Di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Base Information

• Chemical Name: Di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS No.: 39203-22-0
• Molecular Formula: C15H24N2O4
• Molecular Weight: 296.367
• NSC Number: 109945
• DSSTox Substance ID: DTXSID90296571
• Nikkaji Number: J1.096.169F
• Mol file: 39203-22-0.mol

Synonyms:39203-22-0;di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;NSC 109945;NSC109945;ditert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;DTXSID90296571;NSC-109945;2,3-Bis(tert-butoxycarbonyl)-2,3-diazabicyclo[2.2.1]hepta-5-ene;2,3-di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;Di(tert-butyl) 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property of Di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property:

• Vapor Pressure: 6.05E-05mmHg at 25°C
• Boiling Point: 345.7°C at 760 mmHg
• Flash Point: 162.9°C
• Density: 1.162g/cm³
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 296.17360725
• Heavy Atom Count: 21
• Complexity: 431

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CC(N1C(=O)OC(C)(C)C)C=C2

Technology Process of Di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

There total 5 articles about Di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 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: 100.0%

di-tert-butyl-diazodicarboxylate (870-50-8) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (39203-22-0)

Guidance literature:

In dichloromethane; at 0 ℃;

DOI:10.1021/jo011190e

Reference yield: 45.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + di-tert-butyl (E)-azodicarboxylate (870-50-8) → di-tert-butyl 1-(cyclopent-2-enyl)hydrazine-1,2-dicarboxylate + di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (39203-22-0)

Guidance literature:

With 1,1,3,3-Tetramethyldisiloxane; [N-salicylidene-2-aminoisobutyrato]-[2-aminoisobutyrato]Co; In ethanol; at 23 ℃; for 12h;

DOI:10.1021/ol0517473

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (39203-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrazine hydrate / methanol / Inert atmosphere

2: pyridine; bromine / dichloromethane / Inert atmosphere

3: dichloromethane / Inert atmosphere

With pyridine; bromine; hydrazine hydrate; In methanol; dichloromethane;

DOI:10.1021/ja309650u

upstream raw materials:

di-tert-butyl-diazodicarboxylate

cyclopenta-1,3-diene

di-tert-butyl (E)-azodicarboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

2,3-diaza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid di-tert butyl ester

2-trifluoroacetyl-2,3-diazabicyclo<2.2.1>heptane

(-)-di-tert-butyl 1-((1R,2S)-2-(phenylethynyl)cyclopent-3-enyl)hydrazine-1,2-dicarboxylate

(+/-)-trans-2-phenyl-cyclopentylamine