Dimethyl 3-cyclopentene-1,1-dicarboxylate

Base Information

• Chemical Name: Dimethyl 3-cyclopentene-1,1-dicarboxylate
• CAS No.: 84646-68-4
• Molecular Formula: C9H12O4
• Molecular Weight: 184.192
• Hs Code.: 2917209090
• DSSTox Substance ID: DTXSID90351391
• Nikkaji Number: J1.677.334D
• Wikidata: Q72469711
• Mol file: 84646-68-4.mol

Synonyms:84646-68-4;Dimethyl 3-cyclopentene-1,1-dicarboxylate;dimethyl cyclopent-3-ene-1,1-dicarboxylate;Methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate;3-Cyclopentene-1,1-dicarboxylic acid dimethyl ester;Enamine_000260;SCHEMBL7090808;DTXSID90351391;PQMIUYZOJQILOZ-UHFFFAOYSA-N;HMS1394L18;BCP24344;MFCD00154460;AKOS001038189;AS-15542;Dimethyl-3-cyclopentene-1,1-dicarboxylate;dimethylcyclopent-3-ene-1,1-dicarboxylate;CS-0061802;FT-0625058;W16710;A852725;Z56766443;3-CYCLOPENTENE-1,1-DICARBOXYLICACIDDIMETHYLESTER

Chemical Property of Dimethyl 3-cyclopentene-1,1-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.255mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 205.1 °C at 760 mmHg
• Flash Point: 91.5 °C
• PSA: 52.60000
• Density: 1.183g/cm³
• LogP: 0.66880
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

98%min ^*data from raw suppliers

Dimethyl3-Cyclopentene-1,1-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC=CC1)C(=O)OC

Technology Process of Dimethyl 3-cyclopentene-1,1-dicarboxylate

There total 20 articles about Dimethyl 3-cyclopentene-1,1-dicarboxylate 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%

diallyl malonate (1797-75-7) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (84646-68-4)

Guidance literature:

With C₈₉H₈₉Cl₂N₄ORu; In n-heptane; at 100 ℃; for 2.33333h; Reagent/catalyst; Inert atmosphere;

Reference yield: 99.0%

Z-1,4-dichlorobutene (1476-11-5) + malonic acid dimethyl ester (108-59-8) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (84646-68-4)

Guidance literature:

malonic acid dimethyl ester; With lithium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

Z-1,4-dichlorobutene; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2008.11.065

Reference yield: 99.0%

diallylmalonic acid diethyl ester (3195-24-2) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (84646-68-4)

Guidance literature:

With C₃₄H₃₆BrCl₂N₄ORu; In toluene; at 80 ℃; for 1.5h; Temperature; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.jorganchem.2017.04.003

upstream raw materials:

diazomethane

Cyclopent-3-ene-1,1-dicarboxylic acid bis-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Z-1,4-dichlorobutene

malonic acid dimethyl ester

Downstream raw materials:

methyl cyclopent-3-ene-1-carboxylate

benzyl {2-[4-(3-chloropropoxy)phenyl]-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl}carbamate

benzyl (2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl)carbamate

Refernces

• 1、 Gupta, Saswata,Sabbasani, Venkata R.,Su, Siyuan,Wink, Donald J.,Lee, Daesung. "Alkene-chelated ruthenium alkylidenes: A missing link to new catalysts". . p. 1977 - 1987. Retrieved 2021.
• 2、 Amori, Laura,Costantino, Gabriele,Marinozzi, Maura,Pellicciari, Roberto,Gasparini, Fabrizio,Flor, Peter J.,Kuhn, Rainer,Vranesic, Ivo. "Synthesis, molecular modeling and preliminary biological evaluation of 1-amino-3-phosphono-3-cyclopentene-1-carboxylic acid and 1-amino-3-phosphono-2-cyclopentene-1-carboxylic acid, two novel agonists of metabotropic glutamate receptors of group III". . p. 1447 - 1450. Retrieved 2000.
• 3、 Batuecas, Maria,Esteruelas, Miguel A.,Garcia-Yebra, Cristina,Gonzalez-Rodriguez, Carlos,Onate, Enrique,Saa, Carlos. "Ruthenium hydroxycarbenes as key intermediates in cycloisomerization and decarbonylative cyclization of terminal alkynals". . p. 3474 - 3480. Retrieved 2014.
• 4、 Gupta, Saswata,Su, Siyuan,Zhang, Yu,Liu, Peng,Wink, Donald J.,Lee, Daesung. "Ruthenabenzene: A Robust Precatalyst". supporting information. p. 7490 - 7500. Retrieved 2021/05/26.
• 5、 Tanaka, Masakazu,Yakabi, Haruka,Nakatani, Haruki,Ueda, Atsushi,Doi, Mitsunobu,Oba, Makoto. "Helical structures of cyclopentenebased α,α-disubstituted a-amino acid homopeptides". . p. 848 - 852. Retrieved 2019/01/21.