benzenecarboselenoic acid Se-benzyl ester | 63147-16-0

• 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: benzenecarboselenoic acid Se-benzyl ester
• 英文别名: Benzyl benzenecarboselenoate；Se-Benzyl benzeneselenoate；Se-benzyl benzoselenoate；Se-benzyl selenobenzoate；selenobenzoic acid Se-benzyl ester；Selenobenzoesaeure-Se-benzylester；Se-benzyl benzenecarboselenoate
• CAS: 63147-16-0
• 化学式: C₁₄H₁₂OSe
• 分子量: 275.209
• InChiKey: KMOXIGLXNMJDSN-UHFFFAOYSA-N

物化性质

• 沸点：
  389.4±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  benzenecarboselenoic acid Se-benzyl ester 在 碘 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以88%的产率得到二苄基二硒醚
  参考文献：
  名称：

  在甲醇溶液中存在元素碘的情况下，硒醇酯高效一步转化为对称二硒化物

  摘要：

  已经开发了一种简便、有效和方便的方法，用于在室温下在元素碘的存在下将硒醇酯直接转化为相应的二硒化物。

  DOI：

  10.1080/10426500902753379
• 作为产物：
  描述：

  selenobenzamide 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 benzenecarboselenoic acid Se-benzyl ester
  参考文献：
  名称：

  A Novel Synthesis of Selenides and Selenol Esters Using Liquid-Liquid Phase-Transfer Catalysis

  摘要：

  This article describes the first attempt to synthesize selenides and selenol esters prepared from the reaction of 1-benzyl or 1-acylselenophenylmethaniminium halides and organic halides under liquid-liquid phase-transfer conditions. This method also can be applied to the synthesis of diseleno tweezers-like molecules as metalloreceptors.

  DOI：

  10.1080/10426500307940

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。
• Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature
  作者：Rana Chatterjee、Anindita Mukherjee、Sougata Santra、Grigory V. Zyryanov、Adinath Majee

  DOI：10.1016/j.tet.2019.130624

  日期：2019.10

  An Fe(III)-catalyzed efficient method has been developed for the synthesis of selenoester derivatives in high yields through the coupling of α-amino carbonyl/glycine derivatives and diselenides under ambient air. A library of benzoselenoate derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. Experimental results suggest that the reaction

  已经开发了一种Fe（III）催化的有效方法，可通过在环境空气下将α-氨基羰基/甘氨酸衍生物与二硒化物偶联来以高收率合成硒酸酯衍生物。已经合成了具有多种取代基的苯并硒酸酯衍生物的文库。已经预测到可能的反应途径。实验结果表明该反应通过自由基途径进行。操作简便，与各种α-氨基羰基和二硒化物的相容性，高收率，快速反应和温和的反应条件是该方法的显着优势。我们还显示了合成的硒酸酯的实际应用，其可用于在生物科学中产生肽键。
• 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。
• Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis(1,5-cyclooctanediylboryl) Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Michiko Kawaguchi、Kumiko Dobashi、Yumi Nagano、Manabu Fujimura、Eiichi Kudoh、Tomonari Kai、Noboru Saito、Jun-ichi Masuda、Masaki Iwaya、Hiroyuki Fujisawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.70.197

  日期：1997.1

  Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis(1,5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2,3-dimethyl-1,3-butadiene to give the corresponding [4+2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding selenoamides, a selenoester, and sterically protected selones, respectively, in modest yields. On the other hand, a similar treatment of cinnamaldehyde with the reagent gave the 2,3-dihydroselenophene derivative, which originated from a [4+2]-type self-dimerization of in situ generated 3-phenyl-2-propeneselenal.

  在原位生成硒醛和硒酮，通过将醛或酮与双(1,5-环辛烷二基)硒化物处理；由此得到的硒羰基化合物与2,3-二甲基-1,3-丁二烯反应，形成相应的[4+2]环加成物。将具有体积较大取代基的酰胺、酯和酮与该试剂处理，亦分别得到相应的硒酰胺、硒酯和体积保护的硒酮，产率适中。另一方面，将肉桂醛与该试剂处理，得到2,3-二氢硒苯衍生物，这源于原位生成的3-苯基-2-丙烯硒醛的[4+2]型自聚合反应。
• SYNTHESIS OF SELENOL ESTERS USING ACYL HALIDES AND A NOVEL SELENATING REAGENT, LiAlHSeH
  作者：Mamoru Koketsu、Hiroshi Asada、Hideharu Ishihara

  DOI：10.1080/10426500490422254

  日期：2004.3.1

  Several selenol esters were synthesized by the reaction of acyl chlorides with LiAlHSeH then with alkyl halides in moderate to good yields.

  通过酰氯与 LiAlHSeH 然后与烷基卤反应以中等至良好的收率合成了几种硒醇酯。