1-phenylethyl phenyl selenide | 39192-26-2

• 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: 1-phenylethyl phenyl selenide
• 英文别名: phenyl(1-phenylethyl)selane；<1-(phenylseleno)ethyl>benzene；α-Methylbenzyl-phenylselenid；[(1-Phenylethyl)selanyl]benzene；1-phenylethylselanylbenzene
• CAS: 39192-26-2
• 化学式: C₁₄H₁₄Se
• 分子量: 261.225
• InChiKey: ZCRATCBAGPGPJL-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-phenylethyl phenyl selenide 在 三苯基氢化锡 作用下， 反应 2.5h， 以73%的产率得到乙基苯
  参考文献：
  名称：

  Organic tellurium and selenium chemistry. Reduction of tellurides, selenides, and selenoacetals with triphenyltin hydride

  摘要：

  DOI：

  10.1021/ja00533a024
• 作为产物：
  描述：

  sodium phenylselenide 在 lithium diisopropyl amide 作用下， 以 乙醇 、 苯 为溶剂， 反应 2.17h， 生成 1-phenylethyl phenyl selenide
  参考文献：
  名称：

  Mitchell, Reginald H., Canadian Journal of Chemistry, 1980, vol. 58, p. 1398 - 1406

  摘要：

  DOI：

文献信息

• Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
  作者：Fuhai Li、Dan Wang、Hongyi Chen、Ze He、Lihong Zhou、Qingle Zeng

  DOI：10.1039/d0cc05633b

  日期：——

  A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72–94%). Using quaternary ammonium salts

  开发了一种新的方案，以从（手性）苄基三甲基铵盐和二（杂）芳基二硫化物或二硒化物合成（对映体富集）硫醚和硒醚。弱碱的存在促进了这些合成，并且不需要使用任何过渡金属，从而使目标产物的收率达到了良好或优异（72-94％）。使用由对映体富集的胺合成的季铵盐可生成高度对映纯的苄基硫醚和硒醚（94-99％ee），其构型与对映体富集的季铵盐相反。
• A Facile Method for Synthesis of Alkyl Phenyl Selenides. The Reaction of Diphenyl Diselenide with Oxygen-containing Compounds Using La/Me₃SiCl/^cat.I₂/^cat.CuI System
  作者：Toshiki Nishino、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1246/cl.2003.918

  日期：2003.10

  Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me3SiCl/cat.I2/cat.CuI. It was suggested that alkyl phenyl selenides were formed by the SH2 type reaction of diphenyl diselenide with alkyl radicals generated from alcohols, ethers or esters.

  通过二苯基二硒化物和 La/Me3SiCl/cat.I2/cat.CuI 的反应，醇、醚和酯直接转化为相应的烷基苯基硒化物。有人提出烷基苯基硒化物是由二苯基二硒化物与醇、醚或酯产生的烷基自由基的SH2型反应形成的。
• Novel synthesis of tertiary alkyl, secondary and tertiary benzyl, and allyl selenides from the corresponding alcohols
  作者：M. Clarembeau、A. Krief

  DOI：10.1016/s0040-4039(01)91092-5

  日期：1984.1

  We report an efficient synthesis of the title compounds from alcohols and selenols. The scope and limitations of the new method are disclosed.

  我们报告了从醇和硒醇的标题化合物的有效合成。公开了新方法的范围和局限性。
• A novel regioselective reaction of styrene with magnesium organoselenolates to afford unsymmetrical selenides catalyzed by CuI and l-proline
  作者：Fei Gao、Yu Tang、Zhi-hao Li、Feng Pan、Jun Yang、Yuan-ming Zhang

  DOI：10.1016/j.tetlet.2012.08.046

  日期：2012.10

  A novel regioselective reaction of styrene with the prepared magnesium organoselenolates from magnesium, alkyl or aryl bromides, and selenium has been developed in one pot. The reaction catalyzed by CuI and l-proline proceeded in THF, water, and toluene. The scope and limitations of this reaction have been examined. The reaction afforded unsymmetrical selenides containing 12 new compounds in good to

  在一锅中开发了苯乙烯与由镁，烷基或芳基溴化物和硒制得的有机硒化镁的新型区域选择性反应。由CuI和1-脯氨酸催化的反应在THF，水和甲苯中进行。已经检查了该反应的范围和局限性。该反应以高至高收率提供了包含12种新化合物的不对称硒化物。
• Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: a straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
  作者：Subhash Banerjee、Laksmikanta Adak、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2012.02.047

  日期：2012.4

  A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing ‘in situ’ generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated

  使用离子液体/三苯基膦（PPh 3）和便捷的方案，通过“原位”生成的硫醇盐或硒酸根离子缩合一锅合成不对称的硫化物和硒化物，已实现了对二苯基二硫化物和二苯基二硒化物的无金属裂解。已经开发出具有卤代烷的化合物。此外，还证明了将生成的硫醇盐阴离子与1，4-共轭加成到活化烯烃上。离子液体溴化1-甲基-3-戊基咪唑鎓[pmIm] Br在促进反应过程中起着至关重要的作用，并且与其他溶剂相比，具有出色的活性和选择性。[pmIm] Br已被重复使用至少五次而没有明显的活性损失。