[(Z)-2-(phenyltellanyl)vinyl]benzene | 82296-87-5

• 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: [(Z)-2-(phenyltellanyl)vinyl]benzene
• 英文别名: (Z)-1-phenyltelluro-2-phenylethene；(Z)-(styryl)(phenyl)telluride；(Z)-phenyl(styryl)telluride；(Z)-styryl phenyl telluride；[(Z)-2-phenylethenyl]tellanylbenzene
• CAS: 82296-87-5
• 化学式: C₁₄H₁₂Te
• 分子量: 307.849
• InChiKey: QDVQEUCCRDSNGV-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  [(Z)-2-(phenyltellanyl)vinyl]benzene 在 lithium tetrachloropalladate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以6%的产率得到(1Z,3Z)-1,4-diphenylbuta-1,3-diene
  参考文献：
  名称：

  Palladium-catalyzed homocoupling reactions of organic tellurides

  摘要：

  Organic tellurides containing a styryl moiety react in acetonitrile to give the corresponding homocoupling products, 1,3-dienes, with moderate to quantitative yields in the presence of a catalytic amount of Pd(OAc)(2) together with AgOAc at 25 degrees C. In contrast, such homocoupling reactions hardly occur with diaryl, alkyl aryl, dialkyl, and alkynyl aryl tellurides, even at reflux temperature and in the presence of a stoichiometric amount of palladium salt, in disagreement with reported results. The result of cross-over experiments suggests that this homocoupling reaction occurs between an alkenyl telluride and an alkenylpalladium species, the latter being formed via the migration of an alkenyl moiety from Te to Pd (transmetallation).

  DOI：

  10.1016/s0022-328x(96)06561-8
• 作为产物：
  描述：

  α-chloromethyl phenyl telluride 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.68h， 生成 [(Z)-2-(phenyltellanyl)vinyl]benzene
  参考文献：
  名称：

  A Simplified Preparation of Vinyl Sulfides, Selenides and Tellurides by a Wittig-Type Reaction

  摘要：

  描述了一种通过Wittig类型反应在一步法中制备几种乙烯基硫化物、硒化物和碲化物的方法。通过氯甲基酚类卤化物、叔丁氧化钾和三苯基磷的反应“原位”形成了硫族三苯基膦化合物3。化合物3与羰基化合物反应，得到优先为Z-构型的乙烯基硫族化合物6-9。

  DOI：

  10.1055/s-1997-1173

文献信息

• Glycerol/CuI/Zn as a recyclable catalytic system for synthesis of vinyl sulfides and tellurides
  作者：Lóren C.C. Gonçalves、David B. Lima、Pedro M.Y. Borba、Gelson Perin、Diego Alves、Raquel G. Jacob、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2013.04.119

  日期：2013.6

  Cu-catalyzed coupling of diphenyl disulfide and diphenyl ditelluride with vinyl bromides using a recyclable catalytic system and glycerol as a green solvent is described. This protocol was efficiently used in the preparation of vinyl sulfides and vinyl tellurides with a variety of substituents in good yields and stereoselectively. The solvent/catalyst system was directly reused for four cycles without loss

  描述了一种使用可循环利用的催化体系和甘油作为绿色溶剂的Cu催化的二苯基二硫化物和二苯基二碲化物与乙烯基溴偶联的简便方法。该方案可有效地用于制备具有各种取代基的乙烯基硫化物和碲化乙烯基化合物，且收率高且立体选择性好。溶剂/催化剂体系可直接重复使用四个循环，而不会损失活性。
• A simple and general preparation of vinylic sulfides, selenides and tellurides
  作者：Claudio C. Silveira、Paulo Cesar S. Santos、Samuel R. Mendes、Antonio L. Braga

  DOI：10.1016/j.jorganchem.2008.09.039

  日期：2008.12

  A general method for the synthesis of vinylic chalcogenides by nucleophilic and Ni-catalyzed vinylic substitution on vinylic halides by phenyl chalcogenolates is described. The reactions were regio and stereoselective for the nickel catalyzed substitution, and mixture of isomers was observed for some examples in the thermal process in DMF.

