叔丁基苯基碲化物 | 83817-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 叔丁基苯基碲化物
• 英文名称: tert-butyl phenyl telluride
• 英文别名: tert-butyl(phenyl)telluride；tert-butyl(phenyl)tellane；t-BuTePh；tert.-Butylphenyltellurid；Phenyl t-butyl telluride；tert-butyltellanylbenzene
• CAS: 83817-38-3
• 化学式: C₁₀H₁₄Te
• 分子量: 261.821
• InChiKey: DTINPPSXCAPLFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  叔丁基苯基碲化物 在 苯硫酚 作用下， 以 氘代苯 为溶剂， 反应 1.0h， 以100%的产率得到异丁烷
  参考文献：
  名称：

  Arylthiols as Highly Chemoselective and Environmentally Benign Radical Reducing Agents

  摘要：

  Arylthiols serve as excellent environmentally benign reducing agents for organotellurium, organostibine, and organobismuthine compounds under radical conditions. Both small molecules and macromolecules possessing these heteroatorn groups are reduced under moderate thermal conditions to give near quantitative yields in most cases. The reduction shows high chemoselectivity with respect to the heteroatorn compounds the reactivity decreases in the order alkylbismuthines, alkylstibines, and alkyltellurides, while simple alkyl iodides could not be reduced. Alkyltellurides are selectively reduced in the presence of alkyl iodides even when an excess amount of arylthiol is used. Furthermore, alkylstibines are also selectively reduced in the presence of alkyltellurides. Moreover, the reduction conditions are compatible with the presence of a variety of polar functional groups in the substrates, products, and solvents, which are not tolerant under ionic and metal-catalyzed conditions. Carbon-carbon bond formation is possible with use of the carbon-centered radicals that are generated. The results clearly reveal the synthetic utility of arylthiols in organic synthesis.

  DOI：

  10.1021/jo801200b
• 作为产物：
  描述：

  溴代叔丁烷 、 phenyltellurotrimethylsilane 以 乙腈 为溶剂， 反应 24.0h， 以36%的产率得到叔丁基苯基碲化物
  参考文献：
  名称：

  由有机卤化物和甲硅烷基碲化物合成有机碲化合物的新方法。极性溶剂和离去基团的显着影响

  摘要：

  碲化甲硅烷基与有机卤化物反应生成相应的有机碲化合物和卤化甲硅烷基酯，收率良好。在相同条件下，取代反应在极性溶剂（例如乙腈）中进行，但在非极性溶剂中则不会进行。离去基团也起着重要的作用，烷基溴的反应性最高，烷基氯的反应性较小，而烷基碘的反应性最低。在真空下除去挥发性甲硅烷基卤化物和溶剂后，获得了基本纯的有机碲化合物，可以直接用作碳正离子，碳负离子和以碳为中心的自由基的前体。

  DOI：

  10.1016/s0040-4039(01)00931-5

文献信息

• Phenyltellanyl Triflate (PhTeOTf) as a Powerful Tellurophilic Activator in the Friedel–Crafts Reaction
  作者：Takeshi Yamada、Eri Mishima、Kazuya Ueki、Shigeru Yamago

  DOI：10.1246/cl.2008.650

  日期：2008.6.5

  A powerful electrophilic activator for organotellurium compounds was developed. Phenyltellanyl triflate (PhTeOTf) prepared in situ from dibromophenyl(phenyltellanyl)telluride and AgOTf selectively activated various organotellurium compounds in the presence of aromatic compounds yielding the corresponding Friedel–Crafts reaction products. Polymer-end organotellurium compounds were also activated by PhTeOTf providing the corresponding end-functionalized polymers.

  开发了一种用于有机碲化合物的高效亲电活化剂。由二溴苯基(苯基碲基)碲化物和AgOTf原位制备的苯基碲基三氟甲磺酸盐（PhTeOTf）在芳香化合物的存在下选择性地活化了各种有机碲化合物，生成了相应的Friedel-Crafts反应产物。聚合物端基有机碲化合物也能被PhTeOTf活化，提供了相应的端基功能化聚合物。
• An alternative approach for the synthesis of aryl–alkyl tellurides: reaction of aryl iodides with metal alkyltellurolates promoted by CuI
  作者：Márcio S. Silva、João V. Comasseto

  DOI：10.1016/j.tet.2011.09.014

  日期：2011.11

  Aryl iodides react with metal organotellurolates in tetrahydrofuran/dimethylformamide in the presence of CuI (5 mol %) or CuI (5 mol %) and 1,10-phenanthroline (10 mol %) to afford the corresponding aryl–alkyl tellurides in good yields.

