syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide

Base Information

• Chemical Name: syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide
• CAS No.: 86941-59-5
• Deprecated CAS: 115225-74-6
• Molecular Formula: C20H18O3
• Molecular Weight: 306.3551
• DSSTox Substance ID: DTXSID60921661
• Nikkaji Number: J761.101C
• Wikidata: Q82894637
• Mol file: 86941-59-5.mol

Synonyms:syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide;1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol (1aalpha,2alpha,3beta,11calpha)-;86941-59-5;Benzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,11c-tetrahydro-6,11-dimethyl-, (1aalpha,2alpha,3beta,11calpha)-;DTXSID60921661;115225-74-6;6,11-Dimethyl-1a,2,3,11c-tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol

Chemical Property of syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide

Chemical Property:

• Vapor Pressure: 2.26E-14mmHg at 25°C
• Boiling Point: 581.7°C at 760 mmHg
• Flash Point: 305.6°C
• PSA: 52.99000
• Density: 1.387g/cm³
• LogP: 3.45760
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 306.125594432
• Heavy Atom Count: 23
• Complexity: 480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2C=CC3=C(C2=C(C4=CC=CC=C14)C)C5C(O5)C(C3O)O
• Isomeric SMILES: CC1=C2C=CC3=C(C2=C(C4=CC=CC=C14)C)[C@H]5[C@H](O5)[C@H]([C@@H]3O)O

Technology Process of syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide

There total 18 articles about syn-7,12-Dimethylbenz(a)anthracene-3,4-dihydrodiol 1,2-epoxide 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: 90.0%

2α-bromo-1β,3α,4β-trihydroxy-1,2,3,4-tetrahydro-7,12-dimethylbenzanthracene (103500-31-8) → trans-3,4-dihydroxy-syn-1,2-epoxy-1,2,3,4-tetrahydro-7,12-dimethylbenzanthracene (86941-59-5)

Guidance literature:

With potassium tert-butylate; tert-butyl alcohol; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo00368a021

Reference yield:

(3aR,4S,13aR)-13-Chloro-4-hydroxy-7,12-dimethyl-3a,4,13,13a-tetrahydro-1,3-dioxa-indeno[5,6-a]anthracen-2-one → 7,12-dimethylbenz[a]anthracene anti-diol epoxide (130856-45-0,74340-90-2,86941-58-4,86941-59-5,111001-45-7,111001-46-8,115225-74-6,135821-93-1,135911-40-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.25h; Yield given;

DOI:10.1021/ja00147a031

Reference yield:

(+/-)-trans-3,4-Dihydroxy-3,4-dihydro-7,12-dimethylbenzanthracene (68162-13-0,72617-60-8) → 7,12-dimethylbenz[a]anthracene anti-diol epoxide (130856-45-0,74340-90-2,86941-58-4,86941-59-5,111001-45-7,111001-46-8,115225-74-6,135821-93-1,135911-40-9)

Guidance literature:

With 3-chlorobenzoate; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/jo00368a021

upstream raw materials:

(+/-)-trans-3,4-Dihydroxy-3,4-dihydro-7,12-dimethylbenzanthracene

7,12-dimethylbenzanthracene-3,4-dione

3-hydroxy-7,12-dimethylbenzanthracene

3-oxo-1,2,3,4,5,6-hexahydrobenzo(a)anthracene

Downstream raw materials:

Phosphoric acid mono-{(2R,3S,5R)-3-hydroxy-5-[6-(2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydro-benzo[a]anthracen-1-ylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl} ester

Phosphoric acid mono-{(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-(2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydro-benzo[a]anthracen-1-ylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-2-ylmethyl} ester

(1S,2S,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-7,12-dimethyl-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol

(1S,2R,3S,4R)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-7,12-dimethyl-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol