6306-54-3

Basic information

• Product Name: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (aS)-
• Synonyms: 2-Isoindolineaceticacid, a-isopropyl-1,3-dioxo-, L- (8CI);2H-Isoindole-2-acetic acid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (S)-;(S)-2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-methylbutanoic acid;L-N-Phthaloylvaline; N-Phthaloyl-(S)-valine; N-Phthaloyl-L-valine; NSC 22912
• CAS NO: 6306-54-3
• Molecular Formula: C₁₃H₁₃NO₄
• Molecular Weight: 247.2466
• Mol File: 6306-54-3.mol
• Article Data: 54

Chemical Properties

• Melting Point: 114-115 °C
• Boiling Point: 416.5°C at 760 mmHg
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 1.11E-07mmHg at 25°C
• Refractive Index: 1.597
• PKA: 3?+-.0.10(Predicted)
• CAS DataBase Reference: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (aS)-(6306-54-3)
• EPA Substance Registry System: 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (aS)-(6306-54-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• Hazardous Substances Data: 6306-54-3(Hazardous Substances Data)

Usage

General Description

2H-Isoindole-2-acetic acid, 1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-, (αS)-is a chemical compound with the molecular formula C12H13NO4. It is a chiral compound, with the (αS)-enantiomer being the active form. 2H-Isoindole-2-aceticacid, 1,3-dihydro-a-(1-methylethyl)-1,3-dioxo-, (aS)- is commonly used as a pharmaceutical intermediate in the synthesis of various drugs. It has been studied for its potential pharmacological properties, including anti-inflammatory and analgesic effects. The compound has also been investigated for its potential use in the treatment of central nervous system disorders.

InChI:InChI=1/C13H13NO4/c1-7(2)10(13(17)18)14-11(15)8-5-3-4-6-9(8)12(14)16/h3-7,10H,1-2H3,(H,17,18)/t10-/m0/s1

Upstream product

• 85-44-9 phthalic anhydride 
• 640-68-6 D-Val-OH 
• 1242459-41-1 C₁₉H₂₉NO₄Si₂ 
• 5115-65-1 N-phthaloyl-DL-valine 
• 72-18-4 L-valine 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 17498-50-9 L-valine hydrochloride 
• 438470-19-0 methyl 2-(N-succinimidyloxycarbonyl)benzoate 
• 4376-18-5 Monomethyl phthalate 
• 88-95-9 Phthaloyl dichloride 
• 17858-14-9 dimethyl (1-chloro-1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate 
• 516-06-3 D,L-valine 

Downstream Products

• 126875-70-5 Valin-N-(4-methylphenyl)hydroxamsaeure 
• 126901-04-0 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-hydroxy-3-methyl-N-p-tolyl-butyramide 
• 5699-54-7 (R)-3-amino-4-methylpentanoic acid 
• 20556-14-3 L-valyl-L-isoleucine 
• 3918-94-3 Val-Val 
• 777904-56-0 4-methyl-3-phthalimido-pentanoic acid 
• 72342-64-4 Methyl-β-phthalimido-γ-methylvalerat 
• 1094530-70-7 (S)-benzyl 4-(1,3-dioxoisoindolin-2-yl)-5-methyl-3-oxohexanoate 
• 908253-01-0 (S)-N¹-phenyl-3-methylbutane-1,2-diamine 
• 882528-81-6 Val-NH-iPr 
• 99529-85-8 C₁₉H₁₈N₂O₃ 
• 1309478-53-2 C₁₉H₁₇FN₂O₃ 
• 870533-29-2 (S)-2-amino-N-(4-fluorophenyl)-3-methylbutanamide 
• 1309478-56-5 C₁₁H₁₇FN₂ 

Relevant articles and documents

Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations

A unique decarbonylation of an amino acid derivative catalytic system has been established via palladium-catalyzed C-C bond and C-N bond dual activations. By employing 8-aminoquinoline as the directing group, this transformation has been found to facilitate the high chemoselectivity to decarbonylation of amino acid derivatives rather than intramolecular deamination or cross-dehydrogenative coupling reactions. This method provides a straightforward avenue for constructing diverse functionalized amide compounds in good to excellent yields. We proposed a possible reaction pathway that may go through the C-C bond and C-N bond dual activations on the basis of the mechanistic studies.

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.

Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide-DMAD Cycloadducts

Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides by a 2-carbonylphenyl moiety, are obtained.