10122-95-9Relevant articles and documents
DMAP-[2.2]paracyclophane: Observation of an unusual C-C insertion
De Rycke, Nicolas,Marrot, Jerome,Couty, Francois,David, Olivier R. P.
, p. 1980 - 1984 (2011)
A novel family of nucleophilic catalysts derived from 4-(dimethylamino) pyridine (DMAP) is described. The aminopyridine moiety is attached to a [2.2]paracyclophane skeleton, giving a catalyst with intrinsic planar chirality. Their synthesis is described starting from aminoparacyclophane 5 in four steps. In the course of this preparation, an unprecedented rearrangement involving a C-C bond insertion was observed, leading to an unexpected quinolone-phenyl[2.2] cyclophane (8). The target catalyst 16 was obtained in enantiopure form by formation of diastereomers with a chiral secondary amine, allowing simple chromatographic separation. Preliminary catalytic studies were also performed. Copyright
5-Deazaflavinocyclophane as a Novel Flavoenzyme Model. Synthesis and Diastereoface-differentiating Reactions
Yanada, Reiko,Higashikawa, Makiko,Miwa, Yoshihisa,Taga, Toru,Yoneda, Fumio
, p. 1387 - 1390 (1992)
New 5-deazaflavinocyclophane with planar chirality, a novel flavoenzyme model, has been synthesized.This compound provides the first example for selective diastereoface-differentiation during its own reduction and oxidation.
The synthesis of enantiomerically pure [2.2]paracyclophane derivatives
Rowlands, Gareth J.
, p. 1527 - 1534 (2008)
[2.2]Paracyclophane is a fascinating molecule that offers great potential in a wide range of chemical disciplines. Currently, the synthesis of the majority of enantiomerically pure [2.2]paracyclophane derivatives is based on the resolution of a small numb
Diastereoselective Hartwig-Buchwald reaction of chiral amines with rac-[2.2]paracyclophane derivatives
Kreis, Michael,Friedmann, Christian J.,Braese, Stefan
, p. 7387 - 7394 (2005)
A Hartwig-Buchwald addition of a variety of chiral amines to rac-4-bromo-[2.2]paracyclophane and rac-trifluoromethanesulfonic acid (4-[2.2]paracyclophane) ester was performed with high diastereoselectivities. Kinetic racemic resolution of the starting materials was achieved, providing a rapid access to enantiomerically enriched 4-bromo-[2.2]paracyclophane and the corresponding enantiomerically pure [2.2]paracyclophane amines. Additionally, the first reaction of a secondary amine with a [2.2]paracyclophane halide was achieved.
Para-Functionalization of N-Substituted 4-amino[2.2]paracyclophanes by Regioselective Formylation
Felder, Simon,Micouin, Laurent,Benedetti, Erica
, p. 4015 - 4018 (2021/05/03)
Herein, we report a simple and convenient procedure to prepare para-disubstituted [2.2]paracyclophanes in a straightforward manner. Our approach relies on a regioselective formylation of N-substituted 4-amino[2.2]paracyclophanes, which allows an easy access to a series of products incorporating a reactive aldehyde function para to the electron-donating group. These compounds can be engaged in a variety of orthogonal late-stage derivatization processes involving either the carbonyl group or the amine function, and can serve as precursors to rapidly access more complex paracyclophane derivatives. Control of planar chirality is also possible by performing a kinetic resolution of key racemic intermediates through asymmetric transfer hydrogenation. The formylation can be run on a synthetically useful scale, thus confirming the practical applicability of our method.
A Parylene A precursor synthesis method (by machine translation)
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Paragraph 0027; 0035-0042; 0049-0068, (2018/10/19)
The invention discloses a Parylene A precursor synthesis method, comprises the following steps: (1) to [2, 2] - to di-methyl benzene ring b body as raw materials through the nitration reaction to obtain the intermediate product 4 - nitro - [2, 2] - dimethyl benzene ring to the second body; (2) the intermediate product 4 - nitro - [2, 2] - dimethyl benzene ring on the second body is arranged in the reactor into the hydrogen in the hydrogenation catalyst under the action of the reduction reaction, to get the crude product, concentrated, recrystallization, dried to obtain 4 - amino - [2, 2] - dimethyl benzene ring on the second body. The mild reaction conditions of the method, the resulting product yield and purity are relatively high, the catalyst and the solvent can be recycled, is suitable for mass production. (by machine translation)
