CAS: 4233-33-4; 4-Phenyl-3H-1,2,4-Triazole-3,5(4H)-Dione

该化合物是高度反应的死灵和电死灵,广泛用于有机合成和点击化学应用.它与死灵的强烈反应使其成为Diels-Alder反应的宝贵试剂,使得不饱和化合物能够高效循环和功能化. PTAD由于它与富电性阿尔基内斯和 alkynes有选择性地反应,所以对生物分子的标签和修改特别有用. 化合物的晶体稳定性和定义明确的再活性特征增强了其在精确合成变异中的效用. 此外, PTAD是制作三环化合物的关键中间体,有助于制药和材料科学的进步. 它在温和条件下的强大性性表现进一步突出了它在实验室和工业环境中的多功能.

结构式图片

上下游产品

CAS号15988-11-1 4-苯基脲唑 | CAS号103-71-9 异氰酸苯酯 | CAS号17696-94-5 2-[(苯基氨基)羰基]-肼羧酸乙酯 | CAS号1207170-30-6 1-(2-hydroxy-5-... | CAS号2693-32-5 2-diphenylmethy... | CAS号1330068-60-4 9-methyl-14-phe... | CAS号32494-23-8 3,7-diphenyl-1,... | CAS号103-71-9 异氰酸苯酯 | CAS号700-58-3 2-金刚烷酮 | CAS号15988-11-1 4-苯基脲唑 | CAS号102-07-8 |N|,|N|'-二苯基脲 | CAS号63376-35-2 3,5-dioxo-N,4-d... | CAS号3422-01-3 苯基氨基甲酸叔丁酯

合成工艺路线路线简述

    2-[(苯基氨基)羰基]-肼羧酸乙酯置于氢氧化钾 Dinitrogen Tetraoxide,Sodium Sulfate体系中,用 二氯甲烷,水 作为反应溶剂,化学反应 2.0H,反应生成 4-苯基-1,2,4-三唑啉-3,5-二酮
    参考文献:1,2,4-三唑啉-3,5-二酮与双环烯烃的环加成反应导致重排乌唑的机理
    标题:1,2,4-三唑啉-3,5-二酮与双环烯烃的环加成反应导致重排乌唑的机理
    摘要:Mise En Evidence De L'Intervention D'Un Ion Aziridinium Dans La形成 Du Cycle Urazole Transpose Au Cours De La Cycloaddition Des Triazolinediones Avec Le Benzonorbornadiene,Les Norbornenes Et Des Bicycloalcenes尖
    DOI:10.1021/ja00322A023

    海关参考信息

    专利信息


    专利号:US-2022267266-A1
    优先权日:2019-07-09
    标 题 :Improved, cost effective process for synthesis of vitamin d3 and its analogue calcifediol from ergosterol
    发明人:DATLA ANUPAMA; NAGRE PRASHANT; TAMORE JAGDISH; PRABHU MANOJKUMAR SADANAND; KADAM SACHIN VASANT
    权利人:FERMENTA BIOTECH LTD
    摘要:Disclosed herein is an improved and efficient process for synthesis of vitamin D3 and its analogue Calcifediol from Ergosterol. Particularly, the present invention discloses the synthesis of key intermediate 3β-tert-Butyldimethylsilyloxy-22-hydroxy-23,24-bisnorchola-5,7-diene (5), and novel intermediate β-tert-Butyldimethylsilyloxy-22-iodo-23,24-bisnorchola-5,7-diene (9) by a simple and cost effective process. The industrially viable processes for preparation of said intermediate(s) results in providing provitamins with various side chains and the desired products in high yield.

    专利号:WO-9847910-A1
    优先权日:1997-04-21
    标题:Method for solution phase synthesis of oligonucleotides
    发明人:PIEKEN WOLFGANG; MCGEE DANNY; SETTLE ALECIA; ZHAI YANSHENG; HUANG JIANPING; HILL KEN; SMITH RANDALL S
    权利人:NEXSTAR PHARMACEUTICALS INC; PIEKEN WOLFGANG; MCGEE DANNY; SETTLE ALECIA; ZHAI YANSHENG; HUANG JIANPING; HILL KEN; SMITH RANDALL S
    摘要:This invention discloses an improved method for the sequential solution phase synthesis of oligonucleotides. The method lends itself to automation and is ideally suited for large scale manufacture oligonucleotides with high efficiency.

