122854-65-3Relevant articles and documents
Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
, p. 5699 - 5703 (2019/08/01)
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
Racemic gem disilyl alkane compound containing four silicon-hydrogen bonds, and sybthesis method and application of compound
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Paragraph 0263-0268; 0269, (2019/05/15)
The invention discloses a racemic gem disilyl alkane compound containing four silicon-hydrogen bonds. The compound is as shown in a formula IV. The invention further discloses a synthesis method of the racemic gem disilyl alkane compound. The synthesis method comprises the following step of carrying out a reaction by taking alkyne as shown in a formula I and trihydrosilane as shown in a formula IIas raw materials and taking a chiral CoX-IIP complex as a catalyst in the presence of a reducing agent to obtain the racemic gem disilyl alkane compound containing four silicon-hydrogen bonds, wherein the compound is as shown in the formula IV. The method disclosed by the invention has mild reaction conditions, is simple and convenient to operate and has high atom economy. In addition, the reaction does not need addition of any salts of toxic transition metals (such as ruthenium, rhodium, palladium and the like), and the method has a relatively large practical application value in synthesis of medicines and materials. In addition, the reaction has a medium to excellent yield (51-99%) and high area selectivity (10:1-19:1, most parts larger than 19:1).
Deacylative transformations of ketones via aromatization-promoted C–C bond activation
Xu, Yan,Qi, Xiaotian,Zheng, Pengfei,Berti, Carlo C.,Liu, Peng,Dong, Guangbin
, p. 373 - 378 (2019/05/22)
Carbon–hydrogen (C–H) and carbon–carbon (C–C) bonds are the main constituents of organic matter. Recent advances in C–H functionalization technology have vastly expanded our toolbox for organic synthesis1. By contrast, C–C activation methods that enable editing of the molecular skeleton remain limited2–7. Several methods have been proposed for catalytic C–C activation, particularly with ketone substrates, that are typically promoted by using either ring-strain release as a thermodynamic driving force4,6 or directing groups5,7 to control the reaction outcome. Although effective, these strategies require substrates that contain highly strained ketones or a preinstalled directing group, or are limited to more specialist substrate classes5. Here we report a general C–C activation mode driven by aromatization of a pre-aromatic intermediate formed in situ. This reaction is suitable for various ketone substrates, is catalysed by an iridium/phosphine combination and is promoted by a hydrazine reagent and 1,3-dienes. Specifically, the acyl group is removed from the ketone and transformed to a pyrazole, and the resulting alkyl fragment undergoes various transformations. These include the deacetylation of methyl ketones, carbenoid-free formal homologation of aliphatic linear ketones and deconstructive pyrazole synthesis from cyclic ketones. Given that ketones are prevalent in feedstock chemicals, natural products and pharmaceuticals, these transformations could offer strategic bond disconnections in the synthesis of complex bioactive molecules.
Chiral geminal disilyl alkane compound, synthesis method and applications thereof
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Paragraph 0204; 0205; 0206; 0207; 0208, (2019/01/14)
The present invention discloses a chiral geminal disilyl alkane compound, which is represented by a formula V, wherein * represents a chiral carbon atom in the formula V. The invention discloses a synthesis method of the chiral geminal disilyl alkane compound, wherein the synthesis method comprises: carrying out a reaction in the presence of a reducing agent by using alkyne represented by a formula I, dihydrosilane represented by a formula II and trihydrosilane represented by a formula III as raw materials and using Xantphos-CoBr2 and a chiral CoX2-OIP complex as catalysts under an inert gas to prepare the chiral geminal disilyl alkane compound represented by the formula V. According to the present invention, the method has characteristics of mild reaction condition, simple operation, highatomic economy, no requirement of the addition of any other toxic transition metals (such as ruthenium, rhodium, palladium and the like) salts, high yield and high enantioselectivity, and has great practical value in the synthesis of drugs and materials, wherein the yield is generally 50-85%, and the enantioselectivity is generally 93-99%. The formulas I, II, III and V are defined in the specification.
Direct Synthesis of Polysubstituted Aldehydes via Visible-Light Catalysis
Wu, Fengjin,Wang, Leifeng,Chen, Jiean,Nicewicz, David A.,Huang, Yong
supporting information, p. 2174 - 2178 (2018/02/06)
Aldehydes are among the most versatile functional groups for synthetic chemistry. However, access to polysubstituted alkyl aldehydes is very limited and requires lengthy synthetic routes that involve multiple-step functional-group conversion. This paper reports a one-step synthesis of polysubstituted aldehydes from readily available olefin substrates using visible-light photoredox catalysis. Despite a number of competing reaction pathways, commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen-atom-transfer catalyst under blue LED irradiation. Alkyl aldehydes with different substitution patterns are prepared in good yields. This strategy can be applied to structurally sophisticated substrates.
Targeting an Aromatic Hotspot in Plasmodium falciparum 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase with β-Arylpropyl Analogues of Fosmidomycin
Sooriyaarachchi, Sanjeewani,Chofor, René,Risseeuw, Martijn D. P.,Bergfors, Terese,Pouyez, Jenny,Dowd, Cynthia S.,Maes, Louis,Wouters, Johan,Jones, T. Alwyn,Van Calenbergh, Serge,Mowbray, Sherry L.
, p. 2024 - 2036 (2016/10/22)
Blocking the 2-C-methyl-d-erythrithol-4-phosphate pathway for isoprenoid biosynthesis offers new ways to inhibit the growth of Plasmodium spp. Fosmidomycin [(3-(N-hydroxyformamido)propyl)phosphonic acid, 1] and its acetyl homologue FR-900098 [(3-(N-hydroxyacetamido)propyl)phosphonic acid, 2] potently inhibit 1-deoxy-d-xylulose-5-phosphate reductoisomerase (Dxr), a key enzyme in this biosynthetic pathway. Arylpropyl substituents were introduced at the β-position of the hydroxamate analogue of 2 to study changes in lipophilicity, as well as electronic and steric properties. The potency of several new compounds on the P. falciparum enzyme approaches that of 1 and 2. Activities against the enzyme and parasite correlate well, supporting the mode of action. Seven X-ray structures show that all of the new arylpropyl substituents displace a key tryptophan residue of the active-site flap, which had made favorable interactions with 1 and 2. Plasticity of the flap allows substituents to be accommodated in many ways; in most cases, the flap is largely disordered. Compounds can be separated into two classes based on whether the substituent on the aromatic ring is at the meta or para position. Generally, meta-substituted compounds are better inhibitors, and in both classes, smaller size is linked to better potency.
