2-(phenylsulfonyl)-2-propenyl alcohol | 63068-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(phenylsulfonyl)-2-propenyl alcohol
• 英文别名: 2-(Benzenesulfonyl)-2-propen-1-ol；2-(phenylsulfonyl)-2-propen-1-ol；2-benzenesulfonyl-prop-2-en-1-ol；2-(phenylsulfonyl)-2-propene-1-ol；2-(Phenylsulfonyl)prop-2-en-1-ol；2-(benzenesulfonyl)prop-2-en-1-ol
• CAS: 63068-00-8
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: BVCVNTFTAHNUTB-UHFFFAOYSA-N

物化性质

• 沸点：
  406.2±37.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(phenylsulfonyl)-2-propenyl alcohol 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 0.08h， 生成 N-(2-(苯基磺酰基)-2-丙烯基)哌啶
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  2-(phenylthio)prop-2-en-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以4.30 g (72%)的产率得到2-(phenylsulfonyl)-2-propenyl alcohol
  参考文献：
  名称：

  Reagents for rapid peptide synthesis

  摘要：

  本发明涉及以下结构的化合物：##STR1## 其中R是一个电子吸引基团；R.sub.1是H或COZ；X.sub.1和X.sub.2独立地是H、较低的烷基、芳基、芳基较低烷基或聚苯乙烯，或者R和X.sub.1与它们附着的碳原子一起形成一个含有4到15个环碳原子并且可能含有最多2个杂原子的环，其中杂原子是O、S或N；Z是氨基酸残基、肽残基或离去基团。本发明的化合物可用作肽合成中有用的胺组成部分的阻断或保护基团。本发明还涉及在修改分子的除受保护的氨基团之外的部分时保护有机分子的氨基团的方法。

  公开号：

  US05221754A1

文献信息

• Facile 1,3-diaza-Claisen Rearrangements of Tertiary Allylic Amines Bearing an Electron-Deficient Alkene
  作者：Rachel M. Aranha、Amy M. Bowser、Jose S. Madalengoitia

  DOI：10.1021/ol802577z

  日期：2009.2.5

  Tertiary allylic amines with an electron-deficient alkene react with isocyanates and isothiocyanates to give highly substituted ureas and thioureas arising from formal 1,3-diaza-Claisen rearrangements. Isocyanates and isothiocyanates with strong electron-withdrawing groups are more reactive. Similarly, the data suggest that a stronger electron-withdrawing substituent on the alkene favors a faster reaction

  具有电子欠缺烯烃的叔烯丙基胺与异氰酸酯和异硫氰酸酯反应，生成由正规的1,3-二氮杂-克莱森重排产生的高度取代的脲和硫脲。具有强吸电子基团的异氰酸酯和异硫氰酸酯更具反应性。类似地，数据表明，烯烃上更强的吸电子取代基有利于更快的反应，但是这可以被环状过渡态的空间位阻所抵消。
• Identification of 4-Substituted 1,2,3-Triazoles as Novel Oxazolidinone Antibacterial Agents with Reduced Activity against Monoamine Oxidase A
  作者：Folkert Reck、Fei Zhou、Marc Girardot、Gunther Kern、Charles J. Eyermann、Neil J. Hales、Rona R. Ramsay、Michael B. Gravestock

  DOI：10.1021/jm0400810

  日期：2005.1.1

  Oxazolidinones represent a new and promising class of antibacterial agents. Current research in this area is mainly concentrated on improving the safety profile and the antibacterial spectrum. Many oxazolidinones, including linezolid (marketed as Zyvox), are inhibitors of monoamine oxidase A (MAO-A), which presents an undesired side effect. Recently, it was found that the 1,2,3-triazole is a good replacement

