528853-82-9

Basic information

• Product Name: ethyl 2-(2-fluorobenzyl)-buta-2,3-dienoate
• Synonyms: ethyl 2-(2-fluorobenzyl)-buta-2,3-dienoate
• CAS NO: 528853-82-9
• Molecular Weight: 220.243
• Mol File: 528853-82-9.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2-(2-fluorobenzyl)-buta-2,3-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(2-fluorobenzyl)-buta-2,3-dienoate(528853-82-9)
• EPA Substance Registry System: ethyl 2-(2-fluorobenzyl)-buta-2,3-dienoate(528853-82-9)

Safety Data

• Hazardous Substances Data: 528853-82-9(Hazardous Substances Data)

Upstream product

• 75-36-5 acetyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 446-48-0 o-fluorobenzyl bromide 

Relevant articles and documents

An expedient phosphine-catalyzed [4 + 2] annulation: Synthesis of highly functionalized tetrahydropyridines

Ethyl 2-methyl-2,3-butadienoate acts as a 1,4-dipole synthon and undergoes [4 + 2] annulation with N-tosylimines in the presence of an organic phosphine catalyst. The resulting adducts, ethyl 6-substituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates, are formed in excellent yields with complete regioselectivity. Mechanistic reasoning for this new annulation has led to an expansion of the reaction scope by employing ethyl 2-(substituted-methyl)-2,3-butadienoates to give ethyl 2,6-cis-disubstituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates with high diastereoselectivities. Copyright

Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates

The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.

Phosphine-Catalyzed Enantioselective [4 + 3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles

With the use of a commercially available chiral phosphine as the catalyst, the first catalytic enantioselective [4 + 3] annulation of allenoates with C,N-cyclic azomethine imines is developed. The reaction works efficiently under mild reaction conditions to afford seven-membered ring-fused quinazoline-based tricyclic heterocycles in high yields with good to excellent diastereo- and enantioselectivities.

Small-molecule inhibitors of protein geranylgeranyltransferase type I

Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics. Copyright