101386-28-1

Basic information

• Product Name: 2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-a-2-propenyl-
• CAS NO: 101386-28-1
• Molecular Formula: C13H11NO4
• Molecular Weight: 245.235
• Mol File: 101386-28-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-a-2-propenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-a-2-propenyl-(101386-28-1)
• EPA Substance Registry System: 2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-a-2-propenyl-(101386-28-1)

Safety Data

• Hazardous Substances Data: 101386-28-1(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 1069-48-3 rac-allylglycine 

Downstream Products

• 691875-73-7 C₃₄H₂₉F₆N₃O₃ 

Relevant articles and documents

A Novel Class of 7-Membered Heterocyclic Compounds

The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully retained.

Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination

A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.

4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1′H-spiro[indene-1,4′-piperidin]-1′-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3′R)-3′-methyl-1′H-spiro[indene-1,4′-piperidin]-1′-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation.