123171-29-9Relevant academic research and scientific papers
Design, Synthesis and Biological Evaluation of Highly Potent Simplified Archazolids
Rivière, Solenne,Vielmuth, Christin,Ennenbach, Christiane,Abdelrahman, Aliaa,Lemke, Carina,Gütschow, Michael,Müller, Christa E.,Menche, Dirk
, p. 1348 - 1363 (2020/06/17)
The archazolids are potent antiproliferative compounds that have recently emerged as a novel class of promising anticancer agents. Their complex macrolide structures and scarce natural supply make the development of more readily available analogues highly important. Herein, we report the design, synthesis and biological evaluation of four simplified and partially saturated archazolid derivatives. We also reveal important structure-activity relationship data as well as insights into the pharmacophore of these complex polyketides.
Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters
Hou, Shengtai,Yang, Hongjian,Cheng, Bin,Zhai, Hongbin,Li, Yun
supporting information, p. 6926 - 6929 (2017/07/10)
Cobaloxime (Co(dmgBF2)2·2H2O), an inexpensive first-row transition-metal complex, catalyzed hydration of terminal alkynes gave the corresponding methyl ketones in good to excellent yields under neutral conditions (additional protic acids and silver salts are not required). A wide range of functional groups, such as allyl ether, benzyl ethers, carboxylic esters, imides, amides, nitro, and halogens, were tolerated. The mild reaction conditions together with the inexpensive feature and easy availability of the catalyst well address the current challenges in the field of alkyne hydration.
Supported Gold Nanoparticle-Catalyzed Hydration of Alkynes under Basic Conditions
Liang, Shengzong,Jasinski, Jacek,Hammond, Gerald B.,Xu, Bo
supporting information, p. 162 - 165 (2015/07/28)
TiO2-supported nanosize gold particles catalyze the hydration of alkynes using morpholine as a basic cocatalyst. Unlike most homogeneous cationic gold catalysts, the TiO2-Au/morpholine system is weakly basic and is compatible with acid-sensitive functional groups (e.g., silyl ethers, ketals) or with a strongly coordinating group such as pyridine. What's more, this gold catalyst can be recycled by simple filtration and works well in flow reactors. (Chemical Equation Presented).
Hydration of terminal alkynes catalyzed by water-soluble cobalt porphyrin complexes
Tachinami, Tadashi,Nishimura, Takuho,Ushimaru, Richiro,Noyori, Ryoji,Naka, Hiroshi
supporting information, p. 50 - 53 (2013/02/23)
Water-soluble cobalt(III) porphyrin complexes were found to promote the hydration of terminal alkynes to give methyl ketones. The alkyne hydration proceeded in good to excellent yield with 0.1 to 2 mol % cobalt catalyst 1 and was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters; boronic esters; carboxamides; nitriles; and nitro, iodo, and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The alkyne hydration can be performed on a gram scale, and the catalyst can be recovered by aqueous workup.
Formation of α-hydroxyketones via irregular Wittig reaction
Okada, Hideki,Mori, Tomonori,Saikawa, Yoko,Nakata, Masaya
supporting information; experimental part, p. 1276 - 1278 (2009/09/05)
Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH4Cl at low temperature.
Isolable gold(I) complexes having one low-coordinating ligand as catalysts for the selective hydration of substituted alkynes at room temperature without acidic promoters
Leyva, Antonio,Corma, Avelino
scheme or table, p. 2067 - 2074 (2009/08/07)
Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)-phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones in nearly quantitative yields. Acid-labile groups present in the substrates are preserved. The catalytic activity strongly depends on both the nature of the phosphine coordinated to the gold (I) center and the softness of the counteranion, the complex AuSPhOsNTf2 showing the better activity. A plausible mechanism for the hydration of alkynes through ketal intermediates is proposed on the basis of kinetic studies. The described catalytic system should provide an efficient alternative to mercury-based methodologies and be useful in synthetic programs.
Intramolecular electron transfer initiated cation and radical formation through carbon-carbon bond activation
Wangyang, Tu,Floreancig, Paul E.
, p. 2389 - 2392 (2008/02/05)
Radical cations can be formed in a spatially and temporally controlled manner by appending a sacrificial photooxidant to an easily oxidized substrate, leading to intramolecular electron transfer upon irradiation. The anthraquinone carboxyl group is an effective photooxidant that can promote single electron oxidation from an appended arene. The resulting intermediates undergo a cleavage reaction through carbon-carbon bond activation to provide either cations or radicals that react to form a range of products.
Reactions of acylzirconocene chloride with nucleophiles: Bimodal reactivity at β- and acyl carbons of α,β-unsaturated acylzirconocene chloride
Hanzawa,Narita,Kaku-uchi,Taguchi
, p. 7525 - 7528 (2007/10/03)
Reactions of α,β-unsaturated acylzirconocene chloride with nucleophiles showed novel bimodal reactivity at the β- and acyl carbons depending upon the nucleophile employed, and the formation of ketone α,β-dianionic species was also observed. (C) 2000 Elsev
Novel oxepane formation by TiCl4-catalyzed nucleophilic cleavage of 1- alkoxymethyl-6,8-dioxabicyclo[3.2.1]octanes
Fujiwara, Kenshu,Amano, Arika,Tokiwano, Tetsuo,Murai, Akio
, p. 1065 - 1080 (2007/10/03)
Introduction of an alkoxymethyl group at the C1 position in the 6,8- dioxabicyclo[3.2.1]octane system enabled novel formation of oxepane compounds in TiCl-4-catalyzed acetal cleavage reactions. (C) 2000 Elsevier Science Ltd.
