(3-phenylpropyl)(trifluoromethyl)selane | 1519964-44-3

• 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: (3-phenylpropyl)(trifluoromethyl)selane
• 英文别名: 3-(Trifluoromethylselanyl)propylbenzene；3-(trifluoromethylselanyl)propylbenzene
• CAS: 1519964-44-3
• 化学式: C₁₀H₁₁F₃Se
• 分子量: 267.153
• InChiKey: OULFNNFEFBVAGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  1-溴-3-苯基丙烷 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (3-phenylpropyl)(trifluoromethyl)selane
  参考文献：
  名称：

  General Synthesis of Trifluoromethyl Selenides Utilizing Selenocyanates and Fluoroform

  摘要：

  Trifluoromethylated selenoethers are quite rare despite their potential and the interest that they generate. A series of trifluoromethylseleno derivatives, either primary and secondary aliphatic or aromatic and heterocyclic, is described herein by the reaction of easily prepared organic selenocyanates and CuCF3. Another beneficial feature of this reaction is the use of fluoroform as a source for the CF3 group, a compound whose chemistry is currently being intensively researched because it is a potent greenhouse gas that should not be released into the atmosphere.

  DOI：

  10.1021/jo5022844

文献信息

• Solvent free nucleophilic selenocyanation with [bmim][SeCN]. Direct access to perfluoroalkylselenide compounds
  作者：Arnaud De-Zordo Banliat、Kévin Grollier、Aurélie Damond、Thierry Billard、Guillaume Dagousset、Emmanuel Magnier、Bruce Pégot

  DOI：10.1016/j.tet.2021.132507

  日期：2021.11

  Available online-1-n-butyl-3-methylimidazolium selenocyanate ([bmim][SeCN]) proved to be a very efficient reagent for selenocyanation of alkyl halides. As part of an eco-friendly process, no organic solvents were used during the transformation and reaction times are reduced by using microwave as a heating source. The ionic liquid was carefully recycled in two different ways. Selenocyanate compounds

  在线提供的 1- n-丁基-3-甲基咪唑鎓硒氰酸盐 ([bmim][SeCN]) 被证明是一种非常有效的卤代烷硒氰化试剂。作为环保工艺的一部分，在转化过程中不使用有机溶剂，并通过使用微波作为加热源缩短了反应时间。离子液体以两种不同的方式小心地回收。硒氰酸酯化合物在一锅两步法中成功转化为三氟甲基硒化物。
• 一种醇的直接三氟甲硒基化方法
  申请人：武汉理工大学

  公开号：CN111018765B

  公开（公告）日：2020-12-22

  本发明公开了一种醇的直接三氟甲硒基化方法，其特征在于，包括以下步骤：在溶剂中加入三氟甲硒基盐和醇，在0℃至100℃下搅拌反应0.1～48h，加水淬灭，经柱层析分离纯化，得到三氟甲硒基化产品。本发明以三氟甲硒基盐和价格低廉的醇作为原料，在非常温和的反应条件下，无需添加过渡金属催化剂和配体，即可实现醇的三氟甲硒基化，为合成三氟甲基硒醚提供了一种新的高效、绿色的策略。本发明操作简单、条件温和、产率较高、官能团耐受性好，原料廉价易得，便于得到更多种类的三氟甲基硒醚。
• Synthesis of Cu^ITrifluoromethylselenates for Trifluoromethylselenolation of Aryl and Alkyl Halides
  作者：Chaohuang Chen、Li Ouyang、Quanfu Lin、Yanpin Liu、Chuanqi Hou、Yaofeng Yuan、Zhiqiang Weng

  DOI：10.1002/chem.201303934

  日期：2014.1.13

  copper(I) trifluoromethylselenolate reagents by the reaction of CuI with the Ruppert’s reagent (Me3SiCF3), KF, and elemental selenium in the presence of dinitrogen ligands in CH3CN at room temperature. The reagent [Cu(bpy)(SeCF3)]2 was proven to be air‐stable and highly efficient for nucleophilic trifluoromethylthselenolation of a broad range of (hetero)aryl halides and alkyl halides. This method represents

  合成三氟甲基硫醇盐化合物的新策略的开发在制药，农药和先进材料中具有相当重要的意义。因此，目前人们对开发有效的合成方法和试剂投入了很多注意力。相比之下，相当少的努力已经给予编制C的发展 SECF 3债券。本文中，我们报告了一条简明的路线，该路线是通过在室温下在CH 3 CN中存在二氮配体的情况下，CuI与Ruppert's试剂（Me 3 SiCF 3），KF和元素硒的反应来合成三氟甲基硒化铜（I）家族。温度。试剂[Cu（bpy）（SeCF 3）] 2被证明对多种（杂）芳基卤化物和烷基卤化物的亲核三氟甲基硫醚化反应具有空气稳定性和高效性。该方法代表了构建三氟甲基硒烯酸酯化合物的强大方法。
• Copper-Catalyzed Trifluoromethylselenolation of Aryl and Alkyl Halides: The Silver Effect in Transmetalation
  作者：Chaohuang Chen、Chuanqi Hou、Yuguang Wang、T. S. Andy Hor、Zhiqiang Weng

  DOI：10.1021/ol403406y

  日期：2014.1.17

  A catalytic trifluoromethylselenolation of aryl and alkyl halides by a Cu(I) catalyst has been developed. A key intermediate, [(phen)Cu(SeCF3)]2 (5) was successfully isolated and characterized by X-ray diffraction. The important role of silver in the transmetalation process during the catalytic cycle was elucidated. A wide range of trifluoromethylselanes have been prepared from readily available starting

  已经开发了通过Cu（I）催化剂催化芳基和烷基卤化物的三氟甲基硒化反应。关键中间体[（phen）Cu（SeCF 3）] 2（5）已成功分离，并通过X射线衍射进行了表征。阐明了银在催化循环过程中的过渡金属化过程中的重要作用。已经从容易获得的起始原料通过耐受各种重要官能团的方法制备了多种三氟甲基硒烷。
• CaCl₂-Promoted Dehydroxytrifluoromethylselenolation of Alcohols with [Me₄N][SeCF₃]
  作者：Shuai Wu、Tian-Hao Jiang、Cheng-Pan Zhang

  DOI：10.1021/acs.orglett.0c02109

  日期：2020.8.7

  A direct trifluoromethylselenolation of alcohols with the readily accessible [Me4N][SeCF3] salt has been reported. The reaction is significantly promoted by CaCl2 and proceeds smoothly through unprecedented carbonoselenoate intermediates to form the corresponding alkyl trifluoromethyl selenoethers in good yields. This protocol is also applicable to the late-stage dehydroxytrifluoromethylselenolation of complex alcohols owing to its mildness, good compatibility, high efficiency, and broad functional group tolerance.