638-37-9Relevant articles and documents
Epoxide-opening cascades triggered by a Nicholas reaction: Total synthesis of teurilene
Rodríguez-L?pez, Julio,Pinacho Cris?stomo, Fernando,Ortega, Nuria,L?pez-Rodríguez, Matías,Martín, Víctor S.,Martín, Tomás
, p. 3659 - 3662 (2013)
Natural inspiration: Based on the biosynthesis of squalene-derived polyethers, a total synthesis of teurilene is described. The carbocation formation in the Nicholas reaction serves to control the initiation of a polyepoxide ring-opening cascade. The three furan rings present in teurilene were obtained in excellent yield in one step. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl. Copyright
2:2 condensation products from the reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes with succinaldehyde and glutaraldehyde
Okawara, Tadashi,Okamoto, Yoshinari,Ehara, Shuji,Yamasaki, Tetsuo,Furukawa, Mitsuru
, p. 2487 - 2493 (1996)
The reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes (1) with succinaldehyde (2) and glutaraldehyde (9) in water gave the 2:2 condensation products (4 and 10).
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Sutter
, p. 59 (1932)
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Diastereoselective Synthesis of Cyclic Five-Membered trans,trans-Configured Nitrodiols by Double Henry Reaction of 1,4-Dialdehydes
Fr?hlich, Janine,Lehmkuhl, Kirstin,Fr?hlich, Roland,Wünsch, Bernhard
, p. 589 - 594 (2015)
Conformationally constrained perhydroquinoxalines 4 show high κ receptor affinity, selectivity over related receptors and full agonistic activity. Since the κ affinity can be correlated with the dihedral angle of the ethylenediamine pharmacophore (4a: 55°/71°), the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. The first step of the synthesis represents a double Henry reaction of 1,4-dialdehydes 8 and 10 with nitromethane, leading predominantly to the trans,trans-configured nitrodiols 9 and 11. X-ray crystal structure analyses of 9 and 11 led to dihedral angles O2N-C-C-OH of 73.4 and 88.3°, respectively, which reflect the calculated dihedral angles of the hypothesized final products 5a and 6a. Since κ receptor affinity can be correlated with the dihedral angle of ethylenediamine pharmacophores, the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. X-ray crystal structure analyses of the synthesized compounds 9 and 11 led to dihedral angles of 73.4 and 88.3°, respectively, reflecting the calculated dihedral angles of the hypothesized final products 5a and 6a.
Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12-Prostaglandin J3
Pel?s, Andrejs,Gandhamsetty, Narasimhulu,Smith, James R.,Mailhol, Damien,Silvi, Mattia,Watson, Andrew J. A.,Perez-Powell, Isabel,Prévost, Sébastien,Schützenmeister, Nina,Moore, Peter R.,Aggarwal, Varinder K.
, p. 9542 - 9545 (2018)
Re-investigation of the l-proline catalyzed double aldol cascade dimerization of succinaldehyde for the synthesis of a key bicyclic enal intermediate, pertinent in the field of stereoselective prostaglandin synthesis, is reported. The yield of this process has been more than doubled, from 14 % to a 29 % isolated yield on a multi-gram scale (32 % NMR yield), through conducting a detailed study of the reaction solvent, temperature, and concentration, as well as a catalyst screen. The synthetic utility of this enal intermediate has been further demonstrated through the total synthesis of Δ12-prostaglandin J3, a compound with known anti-leukemic properties.
Degradation of gaseous unsymmetrical dimethylhydrazine by vacuum ultraviolet coupled with MnO2
Huang, Yuanzheng,Jia, Ying,Shen, Keke,Hou, Ruomeng,Zhang, Yongyong,Hou, Li'an
supporting information, p. 1194 - 1202 (2021/02/06)
In this study, α-, β-, and δ-MnO2 were prepared by a uniform hydrothermal method and then coupled with vacuum ultraviolet (VUV) for the degradation of gaseous unsymmetrical dimethylhydrazine (UDMH). The performance in the removal of UDMH, by-product distribution and mechanism were systematically investigated. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption/desorption, Field Emission Scanning Electron Microscopy (FE-SEM), Raman, thermogravimetry (TG), Fourier-transform infrared (FT-IR), X-ray photoelectron spectroscopy (XPS) and electron paramagnetic resonance (EPR) to investigate the factors affecting the catalytic activity. The results showed that O2 and H2O were essential for the removal of UDMH. Photooxidation and ozone catalytic oxidation contribute to the removal and mineralization of UDMH. The integrated process considerably improved the removal and mineralization of UDMH by ozone catalytic oxidation. More reactive oxygen species were generated in the integrated process. The catalytic activity of the prepared catalysts follows the order: δ-MnO2 > α-MnO2 > β-MnO2. δ-MnO2 displayed the highest removal rate of 100% and a CO2 concentration of 42 ppmv. The good performance of δ-MnO2 was mainly attributed to the large number of surface oxygen vacancies.
The structure modification of seven-membered aza-brigded neonicotinoids in order to investigate their impact on honey bees
Cao, Xiaofeng,Chen, Xi,Chen, Yuce,Li, Zhong,Xu, Xiaoyong
, p. 835 - 844 (2021/05/29)
In order to explore the relationship between the structure and the toxicity to honey bees of seven-membered aza-bridged neonicotinoids, 16 novel seven-membered aza-bridged neonicotinoid analogues are synthesized by replacing the pyridine ring, and changing the substituents on the pyridine ring, the electron-withdrawing group NO2 and the imidazole ring of our previously developed aza-bridged neonicotinoid 1-[(6-chloropyridin-3-yl)methyl)]-10-(2,5-dimethylphenyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epiminoimidazo azepine (C-29). The insecticidal bioactivities against cowpea aphid (Aphis craccivora) and the bee toxicities of these compounds are tested. Some of the title compounds present good insecticidal activities against cowpea aphid. The results also show that some of the title compounds exhibit lower bee toxicity than that of C-29 and imidacloprid. This suggests that changing the substituents on the neonicotinoids can influence the toxicity toward honey bees of these analogues.