(Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride | 173439-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride
• 英文别名: Z-(2-cyclohexenyl-1-ethenyl)butyltelluride；1-[(Z)-2-butyltellanylethenyl]cyclohexene
• CAS: 173439-74-2
• 化学式: C₁₂H₂₀Te
• 分子量: 291.891
• InChiKey: LJZURXNZIZMIPG-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  异丙醇频哪醇硼酸酯 、 (Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride 在 正丁基锂 作用下， 以 hexanes 、 乙醚 为溶剂， 以75%的产率得到(Z)-2-(2-(cyclohex-1-en-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

  摘要：

  A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4) (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.06.092
• 作为产物：
  描述：

  1-(2-Butyltellanylethynyl)cyclohexene 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 以47%的产率得到(Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride
  参考文献：
  名称：

  完全控制乙烯基碲化物的区域和立体异构体的合成

  摘要：

  描述了对E，Z或1，1-取代的乙烯基碲化物的合成进行总体控制的方法。还获得在碳2或在碳1上带有丁基或碲构型的碲脲丁二烯，该碲在含碲的双键处具有E或Z构型。在末端炔烃中添加丁基碲铝酸二异丁基铝导致形成1-（丁基teluro）-1-（有机基）乙烯，产率为45％至75％。Al / Te在乙烯基丙氨酸上与丁基碲基溴化物/ LiCl的交换反应以50-60％的收率提供了E构型的异构体。通过乙炔化碲化物的水铝化，可以在30-51％的收率下获得形成双键的Z构型的乙烯基碲化物。

  DOI：

  10.1016/0040-4020(95)00840-5

文献信息

• (1 Z ,3 Z )-Buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1 Z ,3 Z )-butyltelluro-1,3-butadienes and (1 Z ,3 Z )-1,4-bis(butyltelluro)-1,3-butadienes
  作者：Miguel J. Dabdoub、Vania B. Dabdoub、Palimécio G. Guerrero、Claudio C. Silveira

  DOI：10.1016/s0040-4020(97)00148-8

  日期：1997.3

  (1Z,3Z)-1-Butyltelluro-1,3-butadienes 8, 9 and 12 obtained by the hydrotelluration of but-1-en-3-ynes 1, 2 and 5 were transformed into the corresponding buta-1,3-dienyl-1-lithium by reaction with n-BuLi. 1,3-Butadienes 14, 15, 17-20 were obtained with retention of the double bond geometry by reaction of the butadienyllithium intermediates with electrophiles. The butadienyllithium 13 obtained by the Te/Li exchange reaction in the (12,3Z)-1-Butyltelluro-4-methoxy-1,3-Butadiene 8 was reacted with benzaldehyde to form the corresponding alcohol 15 with total retention of configuration, that undergoes hydrolysis resulting into the (E,E)-5-phenyl-2,3-pentadien-1-al 16. Hydrotelluration of the 1-butyltellurobut-1-en-3-cyclization, leading to substituted tellurophenes 24, 25, 27-29 via a sequential Csp(2)-Te and Csp(3)-Te bonds cleavage on reaction with n-BuLi followed by addition of electrophiles. (C) 1997 Elsevier Science Ltd.

  (1Z,3Z)-1-丁基-1,3-丁二烯碲化物8、9和12是通过1-丁-3-炔-1-烯的水合碲化反应获得的，随后通过与n-BuLi的反应转化为相应的1-丁-1,3-二烯基锂。通过将这些丁二烯基锂中间体与电亲核试剂反应，在保留双键几何构型的情况下，得到了1,3-丁二烯14、15和17-20。通过Te/Li交换反应，在(12,3Z)-4-甲氧基-1-丁基-1,3-丁二烯碲化物8的基础上获得了丁二烯基锂13，并与苯甲醛反应形成了保留全部构型的相应醇15，该醇经水解生成(E,E)-5-苯基-2,3-戊二烯-1-醛16。1-丁基-1-烯-3-炔的水合碲化后，通过与n-BuLi的反应依次断裂Csp(2)-Te和Csp(3)-Te键，随后加入电亲核试剂，形成取代的碲代芳香烃24、25、27-29。 (C) 1997 Elsevier Science Ltd.
• Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates
  作者：Miguel J. Dabdoub、Mauro L. Begnini、Palimécio G. Guerrero

  DOI：10.1016/s0040-4020(98)00014-3

  日期：1998.3

  Acetylenic tellurides react with Cp2Zr(H)Cl in THF at room temperature to give the alpha-zirconated vinyl telluride intermediates 39, which react with a wide range of electrophiles to give several types of trisubstituted olefins, such as alpha-halo vinyl tellurides, ketene telluro(seleno) acetals, ketene telluro acetals, and vinylic tellurides of Z configuration. Acetylenic selenides undergo similar reactions, but a lack of regioselectivity results in the formation of a mixture of alpha-zirconated 19 and beta- zirconated 20 vinylic selenide intermediates. After a derailed study was established that the use of 2.0 equivalents of Cp2Zr(H)Cl is crucial to perform the total hydrozirconation of acetylenic selenides or tellurides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Two-Step Regio- and Stereoselective Synthesis of <i>cis</i>-Vinylstannanes
  作者：Paul Malek Mirzayans、Rebecca H. Pouwer、Craig M. Williams

  DOI：10.1021/ol801251m

  日期：2008.9.1

  Herein we describe a novel stereoselective synthesis of cis-vinylstannanes employing the widely established Li/Te exchange pathway. In contrast to previously reported methods of cis-selective hydrostannation (i.e., ZrCl4), this method demonstrates compatibility toward oxygenated substrates.
• Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts
  作者：Hélio A. Stefani、Rodrigo Cella、Felipe A. Dörr、Claudio M.P. Pereira、Gilson Zeni、Marlito Gomes

  DOI：10.1016/j.tetlet.2004.11.160

  日期：2005.1

  The palladium-catalyzed cross-coupling reaction between potassium alkynyltrifluoroborate salts and vinylic tellurides proceeds readily to afford 1,3-enynes with moderate to good yields. (C) 2004 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed cross-coupling of vinylic tellurides and potassium vinyltrifluoroborate salt: synthesis of 1,3-dienes
  作者：Rodrigo Cella、Aline T.G. Orfão、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2006.05.088

  日期：2006.7

  Here we report an ultrasound-assisted synthesis of stereodefined 1,3-dienes by Suzuki-Miyaura cross-coupling reactions of vinylic tellurides and potassium beta-styryl trifluoroborate salt. (c) 2006 Elsevier Ltd. All rights reserved.