81699-66-3

Basic information

• Product Name: Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate
• Synonyms: Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate
• CAS NO: 81699-66-3
• Molecular Weight: 204.269
• Mol File: 81699-66-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate(81699-66-3)
• EPA Substance Registry System: Ethyl 1-methyl-2-phenylcyclopropane-1-carboxylate(81699-66-3)

Safety Data

• Hazardous Substances Data: 81699-66-3(Hazardous Substances Data)

Upstream product

• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 74-88-4 methyl iodide 
• 623-73-4 diazoacetic acid ethyl ester 
• 766-90-5 cis-1-phenyl-1-propylene 
• 873-66-5 1-propenylbenzene 
• 81699-64-1 2,2-Dimethyl-3-phenyl-3-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 
• 100-42-5 styrene 
• 10606-64-1 3-methyl-5-phenyl-tetrahydrofuran-2-one 
• 10606-65-2 Aethyl 4-chloro-2-methyl-4-phenyl-butanoat 

Relevant articles and documents

Highly diastereoselective and enantioselective olefin cyclopropanation using engineered myoglobin-based catalysts

Using rational design, an engineered myoglobinbased catalyst capable of catalyzing the cyclopropanation of aryl-substituted olefins with catalytic proficiency (up to 46800 turnovers) and excellent diastereo- and enantioselectivity (98-99.9%) was developed. This transformation could be carried out in the presence of up to 20 gL-1 olefin substrate with no loss in diastereo- and/or enantioselectivity. Mutagenesis and mechanistic studies support a cyclopropanation mechanism mediated by an electrophilic, heme-bound carbene species and a model is provided to rationalize the stereopreference of the protein catalyst. This work shows that myoglobin constitutes a promising and robust scaffold for the development of biocatalysts with carbene-transfer reactivity.

Chiral C2-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination

A new series of chiral C2-symmetric bisferrocenyldiimine 1 and bisferrocenyldiamines 2 and 3 proved to be efficient ligands for the copper(I)-catalyzed asymmetric cyclopropanation, cyclopropenation, and aziridination of alkenes and alkynes to give high diastereo- and enantioselectivity as well as high chemical yields. In some instances the enantiomeric excesses of cyclopropanated products are among the highest (>97% ee) ever reported. Comparative studies show that stereoselectivity depends highly on the steric variation both in the ligand and the substrate. Other transition metal complexes incorporating some of these ligands such as Ru(3c)Cl2, [(NBD)Rh(2)]ClO4, [Cu(2)(MeCN)2]PF6, and Pd(2)Cl2 also demonstrated high enantioselectivity in cyclopropanation reactions.

AN INTERPRETATION OF THE SUBSTITUENT EFFECT IN THE BLAISE REARRANGEMENT IN TERMS OF PI-ORBITALS

The migratory aptitude of the substituent groups in the Blaise rearrangement can be explained in terms of the pi-electronic properties of the groups in the highest occupied molecular orbitals.The rates of the rearrangement reaction with relation to the substituent groups were also rationally understood based on the energy levels of the molecular orbitals.