(-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Base Information

• Chemical Name: (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine
• CAS No.: 1316274-00-6
• Molecular Formula: C₂₀H₁₇NO
• Molecular Weight: 287.361
• Mol file: 1316274-00-6.mol

Synonyms:(-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Chemical Property of (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

There total 6 articles about (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine 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:

(Z)-11-methyl-2-phenyldibenzo[b,f][1,4]oxazepine (1316273-90-1) → (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine (1316274-00-6) + (R)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S,S)-Xyl-C₃*-TunePhos; hydrogen; morpholin hydrochloride; In dichloromethane; at 20 ℃; for 20h; under 36201.3 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c1cc12263k

Reference yield:

4-phenyl-1-(2-nitrophenoxy)benzene (153815-63-5) → (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine (1316274-00-6) + (R)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Guidance literature:

Multi-step reaction with 4 steps

1: 5% Pd(II)/C(eggshell); hydrogen; acetic acid / ethanol / 12 h / 3102.97 Torr

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: trichlorophosphate / dichloromethane / 3 h / 120 °C / Inert atmosphere

4: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S,S)-Xyl-C₃*-TunePhos; hydrogen; morpholin hydrochloride / dichloromethane / 20 h / 20 °C / 36201.3 Torr

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S,S)-Xyl-C₃*-TunePhos; 5% Pd(II)/C(eggshell); hydrogen; morpholin hydrochloride; acetic acid; triethylamine; trichlorophosphate; In ethanol; dichloromethane;

DOI:10.1039/c1cc12263k

Reference yield:

ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → (-)-(S)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine (1316274-00-6) + (R)-11-methyl-2-phenyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

1.2: 13 h / 20 - 50 °C / Inert atmosphere

2.1: 5% Pd(II)/C(eggshell); hydrogen; acetic acid / ethanol / 12 h / 3102.97 Torr

3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: trichlorophosphate / dichloromethane / 3 h / 120 °C / Inert atmosphere

5.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S,S)-Xyl-C₃*-TunePhos; hydrogen; morpholin hydrochloride / dichloromethane / 20 h / 20 °C / 36201.3 Torr

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S,S,S)-Xyl-C₃*-TunePhos; 5% Pd(II)/C(eggshell); hydrogen; morpholin hydrochloride; sodium hydride; acetic acid; triethylamine; trichlorophosphate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c1cc12263k

upstream raw materials:

N-[2-([1,1'-biphenyl]-4-yloxy)phenyl]acetamide

(Z)-11-methyl-2-phenyldibenzo[b,f][1,4]oxazepine

4-Phenylphenol

4-phenyl-1-(2-nitrophenoxy)benzene