88466-67-5

Usage

Type of compound

Synthetic organic compound

Uses

Anticonvulsant and sedative-hypnotic drug

Mechanism of action

Suppresses the central nervous system

Treatment applications

Epilepsy and other neurological disorders

Physical form

Crystalline solid

Color

White to off-white

Melting point

172-175°C

Precautions

Toxic if ingested or inhaled, causes skin and eye irritation

Upstream product

• 15851-87-3 5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 2033-24-1 cycl-isopropylidene malonate 
• 104-88-1 4-chlorobenzaldehyde 
• 479-27-6 naphthalene-1,8-diamine 

Downstream Products

• 88466-72-2 2-(4-Chloro-benzyl)-3-oxo-3-piperidin-1-yl-propionic acid methyl ester 
• 88466-70-0 dimethyl 2-(4-chlorobenzyl)malonate 
• 88466-69-7 1-tert-butyl 3-methyl 2-(4-chlorobenzyl)malonate 
• 130296-65-0 5,5'-Bis-(4-chloro-benzyl)-2,2,2',2'-tetramethyl-[5,5']bi[[1,3]dioxanyl]-4,6,4',6'-tetraone 
• 1167473-07-5 2-(4-chlorobenzyl)malonic acid benzyl ester methyl ester 

Relevant academic research and scientific papers

Asymmetric Synthesis of α-Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis

The first asymmetric α-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N-O bond cleavage provided access to undescribed α-trifluoromethylthio-β2,2-amino acids, with promising applications in biochemistry and medicinal chemistry.

Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids

Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated

Synthesis of 2-aryl-1H-benzimidazoles and 2-aryl-1H-perimidines using arylidene Meldrum’s acid as a source of the aryl group and oxidant

Arylidene Meldrum’s acid is employed as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H–benzimidazoles by a condensation reaction with 1,2-phenylenediamine in refluxing ethanol with good to high yields. Arylidene Meldrum’s acids were

Quaternary β2,2-Amino Acids: Catalytic Asymmetric Synthesis and Incorporation into Peptides by Fmoc-Based Solid-Phase Peptide Synthesis

β-Amino acid incorporation has emerged as a promising approach to enhance the stability of parent peptides and to improve their biological activity. Owing to the lack of reliable access to β2,2-amino acids in a setting suitable for peptide synthesis, most contemporary research efforts focus on the use of β3- and certain β2,3-amino acids. Herein, we report the catalytic asymmetric synthesis of β2,2-amino acids and their incorporation into peptides by Fmoc-based solid-phase peptide synthesis (Fmoc-SPPS). A quaternary carbon center was constructed by the palladium-catalyzed decarboxylative allylation of 4-substituted isoxazolidin-5-ones. The N?O bond in the products not only acts as a traceless protecting group for β-amino acids but also undergoes amide formation with α-ketoacids derived from Fmoc-protected α-amino acids, thus providing expeditious access to α-β2,2-dipeptides ready for Fmoc-SPPS.

Synthesis and characterization of tricarbastannatranes and their reactivity in B(C6F5)3-promoted conjugate additions

The synthesis and characterization of a series of tricarbastannatranes, in the solid state and in solution, are described. The structures of the complexes [N(CH2CH2CH2)3Sn](BF4), [N(CH2CHs

METHYLENE LINKED QUINOLINYL MODULATORS OF RORyt

The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction

A general process for the high-yielding synthesis of substituted chiral and achiral α-substituted acrylates was achieved through the sequential one-pot combination of a metal-free reductive coupling reaction followed by an Eschenmoser methylenation. The proline catalyzed reaction of Meldrum's acid, aldehydes and Hantzsch ester followed by methylenation was successful with Eschenmoser's salt in the presence of an alcohol solvent. Herein, we have shown the high-yielding synthesis of privileged building blocks from chiral/achiral α-substituted acrylates and shown them to be very good intermediates in the pharmaceuticals and natural products synthesis. This journal is the Partner Organisations 2014.

Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: Diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals

In this paper we describe new multi-catalysis cascade (MCC) reactions for the one-pot synthesis of highly functionalized non-symmetrical malonates. These metal-free reactions are either five-step (olefination/hydrogenation/alkylation/ ketenization/esterif

A novel and green protocol for two-carbon homologation: A direct amino acid/K2CO3-catalyzed four-component reaction of aldehydes, active methylenes, Hantzsch esters and alkyl halides

A novel and green approach for the two-carbon homologation of aldehydes using amino acid catalysis has been developed and further extended to the generation of pharmaceutically active cyano-esters via four-component reactions in one-pot.

One Pot Synthesis of Monoalkylated and Mixed, Dialkylated Meldrum's Acid Derivatives

A simple one pot method, involving sequential Knoevenagel condensation of Meldrum's acid with aromatic aldehydes, conjugate reduction of ylidene Meldrum's acid using sodium borohydride followed by alkylation, to prepare mixed dialkylated derivatives of Meldrum's acid is described.