329363-13-5

Basic information

• Product Name: ethyl (Z)-4-oxo-2-cyclopentenylideneacetate
• CAS NO: 329363-13-5
• Molecular Weight: 166.177
• Mol File: 329363-13-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl (Z)-4-oxo-2-cyclopentenylideneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (Z)-4-oxo-2-cyclopentenylideneacetate(329363-13-5)
• EPA Substance Registry System: ethyl (Z)-4-oxo-2-cyclopentenylideneacetate(329363-13-5)

Safety Data

• Hazardous Substances Data: 329363-13-5(Hazardous Substances Data)

Upstream product

• 77341-51-6 (+/-)-4-benzoyloxy-2-cyclopentenone 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 329363-21-5 (+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate 

Relevant articles and documents

Five-membered ring analogues of shikimic acid

Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogues of shikimic acid. Enzymatic studies showed that analogues 1-3 are indeed processed by shikimate kinase to give phosphates 1-P, 2-P, and 3-P as five-membered ring analogues of shikimate-3-phosphate. In particular, analogue 1 is converted by the enzyme at a rate only 3.5-fold slower than that of the native substrate, while analogue 3 binds to shikimate kinase with an apparent Km of 1.7 mM, compared to 0.14 mM for shikimate.