57677-67-5

Basic information

• Product Name: 1(3H)-Isobenzofuranone, 4-phenyl-
• CAS NO: 57677-67-5
• Molecular Formula: C14H10O2
• Molecular Weight: 210.232
• Mol File: 57677-67-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1(3H)-Isobenzofuranone, 4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(3H)-Isobenzofuranone, 4-phenyl-(57677-67-5)
• EPA Substance Registry System: 1(3H)-Isobenzofuranone, 4-phenyl-(57677-67-5)

Safety Data

• Hazardous Substances Data: 57677-67-5(Hazardous Substances Data)

Upstream product

• 412300-27-7 2'-formyl-biphenyl-2,3'-dicarboxylic acid 
• 192884-95-0 4-Phenyl-4,7-dihydro-3H-isobenzofuran-1-one 
• 96600-65-6 (3aS,4R)-4-Phenyl-3a,4-dihydro-3H-isobenzofuran-1-one 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 98369-32-5 6-Oxo-6H-pyran-2-carboxylic acid (E)-3-phenyl-allyl ester 

Downstream Products

• 86-73-7 9H-fluorene 

Relevant articles and documents

Rhodium(II)-catalyzed carbocyclization reaction of α-diazo carbonyls with tethered unsaturation

o-Alkynyl-substituted α-diazoketones undergo internal cyclization to produce indenone derivatives upon treatment with catalytic quantities of Rh(II)-carboxylates. A variety of structural influences were encountered by varying the nature of the substituent group attached to the diazo center. The cyclization reaction involves addition of a rhodium-stabilized carbenoid onto the acetylenic π-bond to generate a cycloalkenone carbenoid. The cyclized carbenoid was found to undergo both aromatic and aliphatic C-H insertion as well as cyclopropanation across a tethered π-bond. Subjection of diazo phenyl acetic acid 3-phenylprop-2-ynyl ester to Rh(II) catalysis furnished 8- phenyl-1,8-dihydro2-oxacyclopenta[a]indenone in high yield. The formation of this compound involves cyclization of the initially formed carbenoid onto the alkyne to produce a butenolide which then undergoes C-H insertion into the neighboring aromatic system. When a vinyl ether is added, the initially formed rhodium carbenoid intermediate can be intercepted by the electron-rich π-bond prior to cyclization. Different rhodium catalysts were shown to result in significant variation in the product ratios. The competition between bimolecular cyclopropanation, 1,2-hydrogen migration, and internal cyclization was probed using several enol ethers as well as diazoesters which possess different substituent groups on the ester backbone. The specific path followed was found to depend on electronic, steric, and conformational factors.

REACTION OF 3a,4-DIHYDROPHTHALIDES WITH ACETYLENIC DIENOPHILES

The tricycloocta-2,5-diene-4,7-carbolactones, the initially-formed Diels-Alder adducts from 3a,4-dihydrophthalides and acetylenic dienophiles, were so strained that they underwent the retro-Diels-Alder reaction to afford the benzene derivatives in good yields.