14011-60-0

Basic information

• Product Name: Diethyl-2,3-diazabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylate
• Synonyms: Diethyl-2,3-diazabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylate;Diethyl-2,3-diazabicyclo[2,2,1]hep tert-5-ene-2,3-dicarboxylate
• CAS NO: 14011-60-0
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 238.23986
• Mol File: 14011-60-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 305.7°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• Density: 1.272g/cm³
• Vapor Pressure: 0.000807mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: Diethyl-2,3-diazabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl-2,3-diazabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylate(14011-60-0)
• EPA Substance Registry System: Diethyl-2,3-diazabicyclo[2,2,1]hept-5-ene-2,3-dicarboxylate(14011-60-0)

Safety Data

• Hazardous Substances Data: 14011-60-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16N2O4/c1-3-16-10(14)12-8-5-6-9(7-8)13(12)11(15)17-4-2/h5-6,8-9H,3-4,7H2,1-2H3

Upstream product

• 4143-60-6 Diethyl azodicarboxylate 
• 542-92-7 cyclopenta-1,3-diene 
• 4143-61-7 diethyl diazodicarboxylate 
• 71-43-2 benzene 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 1042726-24-8 diethyl 1-((1R,2S)-2-(phenylethynyl)cyclopent-3-enyl)hydrazine-1,2-dicarboxylate 

Relevant articles and documents

Heavy-Atom Tunneling Processes during Denitrogenation of 2,3-Diazabicyclo[2.2.1]hept-2-ene and Ring Closure of Cyclopentane-1,3-diyl Diradical. Stereoselectivity in Tunneling and Matrix Effect

Triplet cyclopentane-1,3-diyl diradical (T-DR) was generated via photolysis of 2,3-diazabicyclo[2.2.1]hept-2-ene (AZ) under low-temperature matrix conditions. Temperature independency of T-DR decay and the kinetic isotope effect of T-DR-d6 provided experimental evidence in favor of heavy-atom (carbon) tunneling process during the decay of T-DR to bicyclo[2.1.0]pentane (CP) via singlet S-DR. For the first time, the formation of CP was confirmed using low-temperature infrared spectra. Computations of the heavy-atom tunneling process using the small-curvature tunneling method demonstrated a fast reaction from S-DR to CP. Moreover, we observed heavy-atom tunneling during denitrogenation of AZ. Stereoselectivity in the tunneling process of T-DR-d6 was observed at 7 K to form retention-CP-d6 in higher amounts compared to inversion-CP-d6. Photolysis of AZ-d6 yielded inv-CP-d6 and ret-CP-d6 in environment- and temperature-dependent ratios. Moreover, because of the prominent matrix effect, T-DR decayed more rapidly in Ar than in glassy organic matrices.

An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides

A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4- hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).

Enantioselective desymmetrization of meso bicyclic hydrazines: A novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores

Catalytic asymmetric hydroboration can be successfully applied to meso bicyclic hydrazines. The resulting alcohols are of great synthetic interest and can lead in a straightforward manner to cyclopentanic diamino alcohols with good enantiomeric purity.