271246-25-4

Basic information

• Product Name: ethyl 2-methylallyl 2-diazo-2-phenylacetate
• Synonyms: ethyl 2-methylallyl 2-diazo-2-phenylacetate
• CAS NO: 271246-25-4
• Molecular Weight: 216.239
• Mol File: 271246-25-4.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2-methylallyl 2-diazo-2-phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-methylallyl 2-diazo-2-phenylacetate(271246-25-4)
• EPA Substance Registry System: ethyl 2-methylallyl 2-diazo-2-phenylacetate(271246-25-4)

Safety Data

• Hazardous Substances Data: 271246-25-4(Hazardous Substances Data)

Upstream product

• 103-80-0 phenylacetyl chloride 
• 128863-93-4 2-methyl-2-propen-1-yl phenylacetate 

Downstream Products

• 333956-68-6 (1R,5S)-5-methyl-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 57496-93-2 5-methyl-1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one 
• 345350-13-2 (1R,2S)-1-phenyl-2-methyl-2-(azidomethyl)-N,N-diethylcyclopropanecarboxamide 

Relevant articles and documents

Dirhodium(II) tetrakis[methyl 2-oxaazetidine-4-carboxylate]: A chiral dirhodium(II) carboxamidate of exceptional reactivity and selectivity

A new chiral azetidinone-carboxylate ligand for dirhodium(II) catalysts enhances reactivity toward diazo decomposition and selectivity toward cyclopropanation enabling diazomalonates, vinyldiazoacetates, and aryldiazoacetates to be effectively used with a dirhodium(II) carboxamidate catalyst.

Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates

A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.

Oxime Ether Synthesis through O-H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation

A green and sustainable oxime ether formation method via the visible-light-promoted O-H functionalization of oximes with diazo esters is described. The reaction occurs under very mild conditions (catalyst- and additive-free) with a high yield and a high functional group tolerance. When the reaction was performed with a cyclic ether as the solvent (e.g., THF, 1,4-dioxane, tetrahydropyran, ect.), an interesting photochemical three-component reaction product was obtained in good yields.

Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives

A visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates is developed. This one-pot two step reaction offers a mild and efficient approach for the synthesis of biologically important 2,3-dihydrobenzofuran derivatives in good yields and moderate diastereoselectivities.

Catalyst-free, visible-light-promoted S-H insertion reaction between thiols and α-diazoesters

A visible-light-promoted S-H insertion reaction between thiols and α-diazoesters was developed. The reaction proceeded smoothly at room temperature with a broad substrate scope, affording various thioethers in moderate to excellent yields. The catalyst- A

Toward a Large-Scale Approach to Milnacipran Analogues Using Diazo Compounds in Flow Chemistry

The safe use of diazo reagents for the preparation of a key structure in the synthesis of milnacipran analogues is described herein. Using continuous flow technology, the diazo reagent is synthesized, purified, dried, and subsequently used in semi-batch mode for an intramolecular cyclopropanation. Side products formed in the reaction are isolated and rationalized to optimize the process. Different separation techniques in flow are compared with regard to their ability to produce pure and dry diazo reagents. The studies yield a scalable process to a key intermediate in the syntheses of milnacipran and its possible substituted analogues.

Enantioselective iron-catalyzed intramolecular cyclopropanation reactions

An iron-catalyzed asymmetric intramolecular cyclopropanation was realized in high yields and excellent enantioselectivity (up to 97% ee) by using the iron complexes of chiral spiro-bisoxazoline ligands as catalysts. The superiority of iron catalysts exhibited in this reaction demonstrated the potential abilities of this sustainable metal in asymmetric carbenoid transformation reactions.

A New Enantioselective Synthesis of Milnacipran and an Analogue by Catalytic Asymmetric Cyclopropanation

Milnacipran and analogues are conveniently prepared by a short sequence of steps from phenylacetic acid, the key step being highly enantio-selective catalytic asymmetric cyclopropanation.