61740-29-2

Upstream product

• 930-60-9 maleic anhydride 
• 61305-35-9 (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone 
• 61305-37-1 (S)-4-tetrahydropyranyloxy-2-cyclopenten-1-one 
• 61305-37-1 (S)-4-(Tetrahydro-pyran-2-yloxy)-cyclopent-2-enone 
• 56745-67-6 (4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one 
• 58616-75-4 (3S,4S)-3,4-O-Isopropylidene-L-threitolcyclopentanone dimethyldithioketal S-oxide 
• 63603-18-9 (+)-4(S)-hydroxy-2-cyclopenten-1(R)-yl N-mesyl-(S)-phenylalaninate 
• 14320-38-8 cyclopent-3-enol 
• 10493-98-8 2-hydroxy-2-cyclopenten-1-one 
• 74017-10-0 6-oxabicyclo<3.1.0>hexan-3-one 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 98-00-0 (2-furyl)methyl alcohol 
• 6573-26-8 cyclopentadiene endoperoxide 
• 765-56-0 4-bromocyclopent-2-enone 

Downstream Products

• 93292-92-3 (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester 
• 460990-23-2 (1R,3S)-1-(3-Trimethylsilanyl-prop-2-ynyl)-cyclopent-4-ene-1,3-diol 
• 85700-43-2 5E,7E-Clavulone II 
• 93292-93-4 [(1S,4S)-1,4-Bis-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl]-acetic acid tert-butyl ester 
• 3859-41-4 1,3-cyclopentadione 
• 59995-47-0 (R)-(+)-4-hydroxy-2-cyclopentenone 
• 59995-47-0 (-)-4-hydroxycyclo-2-pentenone 
• 59995-47-0 (+)-4-hydroxycyclo-2-pentenone 
• 768-48-9 4-acetoxy-cyclopentenone 
• 77341-51-6 (+/-)-4-benzoyloxy-2-cyclopentenone 
• 75988-65-7 4-oxocyclopent-2-enyl N-phenylcarbamate 
• 930-30-3 cyclopent-2-enone 
• 61305-35-9 (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone 
• 183612-91-1 (+/-)-4-benzyloxy-2-cyclopentenone 

Relevant academic research and scientific papers

An Enantioselective Approach to 4-O-Protected-2-cyclopentene-l,4-diol Derivatives via a Rhodium-Catalyzed Redox-Isomerization Reaction

Kinetic resolution of a series of cyclopentene-1,4-diol derivatives has been successfully achieved with enantiomeric excess up to 99.4% and a kf/ks ratio of 55 by a rhodium-catalyzed redox-isomerization reaction in a noncoordinating solvent.

Application of hierarchical pore molecular sieve in preparation process of cyclopentadiene and JP-10 aviation fuel

The invention relates to an application of a hierarchical pore molecular sieve in a the preparation process of cyclopentadiene and JP-10 aviation fuel. The hierarchical pore molecular sieve is one or two or more of an H-ZSM-5 molecular sieve, an H-beta molecular sieve, an H-Y molecular sieve, an H-USY molecular sieve, a La-Y molecular sieve and an H-MOR molecular sieve with a hierarchical pore structure, a sulfonated SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Ti-SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Zr-MCM-41 molecular sieve and a sulfonated Zr-SBA-15 molecular sieve; and the hierarchical pore structure comprises micropores and mesopores. The catalyst and the raw materials used in the method are cheap and easy to obtain, the preparation process is simple, and the hierarchical pore molecular sieve has high activity and selectivity for rearrangement reaction of furfuryl alcohol, hydrogenation reaction of hydroxyl cyclopentenone and dehydration reaction. The invention provides a cheap and efficient synthesis method for synthesizing the JP-10 aviation fuel from a lignocellulose-based platform compound furfuryl alcohol.

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

Bio-based synthesis of cyclopentane-1,3-diamine and its application in bifunctional monomers for poly-condensation

A novel and green route for the synthesis of cyclopentane-1,3-diamine (CPDA) from hemicellulosic feedstock is established in this work. Through many explorations and optimizations, the single successful multi-step synthesis was found to comprise: (1) the Piancatelli rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone (4-HCP), (2) a highly improved isomerization of4-HCPinto cyclopentane-1,3-dione (CPDO) using the Ru Shvo catalyst, (3) conversion ofCPDOinto cyclopentane-1,3-dioxime (CPDX), and (4) a mild oxime hydrogenation ofCPDXover Rh/C to afford the desiredCPDA. In addition, diastereomerically purecis- andtrans-isomers ofCPDAwere reacted with (A) bio-based lactones, and (B) 5-(hydroxymethyl)furfural (HMF) to synthesize novel bifunctional diol monomers with internal amide and imine groups, respectively. Monomer5, derived using γ-valerolactone (GVL), was successfully applied in the synthesis of polyurethanes.

Synthesis of agelastatin A and derivatives premised on a hidden symmetry element leading to analogs displaying anticancer activity

Concise total syntheses of (±)-7-hydroxy debromo agelastatin A (AglA), (±)-AglA, and 11-nitro AglA are presented based on an identified pseudo-symmetry element. This synthetic strategy was developed based on a desire to improve solubility of this potent anticancer agent while also developing a synthetic strategy that would enable late-stage variation of the pyrrole moiety. A stability study of pyrrole-derived carbinolamines revealed critical substituent effects impacting the equilibrium between the cyclic carbinolamine and keto pyrrole forms. 7-Hydroxy AglA existed primarily in the ketopyrrole form however the des-bromo variant existed primarily in the cyclic carbinolamine form. Cytotoxicity assays revealed activity for a 13-nitro AglA derivative (～14–63 μM) for breast cancer cells (MDA-MB-231 and MCF7) and a glioblastoma cell line (U87) while for 7-hydroxy des-bromo AglA, measurable activity was only observed against the glioblastoma cell line.

A gradient reduction strategy to produce defects-rich nano-twin Cu particles for targeting activation of carbon-carbon or carbon-oxygen in furfural conversion

Complexity of chemical linkages (C-C/C-H/C-O, C=C/C=O, or C-O-H/C-O-C) in biomass-derived molecules makes the selective activation of targeted bonds much more challenging, expecting well-defined catalysts and definite catalytically-active sites. This work demonstrates an effective gradient reduction strategy to control the definite structure of catalytically-active sites, affording defects-rich nano-twin Cu particles. This strategy just involves the reduction (calcination under H2) of CuII-containing layered double hydroxides (LDHs) simply with controlling the reduction gradient (interval time) of CuII species in two chemical micro-environments (CuII-O-CuII and CuII-O-MII/III/IV (M ≠ Cu)) in the brucite-like layer of LDHs. The nano-twin Cu particles efficiently promote the target activation of C-O and C=C in the conversion of furfural to cyclopentanone (CPO). With ~100% furfural conversion, the defects-rich nano-twin Cu particles afford a CPO selectivity of 92%, 50% higher than regular spherical Cu particles. The multi-stepped defect sites, originating from the planar defects, play a decisive role in promoting the CPO selectivity by facilitating the hydro-deoxygenation to C-O of 4-hydroxycyclopentenone (HCP) and hydrogenation to C=C of HCP or cyclopentenone.

Double-metal cyanide as an acid and hydrogenation catalyst for the highly selective ring-rearrangement of biomass-derived furfuryl alcohol to cyclopentenone compounds

Herein, novel green synthetic routes to 4-hydroxy-2-cyclopentenone (HCP) and 2-cyclopentenone (CPE) from biomass-derived furfuryl alcohol via double-metal cyanide catalysis are proposed. For the synthesis of HCP, in comparison to conventional solid acids (i.e., Amberlyst-15), MOFs with coordinatively unsaturated metal ions as pure Lewis acid sites exhibit advantageous catalytic selectivity in the reaction under an N2 atmosphere in a bi-phasic water/n-hexane solvent system. FeZn and FeZn-P result in an HCP yield of 77.4% and 88.2%, respectively. For the CPE synthesis, the reaction conditions are the same as those for HCP, except a mono-phasic water solvent system and H2 atmosphere were employed. In addition to the acid-catalyzed rearrangement reaction, FeZn-DMC exhibits catalytic hydrogenation capability via heterolytic cleavage of the H-H bond over Zn-N frustrated Lewis pairs, and a CPE yield of 61.5% is obtained. The DFT simulation indicates that the acid sites and catalytic acid sites are ascribed to the tri-coordinatively unsaturated Zn2+ site (Zn(N)3) on the catalyst surface. Moreover, the DMC catalyst shows excellent stability and recycling performance. This work not only provides an efficient and green catalytic system for CPE and HCP preparation but also demonstrates the interesting bifunctional catalysis of both acid and hydrogenation catalysis over DMC.

Method for cyclization conversion of furfuryl alcohol to form cyclopentenone

The invention discloses a method for cyclization conversion of furfuryl alcohol to form cyclopentenone. The method comprises the following steps: mixing furfuryl alcohol with a solvent mixture according to a mass ratio of 1:(20-60) g/ml, and adding Lewis solid acid as a catalyst to carry out a reaction in an inert gas or hydrogen environment, wherein the reaction temperature is 120-160 DEG C. Through adoption of the technical scheme, 4-hydroxy-2-cyclopentenone/2-cyclopentenone is obtained by adopting a rearranging hydrolysis/hydrogenolysis method, so that the process is simple, operation is convenient, reaction conditions are mild, and the catalyst is cheap and easily available and can be recycled for multiple times. The method is easy to industrialize, excessive dependence on petroleum isreduced by the raw materials, and the environmental problems of halogen pollution are reduced. When the conversion rate of furfuryl alcohol for synthesizing 4-hydroxy-2-cyclopentenone reaches 95.2%,the yield is up to 88.2%; and when the conversion rate of furfuryl alcohol for synthesizing 2-cyclopentenone is up to 96%, the yield is up to 52.3%.

Concise Syntheses of ?"12-Prostaglandin J Natural Products via Stereoretentive Metathesis

δ12-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four δ12-prostaglandin J natural products (7-8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.

TOTAL SYNTHESIS OF PROSTAGLANDIN J NATURAL PRODUCTS BY STEREORETENTIVE METATHESIS

This invention relates generally to the synthesis of Δ12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ12- Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).