3516-65-2Relevant academic research and scientific papers
A Rubrolide synthetic method of compound (by machine translation)
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Paragraph 0077; 0080, (2019/05/02)
The invention discloses a Rubrolide synthetic method of compound, comprises the following steps: (1) under the action of the phosphate, substituted phenylacetaldehydes and chloroacetic acid obtained through the reaction of intermediate 1; (2) the intermediate 1 with NaBH4 Reduction reaction, reduction reaction product is then purged acid dehydration reaction to obtain the intermediate 2; (3) under the action of alkali, the intermediate 2 and substituted benzene formaldehyde reflux reaction to obtain the target product. The present invention provides synthetic method of compound Rubrolide using substituted phenylacetaldehydes, glyoxalic acid, phosphoric acid, NaBH4 And concentrated sulfuric acid as the raw materials, raw materials are cheap, easy to obtain, the synthetic method is simple, mild reaction, compared with the traditional synthetic method, not only to avoid expensive raw materials and a noble metal catalyst, greatly reduces the production cost, and also avoids the harsh reaction conditions; and the mild reaction conditions, the operation is simple, friendly to the environment, the solvent is easily recovered, is suitable for industrial production. (by machine translation)
Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides
Karak, Milandip,Barbosa, Luiz C.A.,Maltha, Celia R.A.,Silva, Thiago M.,Boukouvalas, John
supporting information, p. 2830 - 2834 (2017/06/27)
Several α-unsubstituted β-arylbutenolides have been prepared in 69–92% yield by reductive dehalogenation of α-halo-β-arylbutenolides. The latter were assembled in a single-step from α,β-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3″-bromorubrolide F.
Synthetic method for rubrolide compounds E, F, R, S and their derivatives
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Paragraph 0109; 0110, (2018/03/28)
Rubrolide F (compound 1f), R (compound 1r), and S (compound 1s), which are biological important natural butenolides, 7andPrime;,8andPrime;-didihydro derivatives (compound 1sa) thereof, 3andPrime; -bromorubrolide (compound 1fa), rubrolide E (compound 1e) and di-O-methyl derivatives thereof (compound 1ea) can be industrially obtained and are effectively synthesized with the overall yield of 14-48.5% from low-priced precursors. The rubrolide compounds can be synthesized through a Knoevenagel condensation reaction after a Wittig-Horner reaction and SeO_2-induced tandem allylic hydroxylation/intramolecular cyclization for preparing butenolide rings and a rubrolide cores structure.COPYRIGHT KIPO 2017
Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones
Kiyokawa, Kensuke,Takemoto, Kenta,Yahata, Shunsuke,Kojima, Takumi,Minakata, Satoshi
supporting information, p. 2907 - 2912 (2017/06/27)
The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.
Efficient, collective synthesis and nitric oxide inhibitory activity of rubrolides E, F, R, S and their derivatives
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 50 - 53 (2016/12/23)
An efficient first synthesis of biologically significant natural butenolides, rubrolides F (1f), R (1r), S (1s) & its 7″,8″-didehydro derivative (1sa), and 3″-bromo rubrolide (1fa) along with the synthesis of rubrolide E (1e) and its di-O-methyl derivative (1ea) is accomplished in a collective fashion from commercially available and inexpensive precursors in overall yields of 14–48.5%. Key features are Wittig-Horner reaction, SeO2-induced tandem allylic hydroxylation/intramolecular cyclization and Knoevenagel condensation. Next, in their inhibitory activity towards nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity, all compounds displayed good inhibitory activity in a concentration-dependent manner. None of the compound exhibited notable cytotoxicity at the highest concentration (10?μM) and IC50values are found in the range from 8.53 to 17.85?μM.
BUTENOLIDES, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
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Paragraph 0229-0232, (2021/06/01)
The present invention relates to: a butenolide-based compound; a stereoisomer thereof; an enantiomer thereof; an in vivo hydrolyzable precursor thereof or a pharmaceutically acceptable salt thereof; and the antibacterial activity, immune disease treatment; and prevention efficacy, the cancer prevention or treatment efficacy, and the preventive activity with respect to the fouling of a medical insertion instrument thereof.
Hg/Pt-catalyzed conversion of bromo alkynamines/alkynols to saturated and unsaturated γ-butyrolactams/lactones via intramolecular electrophilic cyclization
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Maddi Sridhar
, p. 1252 - 1260 (2016/02/03)
Convenient and general Hg(ii)/Pt(iv) catalyzed syntheses of γ-butyrolactams and α,β-unsaturated γ-butyrolactones/lactams are described via intramolecular electrophilic cyclizations of bromoalkynes with tosylamino and hydroxyl tethers. The reaction features the use of wet solvents, the exclusion of any base and additive, mild conditions and practical yields. We also synthesised few chiral lactams through this pathway. Additionally, it is shown that the NHTs group distanced further from the homopropargylic position assists regioselective bromoalkyne hydration to yield useful α-bromoketones. Furthermore, Boc protected bromo homo propargyl amines undergo 6-endo-dig cyclization through Boc oxygen to give bromomethylene substituted oxazinones.
New concise and efficient synthesis of rubrolides C and e via intramolecular Wittig reaction
Tale, Nilesh P.,Shelke, Amol V.,Tiwari, Girdharilal B.,Thorat, Prerana B.,Karade, Nandkishor N.
, p. 852 - 857 (2012/06/16)
A short total synthesis of rubrolides C and E has been achieved in four steps, using readily available 4-methoxyacetophenone, 2-bromoacetic acid, and the appropriate aromatic aldehyde, in 46 and 45% yield, respectively. Key reactions involved are α-tosyloxylation of the aryl methyl ketone, intramolecular Wittig reaction, Knoevenagel condensation, and demethylation. Copyright
Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation
Hu, Yi,Ding, Qiuping,Ye, Shengqing,Peng, Yiyuan,Wu, Jie
supporting information; experimental part, p. 7258 - 7262 (2011/10/08)
An efficient palladium-catalyzed cross-coupling reaction of 4-hydroxy-pyrone or 4-hydroxy-2(5H)-furanone with arylboronic acid is described, which affords the 4-substituted-pyrones and 2(5H)-furanones in good yields. This transformation proceeds through a C-OH bond activation under mild conditions.
Synthesis and reactivity of β,γ-dihalogenated unsaturated acids: Application to the synthesis of 4-substituted 5 H -furan-2-ones
Lamande-Langle,Ngi, S. Inack,Anselmi,Allouchi,Duchene,Abarbri,Thibonnet
experimental part, p. 154 - 160 (2011/02/28)
β,γ-Dihalogenated unsaturated acids were prepared regio- and stereoselectively from allenic acid, and some aspects of their reactivities were studied. Georg Thieme Verlag Stuttgart · New York.
