137386-99-3

Basic information

• Product Name: (1R*,2R*)-N-methoxy-N-methyl-2-phenylcyclopropanecarboxamide
• CAS NO: 137386-99-3
• Molecular Weight: 205.257
• Mol File: 137386-99-3.mol

Chemical Properties

• CAS DataBase Reference: (1R*,2R*)-N-methoxy-N-methyl-2-phenylcyclopropanecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1R*,2R*)-N-methoxy-N-methyl-2-phenylcyclopropanecarboxamide(137386-99-3)
• EPA Substance Registry System: (1R*,2R*)-N-methoxy-N-methyl-2-phenylcyclopropanecarboxamide(137386-99-3)

Safety Data

• Hazardous Substances Data: 137386-99-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 100-52-7 benzaldehyde 
• 217318-54-2 2-diazo-N-methoxy-N-methyl-acetamide 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 4192-77-2 ethyl cinnamate 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 939-87-7 (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride 

Downstream Products

• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 

Relevant articles and documents

One-pot approach for the synthesis of trans-cyclopropyl compounds from aldehydes. Application to the synthesis of GPR40 receptor agonists

A novel multicatalytic one-pot process providing trans-cyclopropyl compounds from corresponding aldehydes has been developed and applied to the synthesis of GPR40 small molecule agonists. The Royal Society of Chemistry.

SERINE/THREONINE PAK1 INHIBITORS

Compounds having the formula I wherein A, Z, R1a, R1b, R2, R3, R4, R5, R6, R7, R9, R10, Ra, Rb and n are as defined herein are inhibitors of PAK1. Also disclosed are compositions and methods for treating cancer and hyperproliferative disorders.

Hypersensitive mechanistic probe studies of cytochrome P450-catalyzed hydroxylation reactions. Implications for the cationic pathway

Details of the mechanism of cytochrome P450-catalyzed hydroxylation reactions were investigated by oxidation of trans-2-phenyl-1- alkylcyclopropanes (alkyl = methyl (1), ethyl (2), 1-propyl (3), 1- methylethyl (4)) and trans-2-(4-(trifluoromethyl)phenyl)-1-alkylcyclopropanes (alkyl = methyl (5), ethyl (6)). The syntheses of 3 and 6 and their possible oxidation products are reported. Oxidation of the probes with the cytochrome P450 isozyme CYP2B1 gave unrearranged cyclopropylcarbinols as major products and small amounts of ring-opened alcohol products in all cases except for 4. Phenolic products also were produced from substrates 1-4. The maximum lifetimes of putative radical intermediates were less than 1 ps, and the results with substrate 4 require that no intermediate was formed. The results were analyzed in the context of recent mechanistic proposals for cytochrome P450-catalyzed hydroxylations. Oxidation of a 'radical' component in the transition state of an insertion reaction to produce a cation is inconsistent with the results. The results also provide little support for a new alternative mechanism for hydroxylation, the agostic complex model (Collman, J.P.; Chien, A. S.; Eberspacher, T. A.; Brauman, J. I. J. Am. Chem. Soc. 1998, 120, 425). Formation of 'cationic' rearrangement products via solvolysis of first-formed protonated alcohol products produced by insertion of the 'OH+' moiety from iron-complexed hydrogen peroxide also is not supported by the results. The most consistent mechanistic description is the recently reported multistate reactivity paradigm (Shaik, S.; Filatov, M.; Schroder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193).