70719-19-6Relevant articles and documents
Selective oxidation of alcohol-d1to aldehyde-d1using MnO2
Kitsuwa, Kohei,Kumadaki, Katsushi,Nakayama, Atsushi,Okamura, Hironori,Ozawa, Keita,Shinada, Tetsuro,Tamura, Yusaku,Yamamoto, Yuki,Yasuno, Yoko
, p. 28530 - 28534 (2021/09/22)
The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald
Method for synthesizing chiral deuterated primary alcohol
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Paragraph 0031-0036; 0049-0053, (2021/05/29)
The invention discloses a method for synthesizing chiral deuterated primary alcohol. The method comprises the following step: reacting an aldehyde compound in an aprotic organic solvent at room temperature under the action of a chiral cobalt catalyst by t
Direct Detection of Hardly Detectable Hidden Chirality of Hydrocarbons and Deuterated Isotopomers by a Helical Polyacetylene through Chiral Amplification and Memory
Maeda, Katsuhiro,Hirose, Daisuke,Okoshi, Natsuki,Shimomura, Kouhei,Wada, Yuya,Ikai, Tomoyuki,Kanoh, Shigeyoshi,Yashima, Eiji
supporting information, p. 3270 - 3276 (2018/03/13)
We report the first direct chirality sensing of a series of chiral hydrocarbons and isotopically chiral compounds (deuterated isotopomers), which are almost impossible to detect by conventional optical spectroscopic methods, by a stereoregular polyacetyle
Springloaded porphyrin NHC hybrid rhodium(iii) complexes: Carbene dissociation and oxidation catalysis
Olguin, Juan,Mueller-Bunz, Helge,Albrecht, Martin
supporting information, p. 3488 - 3490 (2014/03/21)
Porphyrin rhodium(iii) complexes accommodate one or two NHC ligands in the apical position, which leads to severe porphyrin distortion and dearomatization. The strain in the bis(carbene) complex induces facile carbene dissociation and the formation of a catalytically active site for alcohol oxidation.
Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine
Barnett, Derek W.,Refaei, Maryanne S.,Curley Jr., Robert W.
, p. 6 - 11 (2013/03/28)
Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright
New synthesis and tritium labeling of a selective ligand for studying high-affinity γ-hydroxybutyrate (GHB) binding sites
Vogensen, Stine B.,Marek, Ale?,Bay, Tina,Wellendorph, Petrine,Kehler, Jan,Bundgaard, Christoffer,Fr?lund, Bente,Pedersen, Martin H. F.,Clausen, Rasmus P.
supporting information, p. 8201 - 8205 (2013/11/06)
3-Hydroxycyclopent-1-enecarboxylic acid (HOCPCA, 1) is a potent ligand for the high-affinity GHB binding sites in the CNS. An improved synthesis of 1 together with a very efficient synthesis of [3H]-1 is described. The radiosynthesis employs in
Deuterium isotope effect on bulk heterojunction solar cells. Enhancement of organic photovoltaic performances using monobenzyl substituted deuteriofullerene acceptors
Lu, Shirong,Jin, Tienan,Yasuda, Takeshi,Si, Weili,Oniwa, Kazuaki,Alamry, Khalid A.,Kosa, Samia A.,Asiri, Abdullah Mohamed,Han, Liyuan,Yamamoto, Yoshinori
supporting information, p. 5674 - 5677 (2013/12/04)
A series of novel monobenzyl-substituted deuteriofullerenes (BnDCs) were synthesized efficiently through Co-catalyzed selective monofunctionalization of C60. Bulk heterojunction solar cells, based on poly(3-hexylthiophene) as the donor and BnDC
Stereoselective hydride transfer by aryl-alcohol oxidase, a member of the GMC superfamily
Hernandez-Ortega, Aitor,Ferreira, Patricia,Merino, Pedro,Medina, Milagros,Guallar, Victor,Martinez, Angel T.
body text, p. 427 - 435 (2012/06/30)
Primary alcohol oxidation by aryl-alcohol oxidase (AAO), a flavoenzyme providing H2O2 to ligninolytic peroxidases, is produced by concerted proton and hydride transfers, as shown by substrate and solvent kinetic isotope effects (KIEs). Interestingly, when the reaction was investigated with synthesized (R)- and (S)-α-deuterated p-methoxybenzyl alcohol, a primary KIE (≈6) was observed only for the R enantiomer, revealing that the hydride transfer is highly stereoselective. Docking of p-methoxybenzyl alcohol at the buried crystal active site, together with QM/MM calculations, showed that this stereoselectivity is due to the position of the hydride- and proton-receiving atoms (flavin N5 and His502 Nε, respectively) relative to the alcohol Cα-substituents, and to the concerted nature of transfer (the pro-S orientation corresponding to a 6 kcalmol-1 penalty with respect to the pro-R orientation). The role of His502 is supported by the lower activity (by three orders of magnitude) of the H502A variant. The above stereoselectivity was also observed, although activities were much lower, in AAO reactions with secondary aryl alcohols (over 98% excess of the R enantiomer after treatment of racemic 1-(p-methoxyphenyl)ethanol, as shown by chiral HPLC) and especially with use of the F501A variant. This variant has an enlarged active site that allow better accommodation of the α-substituents, resulting in higher stereoselectivity (S/R ratios) than is seen with AAO. High enantioselectivity in a member of the GMC oxidoreductase superfamily is reported for the first time, and shows the potential for engineering of AAO for deracemization purposes.
Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: Insights into the effect of naphthoquinone
Yin, Guoyin,Wu, Yichen,Liu, Guosheng
supporting information; experimental part, p. 11978 - 11987 (2010/11/02)
Palladium-catalyzed oxidative amination of unactivated alkyl olefins has been developed to produce linear (E)-allylimides with high regioselectivity. This highly efficient transformation of alkenes has been achieved by enhancing the reoxidation of palladi