6343-01-7

Usage

Organic acid

Complex structure
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid is an organic acid, meaning it is primarily composed of carbon, hydrogen, and other elements such as oxygen and nitrogen. Its complex structure includes various functional groups that contribute to its properties and potential applications.

Functional groups

Phenyl and carboxylic acid
The presence of a phenyl group (a ring of six carbon atoms with a double bond between two of them) and a carboxylic acid functional group (a carboxyl group, -COOH, attached to a hydrogen atom) in the structure of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid contribute to its chemical properties and potential applications.

Rarity in nature

Not commonly found
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid is not commonly found in nature, which means it is likely a synthetic compound created through chemical reactions in a laboratory setting.

Synthesis

Laboratory settings
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid is often synthesized in laboratory settings for research purposes, as it is not commonly found in nature. The synthesis process may involve various chemical reactions and techniques to create the desired structure and properties.

Potential pharmacological properties

Suggested by chemical structure
The chemical structure of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid suggests that it may have potential pharmacological properties, making it of interest for pharmaceutical development.

Investigation and experimentation

Necessary for further understanding
To fully understand the properties, potential uses, and safety of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutanoic acid, further research and experimentation would be required. This may involve testing its chemical properties, stability, and potential interactions with other substances or biological systems.

Upstream product

• 85-44-9 phthalic anhydride 
• 1012-05-1 D,L-homophenylalanine 
• 103-63-9 1-phenyl-2-bromoethane 
• 200731-02-8 N-phthaloyl-L-(-)-4-oxo-homophenylalanine 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 943-73-7 D-homophenylalanine 
• 71-43-2 benzene 
• 16652-95-2 N²-phthalyl-L-aspartic anhydride 
• 5463-92-3 2-acetylamino-2-phenylethylmalonic acid diethyl ester 
• 100-39-0 benzyl bromide 
• 4443-40-7 phthaloylasparic anhydride 

Downstream Products

• 60504-99-6 2-Phthalimido-1-tetralon 
• 111210-75-4 (3,4-Dimethoxyphenyl)-(3-phenyl-1-phthalimidopropyl)-keton 
• 140408-88-4 N-phthaloylhomophenylalanine methyl ester 

Relevant academic research and scientific papers

General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization

α-Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H2O2 under mild conditions, provides access to modified α-amino acids via γ-C?H bond lactonization. The system can efficiently target 1°, 2° and 3° γ-C?H bonds of α-substituted and achiral α,α-disubstituted α-amino acids with outstanding site-selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well-established organometallic procedures.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected alpha-amino acids in NMR tubes, giving well distinguishable proton signals without interference which dramatically improve the accuracy of assignment and hasten the assigning procedure. The strategy is widely applicable for varied natural and non-natural amino acids.

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.

Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)-H Bonds

The transition-metal-catalyzed direct C-H bond fluorination is an attractive synthetic tool toward the preparation of organofluorines. While many methods exist for the direct sp3 C-H functionalization, site-selective fluorination of unactivated sp3 carbons remains a challenge. Direct, highly site-selective and diastereoselective fluorination of aliphatic amides via a palladium-catalyzed bidentate ligand-directed C-H bond functionalization process on unactivated sp3 carbons is reported. With this approach, a wide variety of β-fluorinated amino acid derivatives and aliphatic amides, important motifs in medicinal and agricultural chemistry, were prepared with palladium acetate as the catalyst and Selectfluor as the fluorine source.

Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors

Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR4═CR5—, —CR4═CR5—S—, —O—CR4═CR5—, —CR4═CR5—O—, —N═CR4—S—, —S—CR4═N—, —NR6—CR4═CR5— and —CR4═CR5—NR6—; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

The synthesis of L-(+)-homophenylalanine hydrochloride

L-(+)-Homophenylalanine hydrochloride was synthesized from N-phthaloyl-L-(-)-asparitc anhydride 2 in three steps in 55% overall yield with 99% ee. Copyright (C) 2000 Elsevier Science Ltd.

DESIGN AND SYNTHETIC APPLICATIONS OF NEW HETEROMETALLACYCLES

The reaction of cyclic anhydrides with Ni(0) complexes lead to the formation of nickelacycles by oxidative addition followed by decarbonylation.The preparation of chiral nickelacycles from anhydrides derived from amino acids and their reactivity is described.The formation of new heteropalladacycles by C-H activation or transmetallation reactions and their reactivity will be also discussed.

Synthesis of Cyclopropyl Amino Acid Derivatives

Derivatives of α,β-methanovaline, α,β-methanophenylalanine and β-methyl-α,β-methanoalanine have been prepared by regioselective side-chain functionalization of suitably protected amino acid derivatives, followed by cyclization with either sodium hydride or 1,8-diazabicycloundec-7-ene.The approach used in this work illustrates a method for the synthesis of cyclopropyl amino acid derivatives which is complementary to existing procedures.

Intramolecular Friedel-Crafts Acylation of N-Phthaloyl-Substituted Arylalanyl and Homophenylalanyl Chlorides

N-Phthaloyl-protected arylalanyl and homophenylalanyl chlorides 5 are acylated intramolecularly to 2-phthalimido-1-indanones 6 and -1-tetralone (6d) with AlCl3 (two-fold molar amounts) or catalytic amounts of FeCl3.The cycloacylation to the tetralone 6d with AlCl3 or FeCl3 proceeds without racemisation in very good yields, whereas the cycloacylation to the indanone 6a with FeCl3 gives rise to racemisation.Mixed anhydrides 11 of N-phthaloyl-α-amino acids and trifluoromethanesulfonate were prepared from the N-phthaloylamino acid chlorides and silver triflate.Acylation of arenes 12 with 11a as well as cycloaddition of (S)-O-methyl-N-phthaloyltyrosine triflate can be achieved without racemisation and without a catalyst.