,4-dione

3-hydroxybenzophenanthrene acetate

Downstream raw materials:

(3R,4S)-3,4-Dihydroxy-3,4-dihydro-1H-benzo[c]phenanthren-2-one

(1S,2R,3R,4S)-1,2,3,4-Tetrahydro-benzo[c]phenanthrene-1,2,3,4-tetraol

(1S,2S,3S,4R)-1,2,3,4-Tetrahydro-benzo[c]phenanthrene-1,2,3,4-tetraol

N²-[1-(2,3,4-trisbenzoyloxy-1,2,3,4-tetrahydrobenzo[c]phenanthrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

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