705250-77-7

Basic information

• Product Name: 3-[3,5-bis(trifluoromethyl)phenyl]-2(Z)-propenoic acid methyl ester
• Synonyms: 3-[3,5-bis(trifluoromethyl)phenyl]-2(Z)-propenoic acid methyl ester
• CAS NO: 705250-77-7
• Molecular Weight: 298.185
• Mol File: 705250-77-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-[3,5-bis(trifluoromethyl)phenyl]-2(Z)-propenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[3,5-bis(trifluoromethyl)phenyl]-2(Z)-propenoic acid methyl ester(705250-77-7)
• EPA Substance Registry System: 3-[3,5-bis(trifluoromethyl)phenyl]-2(Z)-propenoic acid methyl ester(705250-77-7)

Safety Data

• Hazardous Substances Data: 705250-77-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 155814-20-3 trans-3,5-di(trifluoromethyl)cinnamic acid 
• 328-72-3 3,5-(bistrifluoromethyl)chlorobenzene 
• 32673-25-9 di(tertbutyl)phenylphosphine 
• 19293-63-1 dicyclohexylmethylamine 
• 292638-85-8 acrylic acid methyl ester 
• 645386-71-6 1-(3,5-bis(trifluoromethyl)phenyl)butan-1-one 
• 401-95-6 3,5-Bis(trifluoromethyl)benzaldehyde 
• 1442660-26-5 (3,5-bis(trifluoromethyl)phenyl)(quinolin-8-yl)methanone 

Relevant articles and documents

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Exploring distal regions of the A3 adenosine receptor binding site: Sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands

We synthesized phenyl ring-substituted analogues of N6-(1S,2R)- (2-phenyl-1-cyclopropyl)adenosine, which is highly potent in binding to the human A3AR with a Ki value of 0.63nM. The effects of these structural changes on affinity at human and rat adenosine receptors and on intrinsic efficacy at the hA3AR were measured. A 3-nitrophenyl analogue was resolved chromatographically into pure diastereomers, which displayed 10-fold stereoselectivity in A3AR binding in favor of the 1S,2R isomer. A molecular model defined a hydrophobic region (Phe168) in the putative A3AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A3AR binding. Other related N6-substituted adenosine derivatives were included for comparison. Although the N 6-(2-phenyl-1-cyclopropyl) derivatives were full A3AR agonists, several other derivatives had greatly reduced efficacy. N 6-Cyclopropyladenosine was an A3AR antagonist, and adding either one or two phenyl rings at the 2-position of the cyclopropyl moiety restored efficacy. N6-(2,2-Diphenylethyl)adenosine was an A 3AR antagonist, and either adding a bond between the two phenyl rings (N6-9-fluorenylmethyl) or shortening the ethyl moiety (N 6-diphenylmethyl) restored efficacy. A QSAR study of the N 6 region provided a model that was complementary to the putative A3AR binding site in a rhodopsin-based homology model. Thus, a new series of high-affinity A3AR agonists and related nucleoside antagonists was explored through both empirical and theoretical approaches.