1590-22-3Relevant articles and documents
Phenanthrylalkanoic acids I: Syntheses of Biological Activities of 1-Phenanthryl Derivatives
Eirin,Fernandez,Gomez,Lopez,Santos,Calleja,De La Iglesia,Cano
, p. 1110 - 1118 (1987)
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Chemistry of unique chiral olefins. 1. Synthesis, enantioresolution, circular dichroism, and theoretical determination of the absolute stereochemistry of trans- and cis-1,1',2,2',3,3',4,4'-Octahydro-4,4'- biphenanthrylidenes
Harada, Nobuyuki,Saito, Akira,Koumura, Nagatoshi,Uda, Hisashi,De Lange, Ben,Jager, Wolter F.,Wynberg, Hans,Feringa, Ben L.
, p. 7241 - 7248 (1997)
Unique chiral olefins, (E)-1,1',2,2',3,3',4,4'-octahydro-4,4'-biphenanthrylidene (1) and its (Z)-isomer 2, were synthesized. When these compounds are directly enantioresolved by using the HPLC Okamoto column with a chiral stationary phase, optically pure enantiomers were obtained. The CD spectra of these chiral olefins exhibit very intense Cotton effects in the 1B(b) transition region reflecting their strongly twisted π-electron systems. The CD and UV spectra of chiral olefins (M,M)-E-1 and (M,M)-(Z)-2 were theoretically calculated by the π-electron self-consistent field/configuration interaction/dipole velocity molecular orbital method. From the calculation results, the absolute stereostructures of these chiral olefins were theoretically determined to be [CD(+)239.0]-(M,M)-(E)-1 and [CD(+)238.1]-(M,M)-(Z)-2, respectively.
Iron(II) and zinc(II) monohelical binaphthyl salen complexes
Wiznycia, Alexander V.,Desper, John,Levy, Christopher J.
, p. 4693 - 4695 (2005)
A new chiral binaphthyl salen ligand with rigid polyaromatic sidearms gives monohelical Complexes (FeII and ZnII) of predetermined handedness. The Royal Society of Chemistry 2005.
Synthesis, characterization and structural aspects of new haptens for PAHs
Li, Yi,Yang, Mingming,Liu, Yuanyuan,Wei, Rongqing,Liu, Xiaoning,Li, Fangshi
, p. 206 - 213 (2011)
Two new haptens for PAHs, 4-(naphthalen-2-yl)-4-oxobutanoic acid (I) and 4-(anthracen-1-yl)-4-oxobutanoic acid (II), were synthesized and confirmed by elemental analysis, IR, and 1H NMR. Single crystal X-ray structure showed that compound I crystallizes in the triclinic crystal system (space group = P-1). A classic hydrogen bonded dimer is formed by the carboxylic acid group from two molecules. The R22 (8) graph-set motif links the molecules into pairs around inversion centers in the unit cell. The O-H?O hydrogen-bonded interactions involving these pairs are very strong and stabilize molecular packing of these dimers into a unique assembly. Compound II crystallizes in the Monoclinic crystal system (space group = P21/c). Similarly to compound I, a classic hydrogen bonded dimer is formed by the carboxylic acid group from two molecules. The R22 (8) graph-set motif links the molecules into pairs around inversion centers in the unit cell. Besides, an intramolecular hydrogen bonding causes the formation of a planar six-membered ring, which is also coplanar with the adjacent anthracene ring. The geometries of the corresponding parts of the haptens are almost the same as those of naphthalene and anthracene. Ab initio Hartree-Fock computational calculation provided the supports that the size, shape (geometry) and electronic properties at the corresponding parts of the haptens did not change significantly, compared to those of naphthalene and anthracene. The haptens were coupled with bovine serum albumin (BSA) to make antigents. The coupling ratio of I-BSA was 1:20, and II-BSA 1:37, respectively. These results showed that the new haptens could be used to induce specific antibodies for PAHs.
Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters
Shi, Yongjie,Tan, Xuefeng,Gao, Shuang,Zhang, Yao,Wang, Jingxin,Zhang, Xumu,Yin, Qin
supporting information, p. 2707 - 2713 (2020/03/30)
Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.
Efficient Hydrogenation of Biomass Oxoacids to Lactones by Using NHC–Iridium Coordination Polymers as Solid Molecular Catalysts
Liu, Yaoqi,Sun, Zheming,Huang, Changyu,Tu, Tao
, p. 355 - 360 (2017/02/05)
A series of NHC–iridium coordination polymers have proven to be robust, efficient and recyclable solid molecular catalysts toward the hydrogenation of biomass levulinic acid (LA) to γ-valerolactone. Along with quantitative yields attained at 0.01 mol % catalyst loading under 50 atm of H2, the solid molecular catalyst was readily recovered and reused for 12 runs without obvious loss of the selectivity and activity. Remarkably, up to 1.2×105 TON, an unprecedented value could be achieved in this important transformation. In addition, a number of LA homologues, analogues and derivatives were well tolerated to deliver various intriguing and functional lactones in good to excellent yields, which further confirmed the feasibility of the solid molecular catalysts.
