1263291-39-9

Basic information

• Product Name: Ethyl (1α,8α,9β)-bicyclo[6.1.0]non-4-ene-9-carboxylate
• Synonyms: Ethyl (1R,8S,9s)-bicyclo[6.1.0]non-4-ene-9-carboxylate
• CAS NO: 1263291-39-9
• Molecular Weight: 0
• Mol File: 1263291-39-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Ethyl (1α,8α,9β)-bicyclo[6.1.0]non-4-ene-9-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (1α,8α,9β)-bicyclo[6.1.0]non-4-ene-9-carboxylate(1263291-39-9)
• EPA Substance Registry System: Ethyl (1α,8α,9β)-bicyclo[6.1.0]non-4-ene-9-carboxylate(1263291-39-9)

Safety Data

• Hazardous Substances Data: 1263291-39-9(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 1263166-90-0 (1R,8S,9S)‐bicyclo[6.1.0]non‐4‐yn‐9‐ylmethanol 
• 374898-56-3 C₁₀H₁₆O 

Relevant articles and documents

Bicyclo[6.1.0]nonyne and tetrazine amino acids for Diels-Alder reactions

Here we report a general method for the de novo synthesis of a bicyclo[6.1.0]nonyne group containing an amino acid, and used Marfey's reagent for chiral analysis. This unnatural amino acid offered exceptional reactivity in the inverse electron demand Diels-Alder cycloaddition with tetrazine containing amino acids. The subsequent selective labeling of living cells at low dye concentrations demonstrated the usefulness of the new amino acid for future imaging studies. This work also laid the foundation for introducing this unnatural amino acid into peptides based on the solid-phase synthesis method.

Synthesis of a toolbox of clickable rhodamine B derivatives

Abstract An efficient method for the large-scale preparation of rhodamine B clickable derivatives has been developed. Starting from inexpensive rhodamine B as the starting material it was possible to functionalize the carboxylic functionality of rhodamine B with an azide, a strained-alkyne, a substituted triphenylphosphine, a thiol, and a maleimide. Through the synthetic strategy it was possible to obtain stable and pure clickable rhodamine compounds that can be readily used not only for chemoselectively probing biomolecules, but also for materials science.

FUSED CYCLOOCTYNE COMPOUNDS AND THEIR USE IN METAL-FREE CLICK REACTIONS

The invention relates to fused cyclooctyne compounds, and to a method for their preparation. The invention also relates to a conjugate wherein a fused cyclooctyne compound according to the invention is conjugated to a label,and to the use of these conjugates in bioorthogonal labeling, imaging and/or modification, such as for example surface modification,of a target molecule. The invention further relates to a method for the modification of a target molecule, wherein a conjugate according to the invention is reacted with a compound comprising a 1,3-dipole or a 1,3-(hetero)diene.