295328-85-7

Basic information

• Product Name: (2S,5S)-2,5-DIPHENYLPYRROLIDINE
• Synonyms: (2S,5S)-2,5-DIPHENYLPYRROLIDINE;(S,S)-2,5-Diphenylpyrrolidine;Pyrrolidine,2,5-diphenyl-, (2S,5S)-;(2S,5S)-2,5-Diphenylpyrrolidine,99%e.e.
• CAS NO: 295328-85-7
• Molecular Formula: C₁₆H₁₇N
• Molecular Weight: 223.31
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 295328-85-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.048g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -112 ° (C=1, CHCl3)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.76±0.10(Predicted)
• CAS DataBase Reference: (2S,5S)-2,5-DIPHENYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2,5-DIPHENYLPYRROLIDINE(295328-85-7)
• EPA Substance Registry System: (2S,5S)-2,5-DIPHENYLPYRROLIDINE(295328-85-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 295328-85-7(Hazardous Substances Data)

Usage

General Description

(2S,5S)-2,5-Diphenylpyrrolidine is a chemical compound with the molecular formula C19H19N. It is a chiral compound consisting of a five-membered ring containing a nitrogen atom and two phenyl groups. (2S,5S)-2,5-DIPHENYLPYRROLIDINE is used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It is also utilized as a ligand in asymmetric catalysis and in the preparation of chiral auxiliaries for organic synthesis. Its chiral nature makes it an important reagent in the production of enantiomerically pure compounds. Additionally, its rigid structure makes it a useful tool in the study of molecular conformations and stereochemistry.

InChI:InChI=1/C16H17N/c1-3-7-13(8-4-1)15-11-12-16(17-15)14-9-5-2-6-10-14/h1-10,15-17H,11-12H2/t15-,16-/m0/s1

Upstream product

• 295328-86-8 (2S,5S)-N-allyl-2,5-diphenylpyrrolidine 
• 495-71-6 phenacylacetophenone 
• 214280-56-5 (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol 
• 295328-90-4 (1R,4R)-1,4-bis(methanesulfonyloxy)-1,4-diphenylbutane 
• 70-11-1 α-bromoacetophenone 
• 1376191-10-4 C₃₃H₃₉N 
• 1376191-15-9 C₁₆H₁₅N 
• 1569095-70-0 (2E)-N-methoxy-N-((1S)-1-phenylprop-2-en-1-yl)but-2-enamide 
• 1569095-79-9 (5S)-1-methoxy-5-phenylpyrrolidin-2-one 
• 100-58-3 phenylmagnesium bromide 
• 1569095-73-3 C₁₁H₁₁NO₂ 

Downstream Products

• 919087-08-4 (E)-1-((2S,5S)-2,5-Diphenyl-pyrrolidin-1-yl)-3-phenyl-propenone 
• 875275-34-6 ((4R,5R)-3,4-Diphenyl-4,5-dihydro-isoxazol-5-yl)-((2S,5S)-2,5-diphenyl-pyrrolidin-1-yl)-methanone 
• 1072809-78-9 (S,Z)-N,N-[(1S,4S)-1,4-diphenyl-1,4-butylidene]-5-phenyl-3-hexenamide 
• 1072809-60-9 (R,Z)-N,N-[(1S,4S)-1,4-diphenyl-1,4-butylidene]-5-phenyl-3-hexenamide 
• 1072809-81-4 (2R)-N,N-[(1'S,4'S)-1',4'-diphenyl-1',4'-butylidene]-2-[(benzyloxy)methyl]octanamide 
• 1355611-48-1 (S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-diphenylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate 
• 1355611-49-2 (S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-diphenylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate 
• 1355611-22-1 C₂₆H₂₆N₂O₂S 
• 1355611-46-9 C₃₂H₃₄N₂O₄S 
• 1355611-47-0 C₃₀H₃₂N₂O₂S 
• 1355611-19-6 C₂₆H₂₆N₂O₃ 
• 1376191-10-4 C₃₃H₃₉N 
• 35657-63-7 trans-N-Methyl-2,5-diphenylpyrrolidin 
• 444667-33-8 (2S,5S,11aR)-1-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2,5-diphenylpyrrolidine 

Relevant articles and documents

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

Addition of organometallic reagents to chiral N-methoxylactams: Enantioselective syntheses of pyrrolidines and piperidines

Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compou

Mukaiyama-Michael reactions with acrolein and methacrolein: A catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins

Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.