63591-85-5

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylacetyl)oxy]-
• CAS NO: 63591-85-5
• Molecular Formula: C16H11NO4
• Molecular Weight: 281.268
• Mol File: 63591-85-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylacetyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylacetyl)oxy]-(63591-85-5)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylacetyl)oxy]-(63591-85-5)

Safety Data

• Hazardous Substances Data: 63591-85-5(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 524-38-9 N-hydroxyphthalimide 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 87791-64-8 4(S)-methyl-3(S)-(phenylacetamido)-2-azetidinone 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 26087-47-8 iprobenfos 
• 13286-32-3 thiophosphoric acid S-benzyl ester O,O'-diethyl ester 

Relevant articles and documents

Decarboxylative Radical Addition to Methylideneoxazolidinones for Stereocontrolled Synthesis of Selectively Protected Diamino Diacids

Syntheses of stereochemically pure and selectively protected diamino diacids can be achieved by redox decarboxylation of distal N-hydroxyphthalimide esters of protected aspartic, glutamic or α-aminoadipic acids via radical addition to methylideneoxazolidinones. The products are useful for solid-supported syntheses of robust bioactive carbocyclic peptide analogs. Yields of reactive primary radical addition are superior to those of more stabilized radicals, and the reaction fails if the alkylideneoxazolidinone has a methyl substituent on its terminus (i.e., 13a/13b).

Photoinduced Decarboxylative Phosphorothiolation of N-Hydroxyphthalimide Esters

A visible-light-induced protocol for the synthesis of phosphorothioates is developed by employing the Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. This novel synthesis method utilizes carboxylic acids as raw material, which is stable, cheap, and commercially available. Scope studies show that this reaction has good compatibility of functional groups. Notably, both the synthesis of steric hindrance phosphorothioates and the later modification of some bioactive compounds are successfully achieved.

Chemoselective Union of Olefins, Organohalides, and Redox-Active Esters Enables Regioselective Alkene Dialkylation

Multicomponent catalytic processes that can generate multiple C(sp3)-C(sp3) bonds in a single step under mild conditions, particularly those that employ inexpensive catalysts and substrates, are highly sought-after in chemistry research for complex molecule synthesis. Here, we disclose an efficient Ni-catalyzed reductive protocol that chemoselectively merges alkenyl amides with two different aliphatic electrophiles. Starting materials are readily accessible from stable and abundant feedstock, and products are furnished in up to >98:2 regioisomeric ratios. The present strategy eliminates the use of sensitive organometallic reagents, tolerates a wide array of complex functionalities, and enables regiodivergent addition of two primary alkyl groups bearing similar electronic and steric attributes across aliphatic C=C bonds with exquisite control of site selectivity. Utility is underscored by the concise synthesis of bioactive compounds and postreaction functionalizations leading to structurally diverse scaffolds. DFT studies revealed that the regiochemical outcome originates from the orthogonal reactivity and chemoselectivity profiles of in situ generated organonickel species.