Se-phenyl 2-chlorobenzenecarboselenoate | 62247-17-0

• 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: Se-phenyl 2-chlorobenzenecarboselenoate
• 英文别名: 2-Chlor-monoselenobenzoesaeure-Se-phenylester；Se-phenyl 2-chlorobenzoselenoate；Se-phenyl 2-chlorobenzeneselenoate；2-chlorobenzenecarboselenoic acid Se-phenyl ester
• CAS: 62247-17-0
• 化学式: C₁₃H₉ClOSe
• 分子量: 295.627
• InChiKey: MHWPISLUJYYBRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-碘萘 、 Se-phenyl 2-chlorobenzenecarboselenoate 在 三(2-呋喃基)膦 、 norbornene 、 potassium carbonate 、 palladium dichloride 作用下， 反应 16.0h， 以91%的产率得到(2-chlorophenyl)(1-(phenylselanyl)naphthalen-2-yl)methanone
  参考文献：
  名称：

  Palladium/Norbornene-Catalyzed Ortho-Acylation and Ipso-Selenation via C(O)–Se Bond Cleavage: Synthesis of α-Carbonyl Selane

  摘要：

  A palladium/norbornene-catalyzed synthetic method that combines selective ortho C-H bond activation with sequential reactions to form complex selenide compounds has been developed. The C(O)-Se bond in selenoates is successfully cleaved, and various kinds of alpha-carbonyl selanes were synthesized in decent to excellent yields. The reaction has good functional group tolerance and broad substrate scope.

  DOI：

  10.1021/acs.orglett.8b00112
• 作为产物：
  描述：

  2-氯苯甲酸 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 乙酸乙酯 为溶剂， 反应 17.17h， 生成 Se-phenyl 2-chlorobenzenecarboselenoate
  参考文献：
  名称：

  由酸酐进行的苯甲硒酸酯的一般，轻度和无金属合成及其在肽合成中的用途

  摘要：

  开发了一种温和，实用和简单的方法，用于从几种酸酐和二苯基二硒化物合成苯基硒酸酯。这种无过渡金属的方法可以直接进入可存储的Fmoc-氨基酸硒酸酯，它们是有效的化学选择性酰化试剂。说明了在寡肽合成中的应用。

  DOI：

  10.1021/acs.joc.7b00173

文献信息

• Synthesis of selenol esters from diorganyl diselenides and acyl chlorides under solvent-free conditions and microwave irradiation
  作者：Marcelo Godoi、Eduardo W. Ricardo、Giancarlo V. Botteselle、Fabio Z. Galetto、Juliano B. Azeredo、Antonio L. Braga

  DOI：10.1039/c1gc16243h

  日期：——

  Herein, we report an efficient, quick and eco-friendly new method for the synthesis of a variety of selenol esters. This novel solvent-free methodology gave good to excellent isolated yields of desired products after just 2 min under microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize selenocarbonates bearing interesting functionalities.

  在此，我们报告了一种高效，快速且生态友好的合成多种硒醇的新方法 酯类。这本小说溶剂在微波辐射下仅2分钟后，无溶剂方法获得了所需产品的优异分离收率。此外，通过使用相同的绿色方法，我们还能够合成具有有趣功能的硒代碳酸盐。
• Efficient synthesis of selenoesters from acyl chlorides mediated by CuO nanopowder in ionic liquid
  作者：Devender Singh、Senthil Narayanaperumal、Kashif Gul、Marcelo Godoi、Oscar Endrigo Dorneles Rodrigues、Antonio Luiz Braga

  DOI：10.1039/c002648d

  日期：——

  Herein, we report an eco-friendly synthesis of selenoesters from acyl chlorides catalyzed by recyclable CuO nanopowder in ionic liquid as a recyclable solvent in good to excellent yields. This protocol shows high efficiency in catalyzing this transformation in a greener fashion than previous protocols due to the non-residual methodological design.

  本文报道了一种环保的合成硒酯方法，通过在可回收的离子液体中，以可回收的CuO纳米粉末作为催化剂，从酰氯合成硒酯，产率良好至卓越。该方法由于采用了无残留的工艺设计，在催化这一转化过程中比以往的方案更高效且更环保。
• Efficient synthesis of selenol esters from acid chlorides mediated by indium metal
  作者：Graciane Marin、Antonio L. Braga、Anderson S. Rosa、Fábio Z. Galetto、Robert A. Burrow、Hugo Gallardo、Marcio W. Paixão

  DOI：10.1016/j.tet.2009.03.069

  日期：2009.6

  This article describes an efficient and easy one-pot route for the synthesis of a wide range of selenol esters from acyl chloride with diselenides in the presence of indium metal. A variety of functional groups can be tolerated within the diorgano diselenide and the acyl chloride coupling partner.

  本文介绍了一种在铟金属存在下，由酰氯与二硒化物合成多种硒醇酯的有效且简便的一锅法。在二有机二硒化物和酰氯偶联伴侣中可以容忍多种官能团。
• Green synthesis and antibacterial activity of chalcogenoesters
  作者：Rafael S. da Silva、Guerino B. Junior、Letiére C. Soares、Fernanda H. da Rosa、Bruno B. Ravanello、Luciano Dornelles、Victor dos S. Barboza、Rodrigo de A. Vaucher、Roberto C. V. Santos、Bernardo Baldisserotto、Oscar E. D. Rodrigues

  DOI：10.1007/s00706-020-02565-x

  日期：2020.3

  methodology for the synthesis of chalcogenoester in good-to-excellent yields in a short time, with an easy work-up/purification step, and in a greenest methodology, affording the minimum generation of solid and liquid waste, in comparison to that described in the literature. Additionally, some selected compounds were evaluated as antimicrobial agents, showing moderate activity against a variety of

  摘要在此，我们提出了一种新的生态友好方法，可在短时间内以良好至优异的产率合成硫属元素酸酯，并且易于后处理/纯化步骤，并且采用最绿色的方法，生成的硫最少与文献中描述的相比，固废和废液的排放量更高。此外，某些选定的化合物被评估为抗微生物剂，对各种微生物（包括肺炎克雷伯菌，铜绿假单胞菌和某些选定的鱼类致病菌）表现出中等活性。 图形摘要
• Iron-Catalyzed Synthesis of Selenoesters from Diselenides and Acyl Chlorides or Acid Anhydrides in the Presence of Magnesium Dust
  作者：Lei Wang、Kai Ren、Min Wang、Ping Liu

  DOI：10.1055/s-0029-1219229

  日期：2010.4

  for the iron-catalyzed preparation of selenoesters by the reaction of diselenides with acyl chlorides or acid anhydrides has been developed. In the presence of magnesium dust, iron catalyzes the cleavage of the Se-Se bonds of the diselenides; the subsequent smooth reaction with acyl chlorides or acid anhydrides generates the corresponding selenoesters in good yields. The reaction could be carried out

  通过二硒化物与酰氯或酸酐的反应，铁催化制备硒酸酯的新型有效合成方法已得到开发。在镁尘的存在下，铁催化二硒化物的Se-Se键断裂；随后与酰氯或酸酐进行的平滑反应可产生相应的硒酸酯，收率很高。该反应可以在中性反应条件下进行，该方法简单，高效，实用。 铁催化剂-镁尘-硒酸酯-二硒化物-酰氯-酸酐