benzyl (phenylseleno)formate

• 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: benzyl (phenylseleno)formate
• 英文别名: O-benzyl Se-phenyl carbonoselenoate；benzyl phenylselanylformate
• 化学式: C₁₄H₁₂O₂Se
• 分子量: 291.208
• InChiKey: IJBFNHSBTXGMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘萘 、 benzyl (phenylseleno)formate 在 三(2-呋喃基)膦 、 norbornene 、 potassium carbonate 、 palladium dichloride 作用下， 反应 16.0h， 以63%的产率得到benzyl 1-(phenylselanyl)-2-naphthoate
  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：

  二苯基二硒醚 、 氯甲酸苄酯 在 锌 作用下， 反应 0.03h， 以62%的产率得到benzyl (phenylseleno)formate
  参考文献：
  名称：

  硒醇的合成 酯类 来自二有机基 二硒 和 酰氯 在下面 溶剂无条件和微波辐射

  摘要：

  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。

  DOI：

  10.1039/c1gc16243h

文献信息

• 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。
• On water preparation of phenylselenoesters
  作者：Claudio Santi、Benedetta Battistelli、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1039/c2gc16541d

  日期：——

  PhSeZn-halides react under “on water” mild conditions with acid chlorides to provide a high yield route to a variety of aromatic and aliphatic phenylselenoesters.

  PhSeZn-卤化物在“水上”温和条件下与酰氯反应，为多种芳香族和脂肪族苯基硒酯提供高产率途径。
• (Aryltelluro)formates as Precursors of Alkyl Radicals:  Thermolysis and Photolysis of Primary and Secondary Alkyl (Aryltelluro)formates
  作者：Mathew A. Lucas、Carl H. Schiesser

  DOI：10.1021/jo960838y

  日期：1996.1.1

  Alkyl (aryltelluro)formates are effective precursors of oxyacyl, methyl, and primary and secondary alkyl radicals. At room temperature, irradiation of a benzene solution of methyl (aryltelluro)formates 10-12, 2-methylpropyl (aryltelluro)formates 14 and 15, octyl (phenyltelluro)formate (17), cyclohexyl (aryltelluro)formates 19 and 20, 3 beta-cholestanyl (aryltelluro)formates 22 and 23, cholesteryl (phenyltelluro)formate (24) and benzyl (phenyltelluro)formate (27) with a 250-W low-pressure mercury lamp leads to the formation of oxyacyl radicals (34), which can be trapped by diphenyl diselenide to give the corresponding alkyl (phenylseleno)formates 13, 16, 18, 21, 24, 26, and 28 with excellent overall conversions. Thermolysis of these telluroformates at 160 degrees C in the dark leads to the formation of methyl and primary and secondary alkyl aryl tellurides 36-43 in excellent yields. Presumably, these transformations involve oxyacyl radicals, which undergo subsequent decarboxylation at the elevated temperature to afford alkyl radicals, which become involved in further radical chemistry. When 1-(benzylseleno)-5-hexyl (phenyltelluro)formate (44) was thermolysed under these conditions, 2-methylselenane (45) was observed as the sole selenium-containing product, demonstrating the synthetic utility of (aryltelluro)formates as alkyl radical precursors.
• Zn in ionic liquid: an efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters
  作者：Senthil Narayanaperumal、Eduardo E. Alberto、Kashif Gul、Cristiane Yuriko Kawasoko、Luciano Dornelles、Oscar E.D. Rodrigues、Antonio Luiz Braga

  DOI：10.1016/j.tet.2011.04.018

  日期：2011.6

  A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents. (C) 2011 Elsevier Ltd. All rights reserved.