165657-63-6

Basic information

• Product Name: (+)-N-BENZYL-D-MALIMIDE
• Synonyms: (R)-2-HYDROXY-N-BENZYLSUCCINIMIDE;(R)-1-BENZYL-3-HYDROXYPYRROLE-2,5-DIONE;(+)-N-BENZYL-D-MALIMIDE;(R)-1-Benzyl-3-hydroxypyrrolidine-2,5-dione
• CAS NO: 165657-63-6
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 165657-63-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-N-BENZYL-D-MALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N-BENZYL-D-MALIMIDE(165657-63-6)
• EPA Substance Registry System: (+)-N-BENZYL-D-MALIMIDE(165657-63-6)

Safety Data

• Hazardous Substances Data: 165657-63-6(Hazardous Substances Data)

Usage

Description

(+)-N-BENZYL-D-MALIMIDE, also known as (3R)-3-Hydroxy-1-(phenylmethyl)-2,5-pyrrolidinedione, is a chemical compound that serves as an intermediate in the synthesis of various compounds. It is characterized by its unique structure and properties, making it a valuable component in chemical reactions and research.

Uses

Used in Pharmaceutical Synthesis:
(+)-N-BENZYL-D-MALIMIDE is used as an intermediate in the synthesis of Monocrotaline-d4 (M526002), a labelled version of the toxic pyrrolizidine alkaloid Monocrotaline (M526000). This alkaloid is isolated from Crotalaria spp. and is utilized for inducing pulmonary diseases in rats, contributing to the study and understanding of such conditions.
Used in Chemical Research:
As a chemical intermediate, (+)-N-BENZYL-D-MALIMIDE plays a crucial role in the development and synthesis of new compounds for various applications. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable tool for researchers in the field of chemistry and related disciplines.

Upstream product

• 636-61-3 D-Malic acid 
• 100-46-9 benzylamine 
• 156150-59-3 (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione 
• 165388-00-1 methyl (2R,3R)-4-(N-benzylcarbamoyl)-2,3-dihydroxybutyrate 
• 115061-63-7 (2R,3R)-2,3-diacetoxy-4-(benzylamino)-4-oxobutanoic acid 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 173353-28-1 3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione 
• 173353-27-0 1-benzyl-3-dodecanoyloxy-2,5-pyrrolidinedione 
• 173353-26-9 1-benzyl-3-hexanoyloxy-2,5-pyrrolidinedione 
• 173353-25-8 1-benzyl-3-isobutyryloxy-2,5-pyrrolidinedione 
• 173353-24-7 1-benzyl-3-propionyloxy-2,5-pyrrolidinedione 
• 129823-21-8 3-acetoxy-1-benzyl-2,5-pyrrolidinedione 

Downstream Products

• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 116143-02-3 (3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate 
• 156150-59-3 (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione 
• 202743-03-1 (3R)-1-benzyl-3-benzyloxy pyrrolidine-2,5-dione 

Relevant articles and documents

Substitutive nicotinamide compound, medicine composition and application of composition

The invention provides a substitutive nicotinamide compound, a composition containing the compound and application of the composition. The substitutive nicotinamide compound is shown in the formula (I) or pharmaceutically acceptable salt, prodrug, hydrate

FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

Lipase-catalyzed practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its related compounds

A practical method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (1) was investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepacia gave the best result: In a mixed solvent (1:1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis. The chain length of the alkanoyl does not noticeably influence the reaction rate or the enantioselectivity. In contrast, the hydrolysis of the 1-benzoyl derivative proceeded slowly with a low enantioselectivity (E = 19). The syntheses of optically active 3-hydroxypyrrolidines and 3-hydroxypiperidines were also achieved under the reaction conditions similar to the lipase PS-catalyzed hydrolysis of 2a.