PROPANEDIOIC ACID, 2-(2-NITRO-1-PHENYLETHYL)-, 1,3-DIETHYL ESTER

Base Information

• Chemical Name: PROPANEDIOIC ACID, 2-(2-NITRO-1-PHENYLETHYL)-, 1,3-DIETHYL ESTER
• CAS No.: 22975-21-9
• Molecular Formula: C15H19NO6
• Molecular Weight: 309.3145
• Mol file: 22975-21-9.mol

Synonyms:HMS2601M15;diethyl 2-(2-nitro-1-phenylethyl)malonate;CL 520;

Chemical Property of PROPANEDIOIC ACID, 2-(2-NITRO-1-PHENYLETHYL)-, 1,3-DIETHYL ESTER

Chemical Property:

• Vapor Pressure: 1.12E-07mmHg at 25°C
• Boiling Point: 432.3°Cat760mmHg
• Flash Point: 171.8°C
• PSA: 98.42000
• Density: 1.195g/cm³
• LogP: 2.31250

Purity/Quality:

99% ^*data from raw suppliers

DIETHYL 2-(2-NITRO-1-PHENYLETHYL)MALONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PROPANEDIOIC ACID, 2-(2-NITRO-1-PHENYLETHYL)-, 1,3-DIETHYL ESTER

There total 32 articles about PROPANEDIOIC ACID, 2-(2-NITRO-1-PHENYLETHYL)-, 1,3-DIETHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

nitrostyrene (5153-67-3) + diethyl malonate (105-53-3) → diethyl 2-(3-nitrophenylethyl)malonate (71639-13-9,22975-21-9)

Guidance literature:

With lithium phenolate; (S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.12.003

Reference yield: 99.0%

(2-nitroethenyl)benzene (102-96-5) + diethyl malonate (105-53-3) → (R)-1,3-diethyl 2-(2-nitro-1-phenylethyl)malonate (22975-21-9)

Guidance literature:

With poly((1S,2S)-N¹,N²-bis(4-hydrooxybenzyl)cyclohexane-1,2-diamine naphthalene-2,7-disulfate (diester)), complex with NiBr₂; In dichloromethane; at 20 ℃; for 24h; Solvent; enantioselective reaction; Catalytic behavior;

DOI:10.1016/j.tetlet.2020.152792

Reference yield: 99.0%

(2-nitroethenyl)benzene (102-96-5) + diethyl malonate (105-53-3) → ethyl (S)-2-ethoxycarbonyl-4-nitro-3-phenylbutyrate (252338-27-5,22975-21-9)

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)benzyl)-3-((1S,2S)-2-(dimethylamino)cyclohexyl)thiourea; In toluene; at 20 ℃; enantioselective reaction;

DOI:10.1002/anie.201601028

upstream raw materials:

nitrostyrene

sodium diethylmalonate

(2-nitroethenyl)benzene

diethyl malonate

Downstream raw materials:

(3R,4S)-ethyl 4-(phenyl)-2-oxopyrrolidine-3-carboxylate

4-phenylpyrrolidin-2-one

4-amino-3-phenylbutanoic acid

2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide

Refernces

• 1、 Terada, Masahiro,Ube, Hitoshi,Yaguchi, Yusuke. "Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes". . p. 1454 - 1455. Retrieved 2006.
• 2、 Selvi, Subramani,Srinivasan, Kannupal. "Tandem Ring Opening/Cyclization of trans-2-Aryl-3-nitrocyclopropane-1,1-dicarboxylates with 2-Aminopyridines: Access to Pyrido[1,2-a]pyrimidin-4-one Derivatives". . p. 5644 - 5648. Retrieved 2017.
• 3、 Reznikov,Klimochkin. "Reaction of ω-nitrostyrene with diethyl malonate in the presence of chiral nickel(II) complexes". . . Retrieved 2012.
• 4、 Bittorf, Lukas,Held, Christoph,Knierbein, Michael,Reiser, Oliver,Sadowski, Gabriele,Siewert, Riko,Verevkin, Sergey P.,Weinbender, Thomas. "High-Pressure-Mediated Thiourea-Organocatalyzed Asymmetric Michael Addition to (Hetero)aromatic Nitroolefins: Prediction of Reaction Parameters by PCP-SAFT Modelling". . p. 1292 - 1296. Retrieved 2020.
• 5、 Reznikov,Golovin,Klimochkin. "Enantioselective addition of diethyl malonate to ω-nitrostyrenes in the presence of cobalt and manganese complexes with N,N′-dibenzyl-(1S,2S)- cyclohexane-1,2-diamine". . . Retrieved 2012.
• 6、 Wang, Peipei,Li, Wanjiao,Han, Kehui,Guo, Yanchun,Zhao, Yufen,Cao, Shuxia. "Application of pentacoordinated spirophosphorane as a new organocatalyst for the Michael addition reaction". . p. 936 - 947. Retrieved 2021.
• 7、 Ye, Jinxing,Dixon, Darren J.,Hynes, Peter S.. "Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives". . p. 4481 - 4483. Retrieved 2005.
• 8、 Mukherjee, Tathagata,Ganzmann, Carola,Bhuvanesh, Nattamai,Gladysz, John A.. "Syntheses of enantiopure bifunctional 2-guanidinobenzimidazole cyclopentadienyl ruthenium complexes: Highly enantioselective organometallic hydrogen bond donor catalysts for carbon-carbon bond forming reactions". . p. 6723 - 6737. Retrieved 2014.
• 9、 Dib, Mohammed El Amine,El Ouar, Ibtissem,Keniche, Assia,Zeghina, Ibtissem. "Synthesis and Biological Analysis of Anti-addiction Effect and Hepatotoxicity of Tow Baclofen Analogues Complexed with β-Cyclodextrin". . p. 187 - 196. Retrieved 2022/02/02.
• 10、 Sato, Kazuki,Umeno, Tomohiro,Ueda, Atsushi,Kato, Takuma,Doi, Mitsunobu,Tanaka, Masakazu. "Asymmetric 1,4-Addition Reactions Catalyzed by N-Terminal Thiourea-Modified Helical l-Leu Peptide with Cyclic Amino Acids". supporting information. p. 11216 - 11220. Retrieved 2021/06/21.