rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol

Base Information

• Chemical Name: rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol
• CAS No.: 80433-78-9
• Deprecated CAS: 64598-81-8
• Molecular Formula: C18H14O3
• Molecular Weight: 278.302
• DSSTox Substance ID: DTXSID901120343
• Nikkaji Number: J1.261.993F
• Mol file: 80433-78-9.mol

Synonyms:80433-78-9;63493-01-6;rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol;1a,2,3,11c-Tetrahydrobenzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol (1aalpha,2alpha,3beta,11calpha)-;1a,2,3,11c-Tetrahydrobenzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol (1aR-(1aalpha,2alpha,3beta,11calpha))-;Benzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,11c-tetrahydro-, (1aalpha,2alpha,3beta,11calpha)-;Benzo(6,7)phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,11c-tetrahydro-, (1aR-(1aalpha,2alpha,3beta,11calpha))-;Benzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol, 1a,2,3,11c-tetrahydro-, [1aR-(1aalpha,2alpha,3beta,11calpha)]-;NIOSH/CW4640250;DTXSID901120343;CW46402500;1,2,3,4-Tetrahydro-1alpha,2alpha-epoxybenzo[a]anthracene-3beta,4alpha-diol;(-)-(1S,2R,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene;Benz(a)anthracene-3-beta,4-alpha-diol, 1,2,3,4-tetrahydro-1-alpha,2-alpha-epoxy-, (-)-

Chemical Property of rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol

Chemical Property:

• Vapor Pressure: 1.03E-13mmHg at 25°C
• Boiling Point: 567.5°Cat760mmHg
• Flash Point: 297°C
• PSA: 52.99000
• Density: 1.478g/cm³
• LogP: 2.84080
• XLogP3: 2
• 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:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C=CC4=C3C5C(O5)C(C4O)O
• Isomeric SMILES: C1=CC=C2C=C3C(=CC2=C1)C=CC4=C3[C@H]5[C@H](O5)[C@H]([C@@H]4O)O

Technology Process of rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol

There total 10 articles about rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-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:

→ C18H14O3 (63438-26-6,63493-01-6,64551-89-9,64598-80-7,64598-81-8,80433-78-9,80433-79-0,80433-81-4,80446-23-7)

Guidance literature:

entspr. Dihydrodiol, 1) N-Bromacetamid, 2) Amberlit (OH-Form); Geschwindigkeitskonstante;

Reference yield:

(+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene (60967-89-7,64501-86-6,60839-18-1,67335-42-6,67335-43-7) → (-)-(1S,2R,3S,4R)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzanthracene (80433-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 19 percent / pyridine / 0 - 5 °C

2: 95 percent / NaOCH₃ / methanol; tetrahydrofuran / 1 h / Ambient temperature

3: 1.) N-bromoacetamide, 2.) Amberlite IRA-400 (hydroxide form) / 1.) THF, H₂O, room temp., 48 h, 2.) THF, 20 h

With pyridine; Amberlite IRA-400 (hydroxide form); sodium methylate; N-bromoacetamide; In tetrahydrofuran; methanol;

DOI:10.1021/jo00345a043

Reference yield:

(+/-)-trans-3,4-dihydroxy-1,2,3,4-tetrahydrobenzanthracene (60968-10-7,80399-21-9,80433-83-6,80433-84-7) → (-)-(1S,2R,3S,4R)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzanthracene (80433-78-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 35.8 percent / pyridine / Ambient temperature

2: 100 percent / NaOCH₃ / methanol; tetrahydrofuran / 1 h / Ambient temperature

3: 95 percent / pyridine / Ambient temperature

4: 94 percent / N-bromosuccinimide (NBS), α,α'-azobis(isobutyronitrile) (AIBN) / CCl4 / 0.5 h / 65 °C

5: 65 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 2.5 h / Ambient temperature

6: 83.5 percent / NH₃, CH₃OH / tetrahydrofuran

7: 1.) N-bromoacetamide, 2.) Amberlite IRA-400 (hydroxide form) / 1.) THF, H₂O, room temp., 48 h, 2.) THF, 20 h

With pyridine; methanol; N-Bromosuccinimide; Amberlite IRA-400 (hydroxide form); azobisisobutyronitrile; ammonia; sodium methylate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; N-bromoacetamide; In tetrahydrofuran; methanol; tetrachloromethane;

DOI:10.1021/jo00345a043

upstream raw materials:

(-)-trans-(3R,4R)-3,4-dihydroxy-3,4-dihydrobenzanthracene

(+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene

(+/-)-trans-3,4-dihydroxy-1,2,3,4-tetrahydrobenzanthracene

(+)-trans-(3R,4R)-3,4-dihydroxy-1,2,3,4-tetrahydrobenzanthracene

Refernces