2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine

Base Information

• Chemical Name: 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine
• CAS No.: 1381787-78-5
• Molecular Formula: C₂₉H₂₆N₂S₂
• Molecular Weight: 466.671
• Mol file: 1381787-78-5.mol

Synonyms:2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine

Chemical Property of 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine

There total 5 articles about 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine 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: 61.0%

diphenyldisulfane (882-33-7) + (+/-)-4,10-dibromo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (614290-27-6,1042269-17-9,1042269-27-1) → 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (1381787-78-5)

Guidance literature:

(+/-)-4,10-dibromo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

diphenyldisulfane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1039/c2dt30509g

Reference yield: 61.0%

(SS,SS,5R,11R)-2,8-dimethyl-4,10-bis(p-tolylsulfinyl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (1619230-61-3,1619230-62-4) + diphenyldisulfane (882-33-7) → (5R,11R)-2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (1381787-78-5,1619230-56-6)

Guidance literature:

(S_S,S_S,5R,11R)-2,8-dimethyl-4,10-bis(p-tolylsulfinyl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine; With n-butyllithium; iodobenzene; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

diphenyldisulfane; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4cc03963g

Reference yield:

2-bromo-p-toluidine (583-68-6) → 2,8-dimethyl-4,10-bis(phenylthio)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (1381787-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

2.2: 20 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; trifluoroacetic acid;

DOI:10.1039/c2dt30509g

upstream raw materials:

2-bromo-p-toluidine

diphenyldisulfane

(+/-)-4,10-dibromo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate