5515-64-0Relevant academic research and scientific papers
Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts
Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.
supporting information, p. 10102 - 10112 (2021/08/03)
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.
Phenol and dihydroxybenzene hydrogenation catalysts based on polyamide dendrimers and rhodium species
Zakharyan,Ma, Gouqiung,Maksimov,Karakhanov,Voronina
, p. 412 - 419 (2015/02/19)
Heterogeneous catalysts based on rhodium nanoparticles and first- and second-generation poly(amidoamine) (PAMAM) dendrimers crosslinked with hexamethylene diisocyanate have been synthesized. It has been found that catalyst samples with a particle size of 0.88 to 1.96 nm, depending on the PAMAM dendrimer generation, are effective in the hydrogenation of phenol, hydroquinone, resorcinol, and pyrocatechol (85°C, 30 atm O2, 2 h). In phenol hydrogenation, the selectivity for cyclohexanone is 100%. Cyclohexanone has not undergone further transformation under the reaction conditions. The main products of dihydroxybenzene hydrogenation have been trans-cyclohexanediols, with their proportion decreasing in the order: resorcinol > hydroquinone > pyrocatechol. The selectivity has been found to be 100% for 1,3-cyclohexanediol, 97-99% for 1,4-cyclohexanediol, and 33-91% for 1,2-cyclohexanediol. The catalysts based on the second-generation dendrimer have shown a high activity in dihydroxybenzene hydrogenation (TOF of 6600 to 35000 h-1).
Catalytic 1,3-difunctionalisation of organic backbones through a highly stereoselective, one-pot, boron conjugate-addition/reduction/oxidation process
Sole, Cristina,Tatla, Amolak,Mata, Jose A.,Whiting, Andrew,Gulyas, Henrik,Fernandez, Elena
supporting information; experimental part, p. 14248 - 14257 (2012/01/19)
A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imin
Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions
Maegawa, Tomohiro,Akashi, Akira,Yaguchi, Kiichiro,Iwasaki, Yohei,Shigetsura, Masahiro,Monguchi, Yasunari,Sajiki, Hironao
experimental part, p. 6953 - 6963 (2010/02/28)
An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.
Enzymatic resolution, desymmetrization, and dynamic kinetic asymmetric transformation of 1,3-cycloalkanediols
Fransson, Ann-Britt L.,Xu, Yongmei,Leijondahl, Karin,Baeckvall, Jan-E.
, p. 6309 - 6316 (2007/10/03)
An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S,3R)-3-(acetoxy)-1-cyclohexanol ((R,S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's
Pathways of liquid-phase oxidation of cyclohexanol
Puchkov,Buneeva,Perkel'
, p. 248 - 253 (2007/10/03)
The kinetics of product accumulation in uncatalyzed oxidation of cyclohexanol at 403 K was studied. Along with the compounds originating from oxidation of cyclohexanol at position 1 (cyclohexanone, hydrogen peroxide, 1-hydroxycyclohexyl hydroperoxide), products formed by oxidation of C-H bonds at positions 2-4 were detected: 2-, 3-, and 4-hydroxycyclohexyl hydroperoxides (cis and trans isomers), 1,2-, 1,3-, and 1,4-dihydroxycyclohexanes (cis and trans isomers), 2- and 4-hydroxycyclohexanones, and 2-cyclohexenone.
Molecular Recognition and Stereoselectivity: Geometrical Requirements for the Multiple Hydrogen-Bonding Interaction of Diols with a Multidentate Polyhydroxy Macrocycle
Kikuchi, Yasuaki,Kato, Yasushi,Tanaka, Yasutaka,Toi, Hiroo,Aoyama, Yasuhiro
, p. 1349 - 1354 (2007/10/02)
Resorcinol-dodecanal cyclotetramer 1 in CDCl3 forms hydrogen-bonded, 1/1 complexes with cyclohexanediols as well as with 2,4-pentane- and 2,5-hexanediol as their open-chain analogues and cyclohexanol and cis- and trans-4-tert-butylcyclohexanol.The affinities to 1 of cyclic diols (K=(1.1-10) * 102 M-1 at 25 deg C) are significantly larger than those of open-chain diols (36-43 M-1) and monools (8-11 M-1).Those of regio- and stereoisomers of cyclohexanediol depend on the configuration (axial-equatorial > diequatorial) and relative positions (1,4 >> 1,2 > 1,3) of the two OH groups involved and decrease in the order cis-1,4 (K=1.04 * 103) > cis-1,2 (2.64 * 102) > trans-1,3 (1.81 * 102) > trans-1,4 (1.29 * 102) > cis-1,3 (1.24 * 102) > trans-1,2 (1.06 * 102 M-1); the stereoselectivities are thus cis-1,4/trans-1,4 = 8.0, cis-1,2/trans-1,2 = 2.5, and trans-1,3/cis-1,3 = 1.5.The selectivities in the diol binding are discussed in terms of multiple hydrogen bonding of diol and 1.The relatively large binding constant (K) for cis-1,4-diol with one axial and one equatorial OH group is attributed to an effective and simultaneous two-point hydrogen bonding of the two OH groups with two adjacent binding sites of 1 as a multidentate host.
