3521-91-3Relevant academic research and scientific papers
A fortuitously straightforward synthesis of 4-acetoxy-2-propyltetrahydrothiophene
Ma, Bianbian,Yang, Shaoxiang,Tao, Feiyan,Sun, Baoguo,Liu, Yongguo,Tian, Hongyu
, p. 724 - 726 (2015)
4-Acetoxy-2-propyltetrahydrothiophene was synthesised from 1-hepten-4-ol by a three-step route involving epoxidation and mesylation to 1,2-epoxy-4-heptyl mesylate and then reaction with thioacetate. An acetoxylated cyclic product was formed instead of the expected thioacetate, and a mechanism for its formation using an intramolecular transesterification is proposed.
Synthesis of a new odourant, 2-mercapto-4-heptanol
Yang, Shaoxiang,Gong, Wei,Sun, Baoguo,Liu, Yongguo,Tian, Hongyu
, p. 184 - 186 (2015)
2-Mercapto-4-heptanol is a relatively new flavour compound that was recently approved as an ingredient by the Flavour and Extract Manufacturers' Association in 2013. Its synthesis, which we have accomplished in four-steps, involved firstly a Grignard reaction of n-butanal with allylmagnesium chloride to prepare 1-hepten-4-ol. This was epoxidised and then converted to 1,2-epithio-4-heptanol, reduction of which with LiAlH4 gave the target compound in an overall yield of about 54%.
Toward creation of a universal NMR database for stereochemical assignment: The case of 1,3,5-trisubstituted acyclic systems
Kobayashi, Yoshihisa,Tan, Choon-Hong,Kishi, Yoshito
, p. 2562 - 2571 (2000)
Using the diastereoisomeric triols 1a-d (Fig. 1) and examples summarized in Fig. 2, the central C-atom of acyclic 1,3,5-triols is demonstrated to exhibit a distinctive chemical shift that is dependent on the 1,3- and 3,5-relative configuration, but is independent of the functionalities present outside of this structural motif. These NMR characteristics are then used to predict the relative configuration of several natural products (Fig, 7). In addition, an example is given to show the possibility of assembling an NMR database for a larger array of functional groups from NMR databases of smaller arrays of functional groups.
Method for synthesizing 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring
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Paragraph 0018-0023; 0025, (2019/10/01)
The invention discloses a method for synthesizing 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring. The synthesis method includes the following steps: performing Grignard reaction on an aldehyde or ketone to obtain an allyl alcohol compound; and performing condensation reaction with 2-(tert-butylsulfonyl)acetic acid to obtain an allyl (tert-butylsulfonyl)acetate compound; performing olefin cross-metathesis reaction under the action of a second generation Grubbs catalyst to obtain a methoxycarbonyl (tert-butylsulfonyl)acetate compound; performing intramolecular reaction byusing anhydrous N,N-dimethylformamide as a solvent in the presence of a catalyst palladium acetate and a ligand triphenylphosphine, so as to produce a 3-tert-butylsulfonyl 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring lactone compound; and finally removing tert-butylsulfonyl in a reaction solution of sodium amalgam and acetic acid by taking ethanol as a solvent, so as toobtain 8th-site substituted-3,4,7,8-tetrahydro-2H-oxocin-2-one octatomic ring lactone compound. The yield of the method is high, and a solution with a very dilute reaction concentration is not neededin the synthesis of various substituted octatomic ring lactones through intramolecular catalysis by palladium, so the process conditions are simple and universal.
Oxa/thiazole-tetrahydropyran triazole-linked hybrids with selective antiproliferative activity against human tumour cells
Valdomir, Guillermo,Fernández,Lagunes, Irene,Padrón, Juan I.,Martín, Víctor S.,Padrón, José M.,Davyt, Danilo
supporting information, p. 13784 - 13789 (2018/08/21)
Inspired by diverse marine bioactive compounds, the principle of molecular hybridization was applied to produce a series of new compounds combining diverse heterocyclic systems (oxa/thiazoles and tetrahydropyrans) via a triazole ring, attempting to increase the activity of individual building blocks. These new compounds exhibit a highly interesting antiproliferative activity against different human tumour cells and good selectivity when compared to normal cells. The formation of reactive oxygen species and the interaction with P-gp were also evaluated for the lead compounds.
Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
Allais, Christophe,Roush, William R.
supporting information, p. 2646 - 2649 (2017/05/24)
A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with (diisopinocampheyl)borane 4. This strategy was applied to the total synthesis of andrachcine 1, thus establishing with certainty the absolute and relative configuration of the natural product.
Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation
Punganuru, Surendra R.,Aviraboina, Sivaprasad,Srivenugopal, Kalkunte S.
, p. 375 - 378 (2016/07/06)
A concise stereoselective total synthesis of (+)-monocerin has been accomplished using cross metathesis, tandem dihydroxylation-SN2 cyclisation and intramolecular alkoxycarbonylation as key steps. Cross-metathesis of 2-iodo-3,4,5-trimethoxyvinylbenzene and (R)-hepten-4-ol, followed by tandem dihydroxylation-SN2 cyclisation generated a tri-substituted tetrahydrofuran ring. Finally, the dihydroisocoumarin was obtained by an intramolecular alkoxycarbonylation. In this paper, we have developed an expedient operationally simple Pd(OAc)2/bathocuproine catalysed alkoxycarbonylation under atmospheric pressure of carbon monoxide. The catalytic system developed here can be useful for the synthesis of various dihydroisocoumarins and phthalides.
Synthesis of homoallylic amines and acylhydrazides by tin powder-promoted multicomponent one-pot allylation reactions
Ma, Junyan,Huang, Danfeng,Wang, Ke-Hu,Xu, Yanli,Chong, Siying,Su, Yingpeng,Fu, Ying,Hu, Yulai
, p. 571 - 576 (2016/07/16)
An efficient process for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from the one-pot reaction of carbonyl compounds, amines or N-acylhydrazines, allyllic bromide and tin powder using water as solvent. N-Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides. Copyright
A ionic the bistriphenyl make PVC possess enough preparation and application of (V) complex
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Paragraph 0068; 0069, (2017/01/02)
The invention provides a preparation method of an ionic type bis-triphenyl organic antimony (V) complex and a method for synthesizing allyl alcohol compounds under catalysis of the ionic type bis-triphenyl organic antimony (V) complex. The complex is a cationic type organic antimony complex, wherein two antimony atoms in the complex are bridged by virtue of oxygen atoms and are pentavalent; and each antimony atom is in coordination with one water molecule, and an ionic bond is formed by the entire organic antimony cationic part with corresponding anions. The synthetic method comprises the following step: by taking the bis-triphenyl organic antimony (V) complex as a catalyst, taking a commonly-used organic solvent as a reaction solvent, and taking aldehyde and tetraallyltin as raw materials, performing reaction. The synthetic method can be used for providing a novel low-cost and 'green' route for preparing the allyl alcohol compounds, and has the advantages that target product selectivity and yield are high, the catalyst can be repeatedly used, corresponding ketone can be obtained by performing simple column chromatography separation on the product, and the whole reaction and separation process is simple to operate and is green and environment-friendly.
Synthesis of active tin: An efficient reagent for allylation reaction of carbonyl compounds
Sinha, Arun Kumar,Sil, Amit,Sasmal, Anup Kumar,Pradhan, Mukul,Pal, Tarasankar
, p. 1685 - 1690 (2015/03/30)
High purity Sn(0) has been obtained as a result of reduction of SnO by sodium stannite (Na2SnO2) in aqueous solution. The process stands unique for the production of tin metal. The as-synthesized tin finds applications in synthetic organic chemistry as a reagent for the allylation of aldehydes and ketones in distilled water at room temperature to give rise to the corresponding homoallylic alcohols with high yield. The reaction occurs without the assistance of heat, ultrasonic vibration, co-solvents/co-reagents, etc. Enhancement of the reaction rate of allylation was observed in water rather than THF. The manipulation of allylation reaction becomes easy with active tin material.