  描述了通过苯基硫属元素化物在乙烯基卤化物上通过亲核和Ni催化的乙烯基取代来合成乙烯基硫属元素化物的一般方法。对于镍催化的取代，该反应是区域性和立体选择性的，并且在DMF的热过程中的一些实例中观察到异构体的混合物。
• Influence of the gegenion in the transmetalation reaction of vinylic tellurides with higher order cyanocuprates
  作者：André Chieffi、João V. Comasseto

  DOI：10.1016/s0040-4039(00)73112-1

  日期：1994.6

  Dilithium cyanocuprates R2LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCHCHTeR1 to give higher order vinylic cyanocuprates, [(RCHCH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross - coupling products of Z configuration, RCHCHR2 in good yields.

  二锂cyanocuprates - [R 2 LCU（CN）栗2（L = 2-Th时，Me）的具有乙烯型碲化物反应Ž配置，RCHCHTeR 1得到高阶乙烯基cyanocuprates，[（RCHCH）LCU（CN）栗2 ]。通过将锗酸根离子从锂变为镁[R 2 LCu（CN）LiMgBr或R 2 LCu（CN）（MgBr）2 ]，该反应以良好的收率得到了Z构型的交联产物RCH = CHR 2。
• Cerium(III)-Mediated Efficient and Stereoselective Hydrochalcogenation of Terminal Alkynes
  作者：Claudio Silveira、Samuel Mendes、Daniel Rosa、Gilson Zeni

  DOI：10.1055/s-0029-1217029

  日期：2009.12

  Vinylic chalcogenides were synthesized stereospecifically by hydrochalcogenation of propargylic amines or alcohols mediated by cerium(III) chloride. The products were obtained in good yields and with high regio- and stereoselectivities. cerium chloride - vinylic chalcogenides - hydrochalcogenation - selenium - tellurium

  乙烯基硫族化物是通过氯化铈（III）介导的炔丙基胺或醇的氢化硫属反应立体定向合成的。以高收率和高区域选择性和立体选择性获得产物。 氯化铈-乙烯基硫属元素化物-加氢硫属化合物-硒-碲
• Phosphine-nickel(II), -cobalt(II), -palladium(0) and -palladium(II) complexes as catalysts in cross-coupling reactions of aryl- and alkyl-grignard reagents with organic tellurides
  作者：Sakae Uemura、Shin-Ichi Fukuzawa、Suresh R. Patil

  DOI：10.1016/0022-328x(83)80215-0

  日期：1983.2

  in good to moderate yields, with elemental tellurium being formed as a black precipitate. A catalytic reduction-oxidation cycle involving a Ni or Co complex bearing an organotellurium moiety (RTe; R  alkenyl, aryl, and alkyl) is proposed for the reaction. Palladium catalysts such as Pd(PPh3)4, PdCl2(PPh3)2, and PdCl2(PhCN)2 are revaled to be much less effective than the Ni and Co catalysts in both the

  在NiCl 2（PPh 3）2，NiCl 2（Ph 2 PCH 2 CH 2 CH 2 PPh 2）或CoCl 2的存在下，一些烷基-和芳基-碲化物与格氏试剂（RMgBr; R芳基和烷基）反应（PPh 3）2在四氢呋喃中作为催化剂或在溶剂中的二乙基酯作为溶剂，以良好至中等的收率得到交叉偶联的产物与碲化物的均相偶联产物，其中元素碲形成为黑色沉淀物。对于该反应，提出了一种催化还原-氧化循环，该循环涉及包含带有有机碲部分（RTe； R 6烯基，芳基和烷基）的Ni或Co配合物。钯催化剂（例如Pd（PPh 3）4，PdCl 2（PPh 3）2和PdCl 2（PhCN）2）的收率和立体选择性均比Ni和Co催化剂差很多。