    专利号:US-4287129-A
    优先权日:1980-07-28
    标 题:Synthesis of 1α-hydroxy-7-dehydrosteroids
    发明人:KLAUSMEIER WILLIAM H; JOHNSON RICHARD L; HIRSCH ARNOLD L
    权利人:DIAMOND SHAMROCK CORP
    摘要:Enol acetylation is carried out on a variety of 1,4,6-trien-3-ones to form 1,3,5,7 tetraene structures from which 1 alpha -hydroxy-7-dehydro steroids are obtained. The compounds are intermediates used in the preparation of vitamin D3 metabolites such as 1 alpha ,25-dihydroxyvitamin D3 and 1 alpha -hydroxyvitamin D3.

    专利号:US-5087709-A
    优先权日:1988-04-11
    标 题 :Process for the preparation of 1α,25-dihydroxyvitamin D2 and the 24-epimer thereof
    发明人:TSUJI MASAHIRO; YOKOYAMA SHINJI; TACHIBANA YOJI
    权利人:NISSHIN FLOUR MILLING CO
    摘要:(22E)-5,7,22-Ergostatriene-1α,3β,25-triol and the 24-epimer thereof which are new intermediates for the synthesis of 1α,25-dihydroxyvitamin D 2 and the 24-epimer thereof. A new process for the preparation of 1α,25-dihydroxyvitamin D 2 and the 24-epimer thereof is also described which comprises irradiation of (22E)-5,7,22-ergostatriene-1α,3β,25-triol or the 24-epimer thereof followed by isomerization.

    专利号:US-6399767-B1
    优先权日:1996-09-03
    标 题 :Intermediates for the synthesis of vitamin D and steroid derivatives and process for preparation thereof
    发明人:HORNE DAVID A; KUBODERA NOBORU; SUZUKI HIROSHI; SHIMIZU HITOSHI
    权利人:UNIV COLUMBIA; CHUGAI PHARMACEUTICAL CO LTD
    摘要:A process for preparing a compound having structure (I) wherein n is an integer from 1-5; each of R 1 and R 2 independently is optionally substituted C 1 -C 6 alkyl; each of W and X is independently hydrogen or C 1 -C 6 alkyl; Y is O, S or NR 3 where R 3 is hydrogen, C 1 -C 6 alkyl or a protective group; and Z is a CD ring structure, a steroid structure, or a vitamin D structure, each of which optionally having structure (IV) wherein W, X, Y and Z are defined above, in the presence of a base, with a compound having structure (V) or (v′) wherein n, R 1 and R 2 are as defined above, and E is an eliminating group.

    专利号:US-9212137-B2
    优先权日:2012-05-30
    标题:Crystallization of (20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3 and related precursors
    发明人:DELUCA HECTOR F; GRZYWACZ PAWEL; PLUM LORI A; FLORES AGNIESZKA; THODEN JAMES B; HOLDEN HAZEL M
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:Disclosed are methods of purifying the compound (20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D 3 to obtain the compound in crystalline form. The methods typically include the steps of dissolving a product containing the compound in a solvent comprising hexane and 2-propanol, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals. Certain diol precursors formed during the synthesis of the compound and its diasteromers also may be obtained in crystalline form using ethyl acetate as a solvent.
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    主要参考文献

    [参考文献]: Jiri Adamec, Et Al. Development And Optimization Of An Lc-Ms/ms-Based Method For Simultaneous Quantification Of Vitamin D2 , Vitamin D3 , 25-Hydroxyvitamin D2 And 25-Hydroxyvitamin D3. J Sep Sci. 2011 Jan;34(1):11-20.

    合成参考文献


    摘要:Collier, S. J.; Singh, S. K., Science of Synthesis, (2010) 45, 49.
    摘要:Diver, S. T., Science of Synthesis, (2009) 46, 131.
    摘要:Krishnamoorthy, R., Science of Synthesis Knowledge Updates, (2013) 1, 412.
    摘要:Fringuelli, F.; Piermatti, O., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 505.
    摘要:Elliott, M. C.; Jones, D. H., Science of Synthesis: Multicomponent Reactions, (2013) 2, 246.
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