(1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine

Base Information

• Chemical Name: (1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine
• CAS No.: 93780-95-1
• Molecular Formula: C₂₁H₁₅NO₃
• Molecular Weight: 329.355
• DSSTox Substance ID: DTXSID101034386
• Nikkaji Number: J1.454.927G
• Mol file: 93780-95-1.mol

Synonyms:93780-95-1;(1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(c,h)acridine;CCRIS 2353;[1R,2S,3S,4R]-3,4-DIHYDROXY-1,2-EPOXY-1,2,3,4-TETRAHYDROBENZ[C,H]ACRIDINE;(1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine;Benz(c)oxireno(5,6)benz(1,2-h)acridine-2,3-diol, 1a,2,3,13c-tetrahydro-, (1aS-(1a-alpha,2-beta,3-alpha,13c-alpha))-;DTXSID101034386

Chemical Property of (1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine

Chemical Property:

• Vapor Pressure: 3.42E-18mmHg at 25°C
• Boiling Point: 657.7°Cat760mmHg
• Flash Point: 351.5°C
• PSA: 65.88000
• Density: 1.527g/cm³
• LogP: 3.38900
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 329.10519334
• Heavy Atom Count: 25
• Complexity: 541

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Experimental carcinogenic data reported.
• Hazard Codes: Experimental carcinogenic data reported.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC4=C(C5=C(C=C4)C(C(C6C5O6)O)O)N=C32
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC3=CC4=C(C5=C(C=C4)[C@H]([C@@H]([C@H]6[C@@H]5O6)O)O)N=C32

Technology Process of (1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine

There total 10 articles about (1R,2S,3S,4R)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz(c,h)acridine 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: 78.0%

(-)-trans-(3R,4R)-3,4-dihydroxy-3,4-dihydrodibenzacridine (93780-91-7) → (1R,2S,3S,4R)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenzacridine (93780-95-1,93780-94-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo00201a019

Reference yield:

α-naphthol (90-15-3) → (1R,2S,3S,4R)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenzacridine (93780-95-1,93780-94-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 12.9 percent / 0.25 h / 250 °C

3: 88 percent / 25percent aq. NaOH / tetrahydrofuran; methanol / 5 h / Ambient temperature

4: 92 percent / pyridine / 24 h / Ambient temperature

5: 96 percent / NBS, AIBN / CCl₄ / 0.25 h / 60 - 62 °C

6: 66 percent / Li₂CO₃, LiF / hexamethylphosphoric acid triamide / 3 h / 85 - 90 °C

7: 93 percent / NH₃ / methanol; tetrahydrofuran / 4 h / Ambient temperature

9: 78 percent / m-chloroperbenzoic acid / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); ammonia; lithium carbonate; lithium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00201a019

Reference yield:

trans-3,4-dihydroxy-1,2,3,4-tetrahydrodibenzacridine (124508-39-0) → (1R,2S,3S,4R)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenzacridine (93780-95-1,93780-94-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / pyridine / 24 h / Ambient temperature

2: 96 percent / NBS, AIBN / CCl₄ / 0.25 h / 60 - 62 °C

3: 66 percent / Li₂CO₃, LiF / hexamethylphosphoric acid triamide / 3 h / 85 - 90 °C

4: 93 percent / NH₃ / methanol; tetrahydrofuran / 4 h / Ambient temperature

6: 78 percent / m-chloroperbenzoic acid / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); ammonia; lithium carbonate; lithium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00201a019

upstream raw materials:

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

α-naphthol

trans-3,4-dihydroxy-1,2,3,4-tetrahydrodibenzacridine

1-amino-5,6,7,8-tetrahydronaphthalene

Refernces