4720-68-7Relevant academic research and scientific papers
Formal Asymmetric Catalytic Thiolation with a Bifunctional Catalyst at a Water-Oil Interface: Synthesis of Benzyl Thiols
Guo, Wengang,Wu, Bo,Zhou, Xin,Chen, Ping,Wang, Xu,Zhou, Yong-Gui,Liu, Yan,Li, Can
, p. 4522 - 4526 (2015)
The enantioselective conjugated addition of tritylthiol to in situ generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99%) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o-QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water-oil biphase is crucial for achieving high reactivity and stereoselectivity.
Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C-6 Position
Buravlev, Evgeny V.,Shevchenko, Oksana G.,Suponitsky, Kyrill Yu.
, (2021)
Several synthetic approaches (aminomethylation, alkylation, condensation, etc.) have been used to synthesize derivatives based on the sesamol (1), natural phenol. The set of methods, including the study of antioxidant activity (AOA) by the ability to inhibit the initiated oxidation of animal lipids, radical scavenging activity, Fe2+-chelation ability, as well as a comparative assessment of membrane-protective activity under the conditions of H2O2-induced hemolysis of mice red blood cells (RBCs), was used to analyze the antioxidant potential of the synthesized compounds. The synthesized derivatives have demonstrated different activity in the listed test systems, and we have identified compounds which appear to be most promising for a detailed study of their pharmacological properties.
Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens
Zhao, Yang,Ku, Chuen-Fai,Xu, Xin-Ya,Tsang, Nga-Yi,Zhu, Yu,Zhao, Chen-Liang,Liu, Kang-Lun,Li, Chuang-Chuang,Rong, Lijun,Zhang, Hong-Jie
, p. 5568 - 5583 (2021/05/07)
Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.
Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
Huang, You,Li, Xiaohu
supporting information, p. 9934 - 9937 (2021/10/12)
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
Diastereoselective Synthesis of Benzoxanthenones
Neuhaus, William C.,Kozlowski, Marisa C
supporting information, p. 1039 - 1043 (2020/03/13)
An oxidative catalytic vanadium(V) system was developed to access the naturally nonabundant diastereomers of carpanone from the corresponding alkenyl phenol monomer in one pot by tandem oxidation, oxidative coupling, and 4+2 cyclization. This system was applied to the synthesis of two other analogues of carpanone. Mild oxidizing silver salts were used as the terminal oxidant to minimize background oxidation which produces the natural diastereomer of carpanone. Further, the first examples of enantioselective oxidative benzoxanthenone formation are reported. Solvent polarity has a strong effect on enantioselectivity, consistent with a mechanism involving binding of vanadium Schiff base catalysts to the alcoholic moiety of the alkenyl phenols during the cyclization step.
An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans
Carre?o-Montero, Ariel,Maldonado, Luis A.,Chávez, María Isabel,Hernández-Ortega, Simón,Delgado, Guillermo
, (2019/11/03)
The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.
Phenyl benzofuran compound as well as preparation method, composition, and medical applications thereof
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Paragraph 0075-0077; 0081; 0084; 0088; 0091; 0095, (2019/01/08)
The invention discloses a phenyl benzofuran compound as well as a preparation method, a composition, and medical applications thereof. The structure of the phenyl benzofuran compound is: characterizedin that the formulas are shown in the specificationdescription. The invention discloses a traditional Chinese medicine extracting method of the phenyl benzofuran compound using a moonseed rhizomerhizoma menispermirough powder as a raw material.The invention discloses a chemical synthetic method of phenyl benzofuran compound using 2,4-dihydroxybenzoic acid as starting materials.The invention discloses a composition containing the phenyl benzofuran compound, and an active ingredient of the composition is the phenyl benzofuran compound.The invention also discloses the application of the phenyl benzofuran compound in the preparation of a drug or food or health product preventing or treating a tumor, and the tumor is nasopharyngeal carcinoma.According to the invention, the phenyl benzofuran compound can be prepared by the traditional Chinese medicine extracting method and the chemical synthetic method, and meanwhile, an in vitro tumor cell experiment proves that phenyl benzofuran has an inhibiting effect on both nasopharyngeal carcinoma cells CNE-1 and CNE-2.
Chiral multi-substituted 4 - hydroxy chroman compound and its preparation method and application
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Paragraph 0211; 0212; 0213, (2017/07/01)
The invention discloses a chiral polysubstituted 4-hydroxychroman compound, and a preparation method and application thereof. The compound has a general structural formula as shown in a formula I which is described in the specification. The preparation method comprises a step of subjecting a salicylaldehyde compound as shown in a general structural formula II and a tertiary alkenyl amide as shown in a general structural formula III to an intermolecular nucleophilic tandem reaction in the presence of a chiral Lewis acid catalyst so as to realize high-efficiency high-selectivity preparation of the chiral polysubstituted 4-hydroxychroman compound. According to the method, the raw material alkenyl amide which can be easily prepared on large scale and the cheap and easily available chiral catalyst are used, and the novel chiral polysubstituted 4-hydroxychroman bicyclo derivative product which cannot be synthesized by using other methods is prepared under mild reaction conditions; and the produce has a stable structure, high yield and enantioselectivity and good application prospects and can be easily separated and purified.
Phosphine-Catalyzed [4 + 2] Annulation of Allenoate with Sulfamate-Derived Cyclic Imines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
Mao, Biming,Shi, Wangyu,Liao, Jianning,Liu, Honglei,Zhang, Cheng,Guo, Hongchao
supporting information, p. 6340 - 6343 (2017/12/08)
A phosphine-catalyzed [4 + 2] cycloaddition of cyclic α-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving γ′-carbon of α-substituted allenoate.
Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
Sun, Peng,Gao, Shang,Yang, Chi,Guo, Songjin,Lin, Aijun,Yao, Hequan
supporting information, p. 6464 - 6467 (2016/12/23)
A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C-H activation/decarbonylation/annulation process, while AcOH led to chromones through a C-H activation/annulation pathway. The reaction exhibited good functional group tolerance and scalability. Moreover, only a single regioisomer of benzofuran was obtained due to the in situ decarbonylation orientation effect.