  恶唑烷酮代表一类新的有希望的抗菌剂。目前在该领域的研究主要集中在改善安全性和抗菌谱上。许多恶唑烷酮，包括利奈唑胺（以Zyvox销售），都是单胺氧化酶A（MAO-A）的抑制剂，具有不良的副作用。最近，发现1,2,3-三唑是恶唑烷酮中常规乙酰胺官能团的良好替代品。我们现在公开的发现是，在4位上带有取代基（如甲基，小取代的甲基，溴或线性（sp杂化）基团）的1,2,3-三唑（化合物如5、16、19和21 ）是在检测限内对MAO-A活性降低或没有活性的良好抗菌剂。该结果对于开发具有改善的安全性的恶唑烷酮特别有希望。可以在对接至MAO-A / MAO-B同源性模型的基础上合理化MAO-A SAR。
• A solid-phase version of the palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2
  作者：Lydia Carde、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/s0040-4039(01)00434-8

  日期：2001.5

  A solid-phase version of the palladium-catalyzed carbonyl allylation of aldehydes by allylic alcohols is described. Preliminary studies have been carried out with resin bound aldehydes 1a–c and different allylic alcohols. Solvent effects as well as the regio- and diastereoselectivity of our solid-phase conditions are compared with solution-phase protocols.

  描述了通过烯丙基醇的钯催化的醛的羰基烯丙基化的固相形式。已经对树脂结合的醛1a – c和不同的烯丙醇进行了初步研究。我们将固相条件下的溶剂效应以及区域和非对映选择性与溶液相方案进行了比较。
• [EN] OXAZOLIDINONE DERIVATIVES, PROCESSES FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] COMPOSES CHIMIQUES
  申请人：——

  公开号：WO2003072576A3

  公开（公告）日：2003-12-31
• Synthesis and reactions of .alpha.-methylene-.beta.-keto sulfones
  作者：Andreas Weichert、H. Martin R. Hoffmann

  DOI：10.1021/jo00013a007

  日期：1991.6

  Modified Jones oxidation of 2-(benzenesulfonyl)-2-alken-1-ols and rapid nonnucleophilic workup below 0-degrees-C yields a variety of alpha-methylene-beta-keto sulfones 4, including crystalline parent 4a and also e-h, which can be stored at -20-degrees-C without change. In the absence of nucleophiles, the new compounds are stable (heating in benzene) toward dimerization and polymerization. Thus, selective cross-reactions are feasible. With alcohols, including sterically hindered tertiary alcohols and also with 2-(ethoxycarbonyl)cyclopentanone, the compounds function as efficient Micheal acceptors, even in the absence of base catalysis. In moist ether, 2-(benzenesulfonyl)-1-penten-3-one (4b) suffers rearrangement to 2-(benzenesulfonyl)ethyl propanoate (9). Sulfonylated alcohol 7 and strained alpha-hydroxyoxetane 8 are assumed as intermediates. Toward electron-rich aromatics and heteroaromatics, alpha-methylene-beta-keto sulfones 4 behave as electrophiles in Friedel-Crafts-type functionalizations. The new compounds are also dienophilic: of the two groups (acetyl and benzenesulfonyl) attached to the ethylenic terminus in 4a, benzenesulfonyl has been found to preferentially adopt the endo position in cycloadditions of cyclopentadiene and also cyclohexadiene. Prototype 3-(benzenesulfonyl)-3-buten-2-one (4a) is a crystalline methyl vinyl ketone (MVK) equivalent which, unlike MVK, undergoes controlled free-radical additions with nucleophilic radicals. In hetero-Diels-Alder reactions, 4a serves as a 1-oxa-1,3-butadiene unit, combining with a wide range of alkenes of graded nucleophilicity. Electron deficient 4a also reacts as an enophile toward 1,1-dialkylated ethylenes. In the presence of ZnCl2.OEt2, the ene reaction with beta-piene can be suppressed completely in favor of cycloaddition, giving a robustadial building block in 85% yield. In further applications to natural products chemistry, the synthesis of frontalin and novel oxatricyclics are described.

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