84646-68-4

Basic information

• Product Name: Dimethyl 3-Cyclopentene-1,1-dicarboxylate
• Synonyms: DIMETHYL 3-CYCLOPENTENE-1,1-DICARBONATE;DIMETHYL 3-CYCLOPENTENE-1,1-DICARBOXYLATE;dimethyl 3-cyclopentene dicarbonate;3-CYCLOPENTENE-1,1-DICARBOXYLIC ACID DIMETHYL ESTER;DiMethyl cyclopent-3-ene-1,1-dicarboxylate;Methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate
• CAS NO: 84646-68-4
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19
• Mol File: 84646-68-4.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 205.1 °C at 760 mmHg
• Flash Point: 91.5 °C
• Appearance: /
• Density: 1.183g/cm³
• Vapor Pressure: 0.255mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Dimethyl 3-Cyclopentene-1,1-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 3-Cyclopentene-1,1-dicarboxylate(84646-68-4)
• EPA Substance Registry System: Dimethyl 3-Cyclopentene-1,1-dicarboxylate(84646-68-4)

Safety Data

• Hazardous Substances Data: 84646-68-4(Hazardous Substances Data)

Usage

General Description

Dimethyl 3-Cyclopentene-1,1-dicarboxylate is a chemical compound with the molecular formula C10H14O4. It is a colorless, clear liquid that is used in organic synthesis and as a reagent in the production of pharmaceuticals, fragrances, and other chemical compounds. It is known for its versatility and its ability to participate in a variety of chemical reactions, making it a valuable tool for researchers and manufacturers in the chemical industry. Dimethyl 3-Cyclopentene-1,1-dicarboxylate is typically handled and stored in a controlled environment due to its flammable and potentially hazardous nature, and proper safety precautions should always be taken when working with it.

InChI:InChI=1/C9H12O4/c1-12-7(10)9(8(11)13-2)5-3-4-6-9/h3-4H,5-6H2,1-2H3

Upstream product

• 1476-11-5 Z-1,4-dichlorobutene 
• 108-59-8 malonic acid dimethyl ester 
• 205320-79-2 trans-4,4-dicarbomethoxy-1,7-octadiene 
• 35357-77-8 dimethyl bisallylmalonate 
• 764-41-0 1,4-dichloro-2-butene 
• 591-87-7 Allyl acetate 
• 40637-56-7 dimethyl allylmalonate 
• 115580-32-0 (Z)-but-2-ene-1,4-diyl di-tert-butyl dicarbonate 
• 1797-75-7 diallyl malonate 
• 3195-24-2 diallylmalonic acid diethyl ester 
• 352664-56-3 dimethyl 2-(2-oxoethyl)-2-(prop-2-yn-1-yl)malonate 
• 821-06-7 (E)-1,4-dibromobutene 
• 186581-53-3 diazomethane 
• 84658-43-5 Cyclopent-3-ene-1,1-dicarboxylic acid bis-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 

Downstream Products

• 58101-60-3 methyl cyclopent-3-ene-1-carboxylate 
• 7686-77-3 3-cyclopentene-1-carboxylic acid 
• 76909-91-6 rel-(1R,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol 
• 76910-02-6 3-cyclopenten-1,1-dimethanol 
• 1004764-72-0 benzyl {2-[4-(3-chloropropoxy)phenyl]-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl}carbamate 
• 1004764-73-1 benzyl (2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl)carbamate 
• 1381843-11-3 dimethyl 4-(3-(trifluoromethyl)phenyl)cyclopent-2-ene-1,1-dicarboxylate 

Relevant articles and documents

Rate enhancement by ethylene in the ru-catalyzed ring-closing metathesis of enynes: Evidence for an "ene-then-yne" pathway that diverts through a second catalytic cycle

(Chemical Equation Presented) Mixing it: A dual-substrate/dual isotopic labeling strategy has shown that the accelerating effect of ethylene in intermolecular ring-closing metathesis of enynes is best explained by an ene-then-yne mechanism rather than the

Lipase-catalyzed kinetic resolution of cyclic trans-1,2-diols bearing a diester moiety: Synthetic application to chiral seven-membered-ring α,α-disubstituted α-amino acid

(Chemical Equation Presented) Chiral cycloalkane-trans-1,2-diols (±)-3 and (±)-8 having a diester moiety have been prepared from dimethyl dialkenylmalonate using olefin metathesis by Grubbs catalyst, followed by epoxidation and acidic hydrolysis. Kinetic

A simple oxidative procedure for the removal of ruthenium residues from metathesis reaction products

Ruthenium residues can be easily and rapidly removed from Grubbs metathesis products by washing with 15% aqueous hydrogen peroxide, which converts any ruthenium complexes into highly insoluble ruthenium dioxide, which then catalyzes the conversion of excess peroxide into water and oxygen. Ruthenium levels lower than 2 ppm can be routinely obtained; an additional advantage is that any phosphines are also rapidly oxidized to the corresponding, more polar phosphine oxides thereby facilitating their removal as well in many cases.

Generation and spectroscopic characterization of ruthenacyclobutane and ruthenium olefin carbene intermediates relevant to ring closing metathesis catalysis

The reaction of phosphonium alkylidenes [(H2IMes)RuCl 2=CHPR3]+[A]- (R = C 6H11, A = OTf or B(C6F5) 4, 1-Cy; R = i-C3H7, A = CIB(C 6F5)3 or OTf, 1-iPr) with 1 equiv of ethylene at -78°C, in the presence of 2-3 equiv of a trapping olefin substrate, yields intermediates relevant to olefin metathesis catalytic cycles. Dimethyl cyclopent-3-ene-1,1-dicarboxylate gives solutions of a substituted ruthenacy-clobutane 3 of relevance to ring closing metathesis catalysis. 1H and 13C NMR data are fully consistent with its assignment as a ruthenacyclobutane, but 1JCC values of 23 Hz for the CαH2-Cβ bond and 8.5 Hz for the CαH-Cβ bond point to an unsymmetrical structure in which the latter bond is more activated than the former. In contrast, trapping with acenaphthylene leads to an olefin carbene complex (6) in which the putative ruthenacyclobutane has opened; this species was also fully characterized by NMR spectroscopy and compared to related species reported previously.

NHC (N-heterocyclic carbene) ligand, ruthenium catalyst thereof, preparation methods and application

The invention relates to an NHC (N-heterocyclic carbene) ligand, a ruthenium catalyst thereof, preparation methods and an application of the catalyst. The NHC ligand structures are shown in formulas Ia and Ib respectively, and the corresponding ruthenium catalyst structures are shown in formulas IIa and IIb respectively. After large steric hindrance and electron-rich groups are simultaneously introduced to the NHC ligand structures, the catalytic activity and the stability of the ruthenium complex catalyst of the NHC ligand are notably improved, and the application range of the ruthenium complex catalyst of the NHC ligand is notably enlarged.

Development of a One-Pot Four C-C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis

A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).