(3R,4R)-3,4-dihydrobenzo[k]tetraphene-3,4-diol

Base Information

• Chemical Name: (3R,4R)-3,4-dihydrobenzo[k]tetraphene-3,4-diol
• CAS No.: 74634-56-3
• Molecular Formula: C₂₂H₁₆O₂
• Molecular Weight: 312.368
• Mol file: 74634-56-3.mol

Synonyms:

Chemical Property of (3R,4R)-3,4-dihydrobenzo[k]tetraphene-3,4-diol

Chemical Property:

• Vapor Pressure: 1.52E-15mmHg at 25°C
• Boiling Point: 606.1°Cat760mmHg
• Flash Point: 289.5°C
• Density: 1.382g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3,4-dihydrobenzo[k]tetraphene-3,4-diol

There total 8 articles about (3R,4R)-3,4-dihydrobenzo[k]tetraphene-3,4-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: 44.0%

trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene (66267-19-4) → (-)-(3R,4R)-3,4-dihydroxy-3,4-dihydrodibenz[a,h]anthracene (1421-83-6,66267-19-4,72591-29-8,74634-56-3,105453-65-4,105453-64-3)

Guidance literature:

trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene; With silica-bound (-)-2-(2,5,9,11-tetranitro-7H-benzo[c]fluoren-7-ylideneaminooxy)propionic acid; In methanol; dichloromethane; Resolution of racemate;

With silica-bound (+)-2-(2,5,9,11-tetranitro-7H-benzo[c]fluoren-7-ylideneaminooxy)propionic acid; In methanol; dichloromethane; Resolution of racemate;

DOI:10.1021/tx200398b

Reference yield:

dibenzanthracene-3,4-quinone (70644-35-8) → cis-3,4-dihydroxy-3,4-dihydrodibenzanthracene (1421-83-6,66267-19-4,72591-29-8,74634-56-3,105453-64-3,105453-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / bromine / CHCl₃ / 0.5 h / Ambient temperature

2: 1.) sodium borohydride / 1.) tetrahydrofuran, 95percent ethanol, room temperature, 4 h, 2.) pyridine, room temperature, 15 h

3: saturated methanolic ammonia / 5 h / Ambient temperature

With sodium tetrahydroborate; ammonia; bromine; In chloroform;

Reference yield:

trans-3,4-bis(benzoyloxy)-1,2,3,4-tetrahydrodibenzanthracene (72378-84-8) → (-)-(3R,4R)-3,4-dihydroxy-3,4-dihydrodibenz[a,h]anthracene (1421-83-6,66267-19-4,72591-29-8,74634-56-3,105453-65-4,105453-64-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 0.67 h / 60 °C / UV-irradiation; Reflux

2.1: lithium carbonate; lithium chloride / N,N,N,N,N,N-hexamethylphosphoric triamide / 2.5 h / 100 °C / Inert atmosphere

3.1: methanol

4.1: silica-bound (-)-2-(2,5,9,11-tetranitro-7H-benzo[c]fluoren-7-ylideneaminooxy)propionic acid / methanol; dichloromethane / Resolution of racemate

4.2: silica-bound (+)-2-(2,5,9,11-tetranitro-7H-benzo[c]fluoren-7-ylideneaminooxy)propionic acid / Resolution of racemate

With methanol; N-Bromosuccinimide; lithium carbonate; lithium chloride; dibenzoyl peroxide; In methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/tx200398b

upstream raw materials:

trans-3,4-bis(benzoyloxy)-1,2,3,4-tetrahydrodibenzanthracene

trans-3,4-bis(benzoyloxy)-3,4-dihydrodibenzanthracene

C₃₆H₂₅BrO₄

trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene

Downstream raw materials:

(-)-(1S,2R,3R,4S)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrodibenz[a,h]anthracene

Refernces

• 1、 Kundu, Nitya G.. "Reduction of ortho-Quinones to Dihydrodiols". . p. 1920 - 1923. Retrieved 2007/10/02.