14209-41-7Relevant articles and documents
Melera et al.
, p. 3705 (1964)
Design and pharmacology of quinuclidine derivatives as M2-selective muscarinic receptor ligands
Boehme, Thomas M.,Keim, Christine,Dannhardt, Gerd,Mutschler, Ernst,Lambrecht, Guenter
, p. 1241 - 1243 (2001)
In our search for M2-selective muscarinic receptor antagonists, we synthesized 1,3-disubstituted indenes. The effects of different basic moieties with regard to binding and selectivity towards the five distinct muscarinic receptor subtypes were investigated. The results show that the quinuclidine series afforded the most promising compounds in terms of both receptor affinity and M2-subtype selectivity.
Synthesis of 1-fluoroindan-1-carboxylic acid (FICA) and its properties as a chiral derivatizing agent
Takahashi, Tamiko,Kameda, Hiroaki,Kamei, Tomoyo,Ishizaki, Miyuki
, p. 760 - 768 (2006)
1-Fluoroindan-1-carboxylic acid (FICA) (1) was designed and synthesized as its methyl ester (FICA Me ester) (4) in order to develop an efficient chiral derivatizing agent (CDA) which excels α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA) in capability. FICA Me ester (4) was prepared by fluorination of methyl 1-hydroxyindan-1-carboxylate (3) with (diethylamino)sulfur trifluoride (DAST) and derived to the esters of racemic secondary alcohols by ester exchange reaction. The resulting ΔδF value was large in the case of 2-butyl ester of FICA (5a), whereas not detectable in the case of the corresponding MTPA ester (6a). The magnitude of the ΔδH values was similar to that of MTPA esters. The diastereomers of (R)-(-)-8-phenylmenthyl ester of FICA (5i) was separated and their 1H NMR analyses revealed that the concept of the modified Mosher's method was successfully applied to 5i.
Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases
Sandoval, Braddock A.,Clayman, Phillip D.,Oblinsky, Daniel G.,Oh, Seokjoon,Nakano, Yuji,Bird, Matthew,Scholes, Gregory D.,Hyster, Todd K.
supporting information, p. 1735 - 1739 (2021/01/25)
Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.
From Carbodiimides to Carbon Dioxide: Quantification of the Electrophilic Reactivities of Heteroallenes
Li, Zhen,Mayer, Robert J.,Ofial, Armin R.,Mayr, Herbert
supporting information, p. 8383 - 8402 (2020/05/22)
Kinetics of the reactions of isocyanates, isothiocyanates, carbodiimides, carbon disulfide, and carbon dioxide with carbanions or enamines (reference nucleophiles) have been measured photometrically in acetonitrile or DMSO solution at 20 °C. The resulting second-order rate constants and the previously published reactivity parameters N and sN of the reference nucleophiles were substituted into the correlation log k2(20 °C) = sN(N + E) to determine the electrophilicity parameters of the heteroallenes: TsNCO (E = -7.69) ? PhNCO (E = -15.38) > CS2 (E = -17.70) ≈ PhNCS (E = -18.15) > PhNCNPh (E = -20.14) ? CyNCNCy (E ≈ -30). An approximate value could be derived for CO2 (-16 E - 11). Quantum chemical calculations were performed at the IEFPCM(DMSO)/B3LYP-D3/6-311+G(d,p) level of theory and compared with experimental Gibbs activation energies. The distortion-interaction model was used to rationalize the different reactivities of O- and S-substituted heteroallenes. Eventually it is demonstrated that the electrophilicity parameters determined in this work can be used as ordering principle for literature-known reactions of heteroallenes.
Dynamic enzymatic kinetic resolution of methyl 2,3-dihydro-1h-indene-1- carboxylate
Pietruszka, Joerg,Simon, Robert Christian,Kruska, Fabian,Braun, Manfred
experimental part, p. 6217 - 6224 (2010/03/26)
A new reaction setup for kinetic enzymatic resolution was established and is demonstrated for the case of the hydrolase-catalysed conversion of methyl 2,3-dihydro-1H-indene1-carboxylate (1) in conjunction with a base-catalysed racemisation. The system allows controlled racemisation, resulting in efficient dynamic kinetic resolution (DKR) of the title compound. Short reaction times and high enantio-selectivities were obtained with CAL-B and TBD (1,5,7-triazabicyclo[4,4.0]dec-5-ene). Compound (R)-1 (ee 95%) served as a starting material in a domino reaction that led to the biaryl indanyl ketone (R)-8, a lead compound for novel inhibitors of peptidyl-prolyl-cis/irans- isomerases, in 94 % ee. Wiley-VCH Verlag GmbH & Co. KGaA,.
