97424-48-1Relevant articles and documents
Porous Self-Assembled Molecular Networks as Templates for Chiral-Position-Controlled Chemical Functionalization of Graphitic Surfaces
Brown, Anton,Feyter, Steven De,Hashimoto, Shingo,Hirsch, Brandon E.,Ishikawa, Toru,Kaneko, Hiromasa,Kubo, Yuki,Tahara, Kazukuni,Tobe, Yoshito
, p. 7699 - 7708 (2020/08/19)
Controlled covalent functionalization of graphitic surfaces with molecular scale precision is crucial for tailored modulation of the chemical and physical properties of carbon materials. We herein present that porous self-assembled molecular networks (SAMNs) act as nanometer scale template for the covalent electrochemical functionalization of graphite using an aryldiazonium salt. Hexagonally aligned achiral grafted species with lateral periodicity of 2.3, 2.7, and 3.0 nm were achieved utilizing SAMNs having different pore-to-pore distances. The unit cell vectors of the grafted pattern match those of the SAMN. After the covalent grafting, the template SAMNs can be removed by simple washing with a common organic solvent. We briefly discuss the mechanism of the observed pattern transfer. The unit cell vectors of the grafted pattern align along nonsymmetry axes of graphite, leading to mirror image grafted domains, in accordance with the domain-specific chirality of the template. In the case in which a homochiral building block is used for SAMN formation, one of the 2D mirror image grafted patterns is canceled. This is the first example of a nearly crystalline one-sided or supratopic covalent chemical functionalization. In addition, the positional control imposed by the SAMN renders the functionalized surface (homo)chiral reaching a novel level of control for the functionalization of carbon surfaces, including surface-supported graphene.
Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
, p. 111 - 121 (2007/10/03)
Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
14C-Labeling of a novel prostacyclin I1 derivative, SM-10902
Kurosawa, Motohiro,Kanamaru, Hiroshi,Nishioka, Kazuhiko
, p. 129 - 138 (2007/10/03)
(+)-Methyl [2-[(2R,3aS,4R,5R,6aS)-octahydro-5-hydroxy-4-[(E)(3S,5S)-3-hydroxy-5-methyl-1 -[3-14C]nonenyl]-2-pentalenyl]ethoxy]-acetate ([nonenyl-3-14C]SM-10902) (1) was labeled with carbon-14 for use in mammalian metabolic studies. The synthesis was achieved in 7 steps from [14C]carbon dioxide: including: 1) Grignard reaction, 2) esterification, 3) condensation with dimethyl methylphosphonate, 4) Wittig-Horner reaction, 5) separation of isomers by HPLC. Stereoselective reduction of the protected ketone with sodium borohydride in the presence of cerium (III) chloride and subsequent desilylation produced 1. The overall yield was 11.1% from Ba[14C]CO3.