  在CuI（5 mol％）或CuI（5 mol％）和1,10-菲咯啉（10 mol％）存在下，芳基碘化物与金属有机碲酸盐在四氢呋喃/二甲基甲酰胺中反应，以高收率提供相应的芳基-烷基碲化物。
• Experimental and theoretical studies on formal σ-bond metathesis of silyl tellurides with alkyl halides
  作者：Shigeru Yamago、Kazunori Iida、Jun-ichi Yoshida

  DOI：10.1016/j.jorganchem.2006.05.066

  日期：2007.1

  Silyl tellurides reacted with alkyl halides under mild thermal conditions to give the corresponding alkyl tellurides and silylhalides in good to excellent yields. Substitution took place much faster in polar solvents, such as acetonitrile, than that in non-polar solvents. After removal of the volatile silyl halides and solvent under vacuum, the essentially pure divalent organotellurium compounds were

  甲硅烷基碲化物与烷基卤化物在温和的热条件下反应，以良好或优异的收率得到相应的烷基碲化物和甲硅烷基卤化物。在极性溶剂（如乙腈）中的取代要比在非极性溶剂中的取代快得多。在真空下除去挥发性甲硅烷基卤化物和溶剂后，获得了基本上纯的二价有机碲化合物。进行理论计算以了解反应机理，并获得了涉及四价有机碲中间体的逐步途径。由于中间体以及由反应物导致中间体的速率确定步骤具有高极性特征，因此它们将在极性溶剂中稳定。
• Arylthiols as Highly Chemoselective and Environmentally Benign Radical Reducing Agents
  作者：Shigeru Yamago、Atsushi Matsumoto

  DOI：10.1021/jo801200b

  日期：2008.9.19

  Arylthiols serve as excellent environmentally benign reducing agents for organotellurium, organostibine, and organobismuthine compounds under radical conditions. Both small molecules and macromolecules possessing these heteroatorn groups are reduced under moderate thermal conditions to give near quantitative yields in most cases. The reduction shows high chemoselectivity with respect to the heteroatorn compounds the reactivity decreases in the order alkylbismuthines, alkylstibines, and alkyltellurides, while simple alkyl iodides could not be reduced. Alkyltellurides are selectively reduced in the presence of alkyl iodides even when an excess amount of arylthiol is used. Furthermore, alkylstibines are also selectively reduced in the presence of alkyltellurides. Moreover, the reduction conditions are compatible with the presence of a variety of polar functional groups in the substrates, products, and solvents, which are not tolerant under ionic and metal-catalyzed conditions. Carbon-carbon bond formation is possible with use of the carbon-centered radicals that are generated. The results clearly reveal the synthetic utility of arylthiols in organic synthesis.
• A new, practical synthesis of organotellurium compounds from organic halides and silyl tellurides. Remarkable effects of polar solvents and leaving groups
  作者：Shigeru Yamago、Kazunori Iida、Jun-ichi Yoshida

  DOI：10.1016/s0040-4039(01)00931-5

  日期：2001.7

  Silyl tellurides react with organic halides to give the corresponding organotellurium compounds and silyl halides in good to excellent yields. Substitution proceeds in polar solvents, such as acetonitrile, but not in nonpolar solvents under identical conditions. The leaving group also plays a significant role, with alkyl bromides being the most reactive, alkyl chlorides less so and alkyl iodides the

  碲化甲硅烷基与有机卤化物反应生成相应的有机碲化合物和卤化甲硅烷基酯，收率良好。在相同条件下，取代反应在极性溶剂（例如乙腈）中进行，但在非极性溶剂中则不会进行。离去基团也起着重要的作用，烷基溴的反应性最高，烷基氯的反应性较小，而烷基碘的反应性最低。在真空下除去挥发性甲硅烷基卤化物和溶剂后，获得了基本纯的有机碲化合物，可以直接用作碳正离子，碳负离子和以碳为中心的自由基的前体。