- Propenyl-1,3-sultone preparation method
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The invention discloses a propenyl-1,3-sultone preparation method which comprises the steps: firstly, preparing and obtaining 1,1-dichloroethane sulfonic acid through sulfonation addition reaction of1,1-dichloroethylene and obtaining 1,1-dichloroethane methyl sulfonate by esterifying the 1,1-dichloroethane sulfonic acid and methyl alcohol; further, catalytically cyclizing the 1,1-dichloroethane methyl sulfonate; finally, obtaining the propenyl-1,3-sultone through triethylamine catalysis elimination reaction. The propenyl-1,3-sultone preparation method disclosed by the invention has the advantages of economy and easiness in obtaining the raw materials, low toxicity, moderate reaction, simpleness in product separation, high yield and suitability for industrial production.
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Paragraph 0028-0029; 0032-0033; 0036-0037
(2018/04/21)
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- Method for synthesizing 1,3-propylene sulfonate
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The invention discloses a method for synthesizing 1,3-propylene sulfonate. The method comprises the following steps: 1) synthesizing 1-chlorine propylene glycol; 2) synthesizing propargyl alcohol; 3)synthesizing 3-hydroxypropylene sulfonic acid; and 4) synthesizing 1,3-propylene sulfonate. According to the method, the synthesis path is simple, the raw materials are low-cost and easily acquired, the compounding cost is low and the yield is high.
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Paragraph 0036; 0045-0046
(2018/04/01)
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- Preparation method of propenyl-1,3-propane sultone
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The invention discloses a preparation method of propenyl-1,3-propane sultone. The preparation method comprises the following steps: (1) enabling propargyl alcohol and hydrosulfite to be subjected to free radical addition reaction in water under the existence of an amine compound and an initiating agent or under the irradiation of ultraviolet light to generate 3-hydroxyl-1-propylene sulfonate, acidifying and preparing 3-hydroxyl-1-propylene sulfonic acid; (2) then enabling the 3-hydroxyl-1-propylene sulfonic acid to be subjected to cyclization reaction at a vacuum degree of 0-10 mmHg and a temperature of 80-150 DEG C under the action of a catalyst to generate the propenyl-1,3-propane sultone. The preparation method disclosed by the invention can reduce the environmental pollution, is more environmentally-friendly, and has the advantages of being simple to operate, safe, more ideal in yield and the like.
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Paragraph 0030; 0034; 0035; 0039; 0040; 0044
(2018/10/19)
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- A method for preparing 1,3-prop-1-ene sultone
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The present invention provides a novel method for producing 1,3-prop-1-ene sultone. The production method of the present invention is economical due to an inexpensive reagent and can be produced with high purity and high yield in mild conditions, thereby being able to be easily applied to mass production.COPYRIGHT KIPO 2017
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Paragraph 0074-0075
(2017/11/03)
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- Preparation method of allyl-1,3-sultone
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The invention discloses a preparation method of allyl-1,3-sultone. The method comprises the following steps: 1) halogenation reaction: in a condition of catalyst or illumination, enabling 1,3-propane sultone and a brominating agent to react in a micro-channel reactor or a tubular reactor to obtain 2-bromo-1,3-propane sultone; 2) elimination reaction: in a reflux reaction device, removing hydrogen bromide of the 2-bromo-1,3-propane sultone obtained in the step 1) under the effect of a dehalogenation agent and a polymerization inhibitor till reaction is completed; and 3) concentration and crystallization: adding active carbon into the reaction system of the step 2) for decoloration; after the decoloration, filtering out the active carbon; and performing concentration and crystallization to obtain the allyl-1,3-sultone. According to the preparation method disclosed by the invention, electronic-grade 1,3-propane sultone is used as a raw material, and the allyl-1,3-sultone is synthesized through halogenation and elimination reactions; and the reaction process is in stable control, the requirements on equipment are not high, the reaction selectivity is good, the product yield is high, few three wastes are produced, the cost is low, and the method is suitable for industrial production.
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Paragraph 0064; 0066
(2017/04/27)
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- A 1 - propenyl - 1, 3 - sulfonic acid lactone preparation method
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The invention relates to a preparation method of 1-propenyl-1,3-sultone. The method comprises the following steps: propargyl alcohol and pre-treated anion exchange resin are added to an aqueous solution of hydrosulphite, air is introduced, the mixture is heated and stirred, and heat preservation reaction is performed, and a mixed solution is obtained; the obtained mixed solution is cooled and filtered to obtain filtrate and a filter cake; a chromatographic column is filled with the filter cake and leached with protonic acid, leacheate is collected and distilled to obtain a brown and thick liquid; the obtained brown and thick liquid is cooled to the room temperature and subjected to decompression dehydration to obtain 1-propenyl-1,3-sultone. The preparation method provides possibility for large-scale industrial production.
