139477-41-1

Basic information

• Product Name: 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl-
• Synonyms: 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl-;2,5-Pyrrolidinedione,3,4-Dihydroxy-1-(Phenylmethyl
• CAS NO: 139477-41-1
• Molecular Formula: C₁₆H₁₉NO₂
• Molecular Weight: 0
• Mol File: 139477-41-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 429.6°C at 760 mmHg
• Flash Point: 193.6°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 1.39E-07mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl-(139477-41-1)
• EPA Substance Registry System: 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl-(139477-41-1)

Safety Data

• Hazardous Substances Data: 139477-41-1(Hazardous Substances Data)

Usage

Appearance

White to off-white crystalline solid

Usage

Precursor in the synthesis of pharmaceuticals and other organic compounds

Medicinal properties

Potential anti-inflammatory and analgesic agent

Applications

Building block in the production of agrochemicals, dyes, and other specialty chemicals

Importance

Various fields of organic chemistry

Potential applications

Pharmaceutical and chemical industries

InChI:InChI=1/C16H19NO2/c18-15-11-14(12-7-3-1-4-8-12)16(19)17(15)13-9-5-2-6-10-13/h1,3-4,7-8,13-14H,2,5-6,9-11H2

Upstream product

• 635-51-8 2-phenylsuccinic acid 
• 108-91-8 cyclohexylamine 
• 1233241-12-7 C₁₇H₂₃NO₃ 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 16213-23-3 2-phenyl-N-cyclohexylmaleimide 
• 1631-25-0 N-cyclohexylmaleimide 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

Highly Enantioselective Synthesis of Chiral Succinimides via Rh/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation

We have successfully developed a highly enantioselective hydrogenation of various 3-aryl and 3-methyl maleinimides to access enantiomerically pure 3-substituted succinimides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos). This efficient catalytic system furnished the desired 3-substituted succinimide products with high yields and enantioselectivities (up to 99% yield, full conversions, almost all 3-aryl succinimide products up to 99% ee, and 3-methyl succinimide with 83% ee). Our catalytic system has a strong substrate tolerance and generality. Whether the N-substituted group of maleinimides is H or other protecting groups, the maleinimides were hydrogenated well (up to >99% ee, 99% yield). Moreover, the hydrogenation succinimide products can be readily utilized for the construction of biologically active molecules, such as chiral amides and pyrrolidines.

Low-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds was achieved at temperatures below 0 C using a Rh/MeO-F12-BIPHEP catalyst. The reaction of cyclohexenone or N-R-maleimide with arylboronic acids proceeded even at -80 C in the presence of the Rh catalyst. In the latter case, high enantioselectivity was observed because a low-temperature method was used, regardless of the type of substituent on maleimide.

Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues

Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogues in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF3-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biological interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization.