phenyl(1-phenylethyl)selane | 1415088-77-5

• 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: phenyl(1-phenylethyl)selane
• 英文别名: (S)-phenyl(1-phenylethyl)selane；[(1S)-1-phenylethyl]selanylbenzene
• CAS: 1415088-77-5
• 化学式: C₁₄H₁₄Se
• 分子量: 261.225
• InChiKey: ZCRATCBAGPGPJL-LBPRGKRZSA-N

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

• 作为产物：
  描述：

  硒氰酸苯酯 在 sodium phosphite 、 三丁基膦 、 Thermobifida fusca recombinant phenylacetone monooxygenase 、 phosphite dehydrogenase 、 NADP+ 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 25.0h， 生成 phenyl(1-phenylethyl)selane
  参考文献：
  名称：

  Chemoenzymatic approaches to obtain chiral-centered selenium compounds

  摘要：

  The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.087

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。
• Stereospecific Nucleophilic Substitution of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Benzyne
  作者：Yang Gui、Shi-Kai Tian

  DOI：10.1021/acs.orglett.7b00365

  日期：2017.4.7

  A one-pot protocol has been developed for sequential benzyne activation and nucleophilic substitution of enantioenriched tertiary benzylic amines. In the presence of 2-(trimethylsilyl)phenyl triflate and CsF, a range of enantioenriched tertiary benzylic amines were substituted by various nucleophiles, delivering structurally diverse benzylic compounds in moderate to excellent yields with excellent

  已经开发了一种一锅法方案，用于顺序进行苯并炔活化和对映体富集的叔苄基胺的亲核取代。在2-（三甲基甲硅烷基）苯基三氟甲磺酸酯和CsF的存在下，一系列对映体富集的叔苄基胺被各种亲核试剂取代，以中等至优异的收率提供结构多样的苄基化合物，并具有出色的对映体纯度保留率。重要的是，这种操作简单的方案允许在无金属条件下形成具有优异对映体纯度的各种手性C–S，C–Se，CC和C–N键。
• Enantioselective Selenol-ene Using Rh-Hydride Catalysis
  作者：Hannah S. Slocumb、Shaozhen Nie、Vy M. Dong、Xiao-Hui Yang

  DOI：10.1021/jacs.2c08475

  日期：2022.10.12
• Chemoenzymatic approaches to obtain chiral-centered selenium compounds
  作者：Patrícia B. Brondani、Nathalie M.A.F. Guilmoto、Hanna M. Dudek、Marco W. Fraaije、Leandro H. Andrade

  DOI：10.1016/j.tet.2012.09.087

  日期：2012.12

  The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved. (C) 2012 Elsevier Ltd. All rights reserved.