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Paragraph 0034; 0039; 0044
(2017/05/02)
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- Enantioselective template-directed [2+2] photocycloadditions of isoquinolones: Scope, mechanism and synthetic applications
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A strategy for the enantioselective [2+2] photocycloaddition of isoquinolones with alkenes is presented, in which the formation of a supramolecular complex between a chiral template and the substrate ensures high enantioface differentiation by shielding one face of the substrate. Fifteen different electron-deficient alkenes and ten different substituted isoquinolones undergo efficient photocycloaddition, yielding the cyclobutane products in excellent yields and with outstanding regio-, diastereo- and enantioselectivities (up to 990 ee). The mechanism of the reaction is investigated by means of triplet sensitization/quenching and radical clock experiments, the results of which are consistent with the involvement of a triplet excited state and a 1,4-biradical intermediate. The variety of functionalized cyclobutanes obtained using this approach can be further increased by straightforward synthetic transformations of the photoadducts, allowing rapid access to libraries of compounds for various applications.
- Coote, Susannah C.,P?thig, Alexander,Bach, Thorsten
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supporting information
p. 6906 - 6912
(2015/04/27)
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- METHOD FOR PRODUCING CYCLIC SULFONIC ACID ESTER AND INTERMEDIATE THEREOF
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The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.
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Page/Page column 11
(2012/06/01)
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- Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole
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Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, β,γ-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven-membered ring β,γ-unsaturated sultones were converted into homoallylic conjugated (Z)-dienols. This methodology was applied to the racemic synthesis of the originally proposed structure of the marine natural product mycothiazole.
- Le Flohic, Alexandre,Meyer, Christophe,Cossy, Janine
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p. 9017 - 9037
(2007/10/03)
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- Methods and compositions for treating amyloid-related diseases
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Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
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Page/Page column 172-173
(2010/11/24)
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- Ring closing metathesis in the synthesis of sultones and sultams
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Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis (RCM) of sulfonates. The resulting α,β-unsaturated sultones act as dienophiles in intermolecular Diels-Alder reactions. A first cyclic sulfate formation through RCM has been discovered, and a rapid access to β-lactams fused to a sultam moiety of variable ring size was developed from inexpensive, commercially available starting materials using RCM as the key operation. An efficient RCM of 4-vinyl-azetidin-2-ones to give 1-aza-bicyclo[4.2.0]oct-4-en-8-ones is also described.
- Karsch, Sandra,Freitag, Dirk,Schwab, Pia,Metz, Peter
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p. 1696 - 1712
(2007/10/03)
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- Unsaturated Sultones from Unsaturated Sulfonates: Synthesis by Ring-Closing Metathesis and Reactivity
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Unsaturated sultones can be efficiently synthesized by ring-closing metathesis of the corresponding unsaturated sulfonates derived from primary and secondary alkenols or alkynols. These compounds can be converted to 1,3-dienes under basic conditions in the presence of carbenoid species.
- Flohic, Alexandre Le,Meyer, Christophe,Cossy, Janine,Desmurs, Jean-Roger,Galland, Jean-Christophe
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p. 667 - 670
(2007/10/03)
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- 1,3-Dipolar cycloaddition reactions of nitrones to prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1329 - 1334
(2007/10/03)
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- 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides to Prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone 1 with a variety of nitrile oxides 3 afforded novel [3+2] cycloaddition products 4 in good yield. The cycloaddition reaction achieved excellent regioselectivity.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1071 - 1074
(2007/10/03)
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- Synthesis of sultones by ring closing metathesis
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Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis of sulfonates. The required substrates were readily derived from alkenols and olefinic sulfonyl chlorides.
- Karsch, Sandra,Schwab, Pia,Metz, Peter
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p. 2019 - 2022
(2007/10/03)
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- Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts
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A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.
- Jiang, La Sheng,Chan, Wing Hong,Lee, Albert W. M.
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p. 2245 - 2262
(2007/10/03)
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- Synthesis of 1-alkene-1,3-sultones from 2,3-epoxy-alkanesulfonyl chlorides
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Dehydrochlorination of αβ-epoxy sulfonyl chlorides 3 leads to 1-alkene-1,3-sultones 1 most probably via epoxy sulfenes 2.
- Bonini, Bianca F.,Kemperman, Gerjan,Willems, Sander T.H.,Fochi, Mariafrancesca,Mazzanti, Germana,Zwanenburg, Binne
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p. 1411 - 1413
(2007/10/03)
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- Synthesis and Diels-Alder reactions of α,β-unsaturated γ-sultone
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An efficient synthesis of prop-1-ene 1,3-sultone 1 and its Diels-Alder reactions are reported; ring-opening reactions of the cycloadducts with nucleophiles and transformations to the sultams were also investigated.
- Lee, Albert W. M.,Chan,Jiang,Poon
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p. 611 - 612
(2007/10/03)
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