2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-

Base Information

• Chemical Name: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-
• CAS No.: 955-02-2
• Molecular Formula: C14H20N2O
• Molecular Weight: 232.326

Synonyms:

Chemical Property of 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-

There total 4 articles about 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)- 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: 45.0%

2,6-di-tert-butyl-4-aminophenol (950-58-3) → 2,6-di-tert-butyl-4-diazo-2,5-cyclohexadien-1-one (955-02-2)

Guidance literature:

2,6-di-tert-butyl-4-aminophenol; With hydrogenchloride; In ethanol; water; at 0 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

With sodium nitrite; In ethanol; water; at 0 ℃; for 2.16667h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201800648

Reference yield:

2,6-di-tert-butyl-1,4-benzoquinone 4-p-tosylhydrazone (94999-56-1) → 2,6-di-tert-butyl-4-diazo-2,5-cyclohexadien-1-one (955-02-2)

Guidance literature:

DOI:10.1021/jo951738f

Reference yield:

2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) → 2,6-di-tert-butyl-4-diazo-2,5-cyclohexadien-1-one (955-02-2)

Guidance literature:

DOI:10.1021/jo951738f

upstream raw materials:

2,6-di-tert-butyl-1,4-benzoquinone 4-p-tosylhydrazone

2,6-Di-tert-butyl-1,4-benzoquinone

2,6-di-tert-butyl-4-aminophenol

Downstream raw materials:

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl

2,6-di-tert-butyl-4-cyclohexylphenol

2,6-Di-tert-butyl-1,4-benzoquinone

Refernces

Generation of a small library of highly electron-rich 2-(hetero)aryl- substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue

10.1002/ejoc.200400213

The research focuses on the synthesis of a small library of highly electron-rich 2-aryl and 2-heteroaryl phenethylamines (PEAs) using the Suzuki-Miyaura cross-coupling reaction, which is enhanced by microwave irradiation for improved reaction yield and speed. The study commenced with the synthesis of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate from 2-(3,4-dimethoxyphenyl)ethylamine, followed by its coupling with various boronic acids to generate the PEAs. The reactions were optimized using sodium hydrogencarbonate as the base and tetrakis(triphenylphosphane)palladium(0) as the catalyst, with the mixture of N,N-dimethylformamide and water as the solvent. The synthesized compounds were characterized by 1H and 13C NMR spectroscopy, and low-resolution mass spectrometry (LR-MS) to confirm their structures and purities. The research also successfully extended this methodology to synthesize an apogalanthamine analogue, a complex natural product with significant biological activities, showcasing the versatility and efficacy of the developed synthetic strategy.

Photochemical syntheses of apogalanthamine analogs as αadrenergic blocking agents

10.1248/cpb.26.155

The research focuses on the photochemical syntheses of apogalanthamine analogs, specifically 10,11-methylenedioxy- and 10,11-dimethoxy-5,6,7,8-tetrahydrodibenz[e,e]azocines (1 and 2, respectively), which have α-adrenergic blocking activities. These compounds were synthesized by photolysis of N-benzyl-2-iodo-4,5-methylenedioxy- and N-benzyl-2-iodo-4,5-dimethoxy-β-phenethylamine (20 and 21, respectively). Other related compounds, such as 2,3-methylenedioxy- and 2,3-dimethoxy-5,6,7,8-tetrahydrodibenz[c,e]azocine (9 and 10, respectively), were also synthesized from similar precursors. The study found that the yields of 9 and 10, synthesized from iodo-amines with an iodine atom in the benzyl group, were better than those of 1 and 2, which were synthesized from iodides with a halogen atom in the phenethyl group.

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