27946-19-6

Usage

InChI:InChI=1/C15H14ClNO/c16-14(13-9-5-2-6-10-13)15(18)17-11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,18)/t14-/m1/s1

Upstream product

• 2912-62-1 α-chlorophenylacetyl chloride 
• 100-46-9 benzylamine 
• 33326-49-7 N-benzyl-N-hydroxy-2-phenylacetamide 
• 142437-79-4 N-(mesyloxy)-N-benzylphenylacetamide 
• 188025-29-8 Methanesulfonic acid benzylcarbamoyl-phenyl-methyl ester 
• 81384-43-2 2-(benzylamino)-2-oxo-1-phenylethyl acetate 
• 780-25-6 N-benzylidene benzylamine 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 27845-50-7 (E)-N-benzylidenebenzylamine 
• 112776-40-6 1-Benzyl-2,2-dichloro-3-phenyl-aziridine 
• 103-80-0 phenylacetyl chloride 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 

Downstream Products

• 6109-33-7 4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 705283-47-2 N-benzyl-2-dimethylamino-2-phenyl-acetamide 

Relevant academic research and scientific papers

2,7-Diazabicyclo[2.2.1]heptanes: Novel asymmetric access and controlled bridge-opening

Organocatalysed asymmetric Michael additions of substituted triketopiperazines to enones afford products in high yield and enantiomeric ratio (er). Further modification delivers products possessing natural product (NP) scaffolds including diazabicyclo[2.2

A new chemoenzymatic approach to the synthesis of chiral 4-aryl-1,4-dihydro-2H-isoquinolines via the enzymatic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3-one

A new chemoenzymatic method is proposed for the synthesis of enantiomerically pure 4-phenyl-1,4-dihydro-2H-isoquinolines based on the enzymatic kinetic resolution of 2-acetyl-4-phenyl-1,4-dihydro-2H-isoquinolin-3- one. For the enzymatic resolution of the racemic substrate, readily available 'home made' animal liver acetone powders (LAPs) were used. Excellent enantioselectivity, exceeding 500, was achieved in a short reaction time upon application of turkey liver acetone powder as the biocatalyst. Reduction of obtained product led to the formation of amine (R)-1, which is hardly available using standard procedures. These results show that N-acetyl lactams are a new type of substrate for enzymatic biotransformations.

Novel synthesis of gem-dichloroaziridines from imines via the KF/Al 2O3-promoted generation of dichlorocarbene from chloroform

KF/Al2O3 was found to be an efficient base for the reaction of imines with chloroform in acetonitrile to give gem- dichloroaziridines 2 in moderate to high yields. The KF/ Al2O 3-promoted dichloroaziridination c

N-Substituted amino acid N′-benzylamides: Synthesis, anticonvulsant, and metabolic activities

Amino acid amides (AAA) were prepared and evaluated in seizure models. The AAA displayed moderate-to-excellent activity in the maximal electroshock seizure (MES) test and were devoid of activity in the subcutaneous Metrazol-induced (scMet) seizure test. The AAA anticonvulsant activity was neither strongly influenced by the C(2) substituent nor by the degree of terminal amine substitution. An in vitro metabolism study suggested that the structure-activity relationship pattern was due, in part, to metabolic processes that occurred at the N-terminal amine unit.

The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent

Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenylacetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/g. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED50 value for the former in the MES test was 3.0 mg/kg (ip), which compared favorably with phenobarbital (ED50=22 mg/kg), but the ED50 value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg.

Base-Promoted Reaction of O-Sulfonylated Hydroxamic Acids with Nucleophiles. A New Mehtod for the Synthesis of α-Substituted Amides

Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0 deg C gives 2-chloroamides 3 in good yields.Use of a single equivalent of triethylamine gives the N-(mesyloxy)amides 1, which are versatile sy

A Convenient Synthetic Route to 4-Aryl-1,4-dihydro-3(2H)-isoquinolinones

The title compounds are synthesized by Friedel-Crafts cyclization of N-benzyl-α-chloroacetamides, derived from the dichlorocarbene adducts of benzaldehyde N-benzylimines.