13101-88-7Relevant academic research and scientific papers
Synthesis and characterization of optically active cyclic 6,6'-dinitro-1,1-binaphthyl-2,2'-diethers
Van Es,Biemans,Meijer
, p. 1825 - 1831 (1997)
A series of racemic and enantiomerically pure 6,6'-dinitro-1,1'-binaphthyl 2,2'-diethers 1 have been synthesized by the nitration of the corresponding cyclic ethers and both the reactivity of nitration and the (chir)optical properties proved to be very sensitive for the chain length of the ether bridge.
Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core
Arae, Sachie,Mori, Takaaki,Kawatsu, Takahiro,Ueda, Daiki,Shigeta, Yusuke,Hamamoto, Nobutsugu,Fujimoto, Hitoshi,Sumimoto, Michinori,Imahori, Tatsushi,Igawa, Kazunobu,Tomooka, Katsuhiko,Punniyamurthy, Tharmalingam,Irie, Ryo
, p. 1214 - 1216 (2017)
A new hetero[7]helicene 1NN structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)2 and O2 as the key step. Significantly, 1NN was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1NN and DFT calculations on its variants revealed that the stereo-chemical stability of the benzodiheterole-based helicenes was highly dependent on not only the heteroaromatic ring component but also on the N-substituent of the pyrrole ring unit.
Evaluation of the stability of cucurbit[8]uril-based ternary host?guest complexation in physiological environment and the fabrication of a supramolecular theranostic nanomedicine
Wu, Han,Chen, Zuobing,Qi, Shaolong,Bai, Bing,Ye, Jiajun,Wu, Dan,Shen, Jie,Kang, Fei,Yu, Guocan
, (2021/10/25)
Background: Supramolecular theranostics have exhibited promising potentials in disease diagnosis and therapy by taking advantages of the dynamic and reversible nature of non-covalent interactions. It is extremely important to figure out the stability of the driving forces in physiological environment for the preparation of theranostic systems. Methods: The host?guest complexation between cucurbit[8]uril (CB[8]), 4,4′-bipyridinium, and napththyl guest was fully studied using various characterizations, including nuclear magnetic resonance spectroscopy, ultraviolet–visible (UV–vis) spectroscopy, isothermal titration calorimetry (ITC). The association constants of this ternary complex were determined using isothermal titration calorimetry. The stability of the non-covalent interactions and self-assemblies form from this molecular recognition was confirmed by UV–vis spectroscopy and dynamic light scattering (DLS). A supramolecular nanomedicine was constructed on the basis of this 1:1:1 ternary recognition, and its in vitro and in vivo anticancer efficacy were thoroughly evaluated. Positron emission tomography (PET) imaging was used to monitor the delivery and biodistribution of the supramolecular nanomedicine. Results: Various experiments confirmed that the ternary complexation between 4,4′-bipyridinium, and napththyl derivative and CB[8] was stable in physiological environment, including phosphate buffered solution and cell culture medium. Supramolecular nanomedicine (SNM@DOX) encapsulating a neutral anticancer drug (doxrubincin, DOX) was prepared based on this molecular recognition that linked the hydrophobic poly(ε-caprolactone) chain and hydrophilic polyethylene glycol segment. The non-covalent interactions guaranteed the stability of SNM@DOX during blood circulation and promoted its tumor accumulation by taking advantage of the enhanced permeability and retention effect, thus greatly improving the anti-tumor efficacy as compared with the free drug. Conclusion: Arising from the host-enhanced charge-transfer interactions, the CB[8]-based ternary recognition was stable enough in physiological environment, which was suitable for the fabrication of supramolecular nanotheranostics showing promising potentials in precise cancer diagnosis and therapy. Graphic Abstract: [Figure not available: see fulltext.].
Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes
Ji, Jieying,Jiang, Quanbin,Liang, Yaoyu,Luo, Jie,Zhang, Xiaoyan,Zhao, Xiaodan
supporting information, p. 4959 - 4964 (2020/02/11)
The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.
Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
Hyodo, Kengo,Hasegawa, Genna,Maki, Hiroya,Uchida, Kingo
supporting information, p. 2818 - 2822 (2019/04/25)
The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.
PRODUCTION METHOD OF PRIMARY AMINE COMPOUND
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Paragraph 0026; 0027; 0029, (2019/09/20)
PROBLEM TO BE SOLVED: To provide a simple production method of a primary amine compound unnecessary for complicated procedures and toxic sodium azide or the like. SOLUTION: A production method of a primary amine compound includes a step for reacting a ketone compound and an oxime compound in the presence of alcohol and an acid catalyst. Preferably, the acid catalyst is hydrochloric acid, sulfuric acid, methanesulfonic acid, camphorsulfonic acid, a tosyl acid hydrate, trifluoromethane sulfonic acid or a boron trifluoride diethyl ether complex. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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Paragraph 0098; 0134; 0135; 0147, (2018/03/25)
In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
NOVEL ORGANIC COMPOUND, NEAR-INFRARED FLUORESCENT CONSTANT MEDIUM CONTAINING SAME, AND METHOD FOR NANO-GRANULATING CONSTANT MEDIUM
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Paragraph 0109; 0110; 0111, (2018/12/04)
The present invention relates to a novel organic compound, a near-infrared fluorescent constant medium containing the same, and a method for nano-granulating the constant medium.
Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
Gao, Hongyin,Zhou, Zhe,Kwon, Doo-Hyun,Coombs, James,Jones, Steven,Behnke, Nicole Erin,Ess, Daniel H.,Kürti, László
, p. 681 - 688 (2017/06/30)
Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.
Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C?O and C?C Bond Activation
Yue, Huifeng,Guo, Lin,Liao, Hsuan-Hung,Cai, Yunfei,Zhu, Chen,Rueping, Magnus
supporting information, p. 4282 - 4285 (2017/04/03)
An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.
